General organic and biological chemistry an integrated approach 2

8.2  Constitutional Isomers   283 CH3CH2CH2CH2CH2CH3 CH3CHCH2CH2CH3 ƒ CH3 2ƒ CH3CCH2CH3 CH3 2-Methylpentane ƒ CH3 Hexane CH3CH2CHCH2CH3 3-Methylpentane CH3 3ƒ CH3CHCHCH3 ƒ ƒ CH3 CH3 2,2-Dimethylbutane 2,3-Dimethylbutane In some cases, as is true for the formulas in Figure 8.3, identifying constitutional i­somers is a simple process Their structures look different enough that there is no question that they are constitutional isomers At other times, making this identification can be more difficult For example, although the molecules below might, at first, appear to be different, all structures represent the same molecule, 2-methylhexane It is important to remember that line-bond structures not show the true shape of a molecule, just the bonding arrangements 5 CH3 CH3 CH3CH2CH2CH2CHCH3 CH2CH3 4 CH2CH2CH2 CH2CH2CHCH3 CH3 CH3CH CH3 2-Methylhexane One sure way to decide whether two molecules are identical or are constitutional isomers is to name them Identical molecules have the same IUPAC name and constitutional isomers have different IUPAC names Sample Problem  8.2 Identifying constitutional isomers Are the two alkanes constitutional isomers or are they identical? CH3 CH3CH2 ƒ CH2CHCH3 ƒ CH3 ƒ CH3CH ƒ CH2CH2 ƒ CH3 Strategy Constitutional isomers have the same molecular formula but different structures (and names) Solution Identical molecules They both have the same formula (C6H14) and the same name (2‑methylpentane) Practice Problem  8.2 Are the two alkanes constitutional isomers or are they identical? ■ ■ Figure 8.3 Constitutional isomers of C6H14  The five molecules shown are the constitutional isomers with the molecular formula C6H14 Constitutional isomers always have different names from one another 284   Chapter 8  Organic Reactions 1—Hydrocarbons, Carboxylic Acids, Amines, and Related Compounds Natural gas (C1–C4) Gasoline (C5–C12) Petroleum Diesel and kerosene (C12–C18) Heating oil (C16–C20) Lubricating oil > ( C20) ■ ■Figure 8.4 Petroleum  Petroleum is mostly a mixture of different hydrocarbons Groups of similar-sized molecules are used for different purposes Gasoline is a mixture of hydrocarbons having 5–12 carbon atoms (C5–C12) While on the subject of alkane constitutional isomers, it is worth discussing how we obtain and use some alkanes The natural gas used to heat homes is mostly methane, mixed with smaller amounts of ethane, propane, and butane Propane, by itself, is used as a fuel for camp stoves and barbecues and butane is used in disposable lighters Petroleum (crude oil), a mixture of hydrocarbons and lesser amounts of organic molecules that contain oxygen, nitrogen, and sulfur, is the source of most of the other alkanes that we use (Figure 8.4) Gasoline is a mixture of alkanes having between and 12 carbon atoms, other hydrocarbons, and additional compounds that are added to improve the performance of automobile engines Gasoline contains a greater number of different alkanes than you might expect There being three alkane constitutional isomers with the formula C5H12, five isomers with the formula C6H14, and many more with the formulas C7H16 through C12H26, hundreds of different alkanes can be found in gasoline Other important mixtures of alkanes include diesel fuel (contains alkanes with between 12 and 18 carbon atoms), motor oil (alkanes with more than 15 carbon atoms), and asphalt (alkanes with more than 35 carbon atoms) 8.3 n C o n fo r m a t i o n s Conformations are interchanged by rotation around single bonds When dealing with organic or biomolecules, it is often not enough to know only which constitutional isomer is present Sometimes we must also know something about which of a number of possible three-dimensional shapes a molecule is found in Among other things, the threedimensional shape that a molecule has can affect the transport of certain compounds across cell membranes and the proper functioning of proteins Rotation about single bonds allows most molecules to assume a number of different three-dimensional shapes The shapes that a molecule can take because of bond rotations are called conformations The different conformations of a molecule • have the same molecular formula • have the same atomic connections • have different three-dimensional shapes • are interchanged by the rotation of single bonds Switching from one conformation to another always involves single bond rotation, never bond breaking In the case of butane, pictured in Figure 8.5, three of the many possible conformations resulting from rotations about the bond between carbons and are shown Of these three, the one shown in Figure 8.5c is the most stable (most favored) because it minimizes crowding by placing all of the atoms and bonds as far apart as possible 8.4  Cycloalkanes   285 H H H H H H C H C H H (a) H H C H (b) C H C H C H H H H H (c) C H C H C H H C H H C H H H H ■ ■Figure 8.5 C H Conformations of butane  Rotation about the bond between carbons and in butane gives rise to different conformations (three-dimensional shapes) for the molecule 8.4 C y c l oa l k a n e s In some alkanes, called cycloalkanes, carbon atoms are joined into rings (Figure 8.6) Like their noncyclic counterparts, cycloalkanes are nonpolar molecules that are attracted to one another by London forces To simplify matters, cycloalkanes are usually drawn using skeletal structures, although side views can be useful when considering the orientation of substituents attached to a ring Name Lewis structure H Cyclopropane H C C Side view H H C H Skeletal structure H H H H H H H H Cyclobutane H C C H H C C H H H Cyclopentane H C H C C H H H C C H H H H Cyclohexane H H H C H C H H H C C H C H C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H ■ ■Figure 8.6 Cycloalkanes  Cycloalkanes are alkanes whose carbon atoms are joined in a ring 286   Chapter 8  Organic Reactions 1—Hydrocarbons, Carboxylic Acids, Amines, and Related Compounds When naming cycloalkanes, the ring is usually designated as the parent, which is named by combining “cyclo” with the appropriate numbering prefix (Table 8.2) and “ane.” When only one alkyl group is attached to a cycloalkane parent, the carbon atom that holds that group is carbon (Figure 8.7a), but the number is not included in the name When a ring holds more than one alkyl group, the ring is numbered from the ­position and in the direction that gives the lowest numbers Figure 8.7b shows how this works for the three dimethylcyclopentane constitutional isomers CH3 (a) CH3 (b) H3C CH3 CH3 CH3 CH3 Methylcyclopentane 1,1-Dimethylcyclopentane 1,2-Dimethylcyclopentane 1,3-Dimethylcyclopentane ■ ■Figure 8.7 IUPAC names of cycloalkanes  (a) With one substituent present, the parent ring is numbered starting at the substituent The position number is omitted from the name, however (b) When more than one substituent is present, the parent ring is numbered from the position and in the direction that gives the lowest numbers Geometric Isomers n Stereoisomers are interchanged only by breaking bonds The limited rotation of the carbon–carbon single bonds in cycloalkanes has an interesting side effect in that it allows for the existence of stereoisomers, molecules that • have the same molecular formula • have the same atomic connections • have different three-dimensional shapes • are interchanged only by breaking bonds Except for the last item in the list (are interchanged only by breaking bonds), the description above is identical to that given for conformations (Section 8.3) When stereoisomers exist because of restricted bond rotation, the stereoisomers are called geometric isomers To explore this concept, let us compare the three-dimensional structure of a noncyclic alkane with that of a cycloalkane Figure 8.8a shows two conformations of butane, interchanged by rotation about the carbon–carbon single bond between carbons and The two 1,2-dimethylcyclohexane molecules in Figure 8.8b are stereoisomers Rotation of the ring carbon–carbon bonds is limited, so the molecule that has methyl groups on the same H3C H C H (a) ■ ■Figure 8.8 Geometric isomers  (a) Two conformations of butane are interchanged by single bond rotation (b) Two geometric isomers of 1,2-dimethyl­cyclohexane are interchanged only by bond breaking In cis-1,2-dimethylcycl­o­­hexane the methyl groups are on the same face of the ring In trans-1,2dimethyl­cyclohexane they are on opposite sides H3C CH3 H C H C H H H C H CH3 Butane H (b) H H H CH3 H CH3 H H H H H H H cis -1,2-Dimethylcyclohexane H H H CH3 H H H H H CH3 trans -1,2-Dimethylcyclohexane 8.5  Alkenes, Alkynes, and Aromatic Compounds   287 face of the ring can never be rotated enough to look like the molecule with the methyl groups on opposite faces Transforming one of these molecules into the other requires the breaking of covalent bonds, which makes them geometric isomers Geometric isomers come in pairs—one is cis and one is trans For cycloalkanes, a cis geometric isomer has the two alkyl groups on the same face of the ring and a trans isomer has them on opposite faces Sample Problem  8.3 Identifying isomers Identify each pair as being geometric isomers, constitutional isomers, or identical ­molecules a cis-1,4-dimethylcyclohexane and trans-1,2-dimethylcyclohexane b cis-1,4-dimethylcyclohexane and trans-1,4-dimethylcyclohexane Strategy To solve this problem it will help you to remember that geometric isomers (stereoisomers) have the same molecular formula and atomic connections, while constitutional isomers have the same molecular formula and different atomic connections Solution a Constitutional isomers While cis and trans molecules are geometric isomers, these two molecules are not geometric isomers of the same molecule They are constitutional isomers because they have different atomic connections (1,4-dimethyl versus 1,2‑dimethyl) b Geometric isomers These two molecules have the same atomic connections (both are 1,4-dimethyl), so they are not constitutional isomers They are geometric isomers of 1,4-dimethylcyclohexane Practice Problem  8.3 Draw and name the geometric isomers of 1-ethyl-2-methylcyclohexane 8.5 A l k e n e s , A l k y n e s , a n d A r o m a t i c C o m p o u n d s We have just considered alkanes and cycloalkanes, which are saturated hydrocarbons The term “saturated” indicates that the molecules contain only single-bonded atoms In this section we will take a look at unsaturated hydrocarbons, hydrocarbon molecules that contain double or triple bonds Alkenes contain at least one carbon–carbon double bond In ethylene, the smallest alkene, the carbon atoms carry three groups of electrons—one double bond and two ­single bonds This results in a trigonal planar shape around each carbon atom (Table 4.2) Alkynes contain at least one ­carbon–carbon triple bond and the smallest member of this family is acetylene Each carbon atom in acetylene has two groups of electrons arranged in a ­linear shape H H H¬C‚C¬H C“C H H Ethylene Acetylene n Unsaturated molecules contain double or triple bonds n Alkenes contain carbon–carbon double bonds n Alkynes contain carbon–carbon triple bonds 288   Chapter 8  Organic Reactions 1—Hydrocarbons, Carboxylic Acids, Amines, and Related Compounds ■ ■Figure 8.9 H Muscalure  This alkene, produced by the female housefly, is a pheromone (a chemical messenger) that is used to attract a mate H C“C CH3(CH2)6CH2 CH2(CH2)11CH3 Muscalure Some alkenes and alkynes can be obtained from petroleum, but many are produced by living things The alkene called muscalure is a sex-attractant pheromone (chemical messenger) produced by houseflies (Figure 8.9) The third family of unsaturated hydrocarbons is aromatic hydrocarbons A well-known member of this family, benzene, is a ring of six carbon atoms that can be drawn with each carbon atom having one single and one double bond to neighboring carbon atoms, and one bond to a hydrogen atom H H H C C C C C C H H H Benzene Although the double bonds give benzene the appearance of being an alkene, it and other aromatic compounds not behave as alkenes To de-emphasize their alkene-like appearance, aromatic compounds are often drawn with a circle replacing the double bonds Like alkanes, the unsaturated hydrocarbons (alkenes, alkynes, and aromatic compounds) contain only nonpolar covalent bonds and are nonpolar molecules London forces hold members of these hydrocarbon families to one another, and increasing size leads to stronger London force attractions between molecules and higher melting and boiling points (Table 8.1) Naming When using the IUPAC rules to name alkenes or alkynes, the parent is the longest chain of carbon atoms that has the carbon–carbon double or triple bond Numbering of the parent begins at the end nearer the double or triple bond, and the position of the bond is indicated using the lower number assigned to the multiply bonded carbon atoms As with naming alkanes, the ending on the name indicates the organic family—IUPAC names of alkenes end with “ene” and those of alkynes end with “yne.” Once the parent chain has been determined, alkyl groups are identified by name, position, and number of appearances (Figure 8.10a) Sometimes an organic compound is known by its common name, a name that is not assigned according to the IUPAC rules Ethylene (for ethene), propylene (for propene), and acetylene (for ethyne) are examples “Benzene” is an accepted IUPAC name, so benzene-related compounds are named using benzene as the parent ring When only one substituent is attached, its position is not specified in the name, as is the case for methylbenzene (Figure 8.10b) In the presence of more than one substituent, the ring is numbered from the position and in the direction to give the lowest substituent numbers possible Methylbenzene and 1,2-dimethylbenzene are also known, respectively, by the common names toluene and ortho-xylene For common names of ­benzene-based compounds that have only two substituents attached to the ring, ortho or o refers to a 1,2 arrangement, meta or m to a 1,3 arrangement, and para or p to a 1,4 arrangement An aromatic ring may be part of a larger molecule, so not all aromatic compounds are pure hydrocarbons Examples include benzyl alcohol, benzaldehyde, and benzoic acid Some aromatic compounds, called polycyclic aromatic hydrocarbons (PAHs), contain benzene rings that are fused to one another (they share atoms and bonds) Naphthalene 8.5  Alkenes, Alkynes, and Aromatic Compounds   289 (a) CH2 CHCH2CHCH3 CH3 ■ ■Figure 8.10 CH3 CH3CHCH2CH CHCH2CH2CH3 4-Methyl-1-pentene 2-Methyl-4-octene CH3 CH3CHCHC CH CH3 CH3CHCH3 CH3C CCH2CHCH2CH2CH3 3,4-Dimethyl-1-pentyne (b) CH3 5-Isopropyl-2-octyne CH3 CH3 CH3 CH3 Benzene Methylbenzene (toluene) 1,2-Dimethylbenzene (o-xylene) O O CH2OH CH3 CH3 1,4-Dimethylbenzene (p-xylene) Benzyl alcohol C 1,3-Dimethylbenzene (m-xylene) H Benzaldehyde C OH Naming unsaturated ­hydrocarbons  (a) Alkenes and alkynes When assigning IUPAC names, parent chains, which must contain the carbon– carbon double or triple bond, are numbered from the end nearer these groups For alkenes and alkynes containing two or three carbon atoms, the position of the double or triple bond is not specified Alkene names end in “ene” and alkyne names end in “yne.” (b) Aromatic compounds Methylbenzene is also known as toluene In common names, a 1,2 arrangement of substituents on a benzene ring is an ortho arrangement and dimethylbenzenes are called xylene, so 1,2-dimethylbenzene is orthoxylene or o-xylene Benzyl alcohol, benzaldehyde, and benzoic acid are aromatic compounds that are not pure hydrocarbons Benzoic acid and anthracene (Table 8.1), and phenanthrene (Figure 8.11), all of which can be obtained from coal, are simple examples Benzo[a]pyrene, a large PAH formed during the burning of tobacco, coal, gasoline, and many other substances, is known to cause cancer Geometric Isomers Unlike single bonds, which rotate freely (except when they are in rings; see Section 8.4), double bonds cannot rotate With this restricted bond rotation comes the possibility of some alkenes existing as cis and trans stereoisomers In Figure 8.12a, the two geometric ­isomers of 2-butene are shown In the cis isomer, the two methyl groups ( i CH3) are on the same side of a line connecting the two double-bonded carbon atoms, and in the trans isomer these groups are on opposite sides of that line ■ ■Figure 8.11 Polycyclic aromatic ­hydrocarbons  Phenanthrene, Phenanthrene Benzo[a] pyrene benzo[a]pyrene, and other PAHs contain fused benzene rings 290   Chapter 8  Organic Reactions 1—Hydrocarbons, Carboxylic Acids, Amines, and Related Compounds H (a) H C H C H3C CH3 H3C cis -2-Butene H 3C (b) H C H3C (c) C H H3C H C H3C trans-2-Butene C H 3C H C C CH2CH3 cis -2-Pentene C CH2CH3 H trans-2-Pentene CH3 C CH3 H CH3 C H3C C H 2-Methyl-2-butene ■ ■Figure 8.12 Geometric isomers of alkenes  (a) In the cis isomer the i CH3 groups are on the same side of a line that connects the two double-bonded carbon atoms, and in the trans isomer they are on opposite sides (b) 2-Methyl-2-butene has no cis or trans isomers, because the double-bonded carbon atom on the left is attached to identical groups of atoms ( i CH3 groups) When flipped top to bottom, the molecule on the right is the same as the one on the left (c) In the cis isomer of 2-pentene, the alkyl groups are on the same side of the double bond Not all alkenes are found as cis and trans isomers For geometric isomers to exist, neither carbon atom of the double bond may carry two identical attached atoms or groups of atoms The alkene in Figure 8.12b, 2-methyl-2-butene, has two identical groups ( i CH3) attached to the carbon atom to the left side of the double bond If the molecule drawn on the right is flipped top to bottom, it is identical to the one on the left and cis and trans isomers not exist In Figure 8.12c each of the carbons in the double bond has two different atoms or groups of atoms attached to it If flipped, the 2-pentene on the right cannot be superimposed on the molecule to the left—this alkene has cis and trans isomers Alkynes, having a linear shape across the carbon–carbon triple bond, not exist as cis and trans isomers Sample Problem  8.4 Identifying geometric isomers Which geometric isomer of muscalure is shown in Figure 8.9? Strategy To distinguish the cis from the trans isomer, compare the relative positions of the carbon atoms attached to the carbon–carbon double bond Solution The cis isomer Both ends of the carbon chain are on the same side of a line that connects the double-bonded carbon atoms Practice Problem   8.4 Designate each of the carbon–carbon double bonds in bombykol, a moth pheromone, as cis or trans OH Bombykol 8.6  Reactions of Hydrocarbons   291 8.6 RE A C TI O NS O F HYDR O C A R B O NS Organic compounds are grouped into families based on their structure Alkenes, for example, have a carbon–carbon double bond and alkynes have a carbon–carbon triple bond One reason for learning to identify organic families is that each is connected to a particular set of chemical reactions In this section we will take a look at a few of the important reactions of alkanes, alkenes, alkynes, and aromatic compounds Some of these reactions were introduced in Chapter Alkanes Combustion One of the reactions often carried out on alkanes is that of combustion (Section 5.4) In this reaction an alkane reacts with oxygen gas (O2) to produce carbon dioxide (CO2) and water Combustion, or burning, is also accompanied by the rapid release of heat Examples include burning methane to heat a home and propane to cook food on a grill CH4(g) + 2O2(g) ¡ CO2(g) + 2H2O(g) Methane C3H8(g) + 5O2(g) ¡ 3CO2(g) + 4H2O(g) Ethane Combustion is not just a reaction of alkanes Many other organic compounds can be burned, including the alkyne called acetylene (used in welding) and ethyl alcohol (present in gasohol) 2C2H2(g) + 5O2(g) ¡ 4CO2(g) + 2H2O(g) Acetylene 2C2H6O(l ) + 6O2(g) ¡ 4CO2(g) + 6H2O(g) Ethyl alcohol Halogenation Another important reaction of alkanes is halogenation, in which a chlorine or bromine atom replaces a hydrogen atom on an alkane In this light-initiated halogenation reaction, Cl2 and Br2 are used as reactants and the products are alkyl halides (Section 4.4) plus either HCl or HBr Note that although the Cl2 and Br2 reactants in this substitution reaction (one atom or group replaces another) contain two halogen atoms, just one halogen atom substitutes for one hydrogen atom H H ƒ H¬ C ¬H ± Cl2 light ƒ ƒ H H H H ƒ ƒ ƒ ƒ ƒ H¬ C ¬ Cl ± HCl H H H¬ C ¬ C ¬H ± Br2 H H light ƒ ƒ ƒ ƒ H¬ C ¬ C ¬ Br ± HBr H H Each of the reactions above produces only one halogenation product; CH4 becomes CH3Cl and CH3CH3 becomes CH3CH2Br Depending on its structure, an alkane may yield more than one halogenation product and the products will be constitutional isomers In the examples below, the reaction equations are written in the abbreviated organic style: They are not balanced and some reactants (Cl2 and Br2 in this case) and conditions (light) are written above or below the reaction arrow Cl CH3CH2CH3 Cl2 light CH3CH2CH2Cl and ƒ CH3CHCH3 Br CH3CH2CH2CH3 Br2 light CH3CH2CH2CH2Br and ƒ CH3CH2CHCH3 292   Chapter 8  Organic Reactions 1—Hydrocarbons, Carboxylic Acids, Amines, and Related Compounds This light-initiated halogenation reaction will also take place with other types of ­ olecules The limitation is that only hydrogen atoms attached to alkane-type carbons m (Section 4.4) can be replaced Note that in each reaction below, one halogen atom replaces one hydrogen atom H H ƒ Cl2 ƒ light H¬ C ¬Cl ƒ H¬ C ¬ Cl ƒ H Cl H H ƒ Br2 ƒ light H¬ C “ C ¬ C ¬H ƒ ƒ ƒ H¬ C “ C ¬ C ¬ Br ƒ H H H ƒ ƒ H H H The halogenation of alkanes is important for a couple of reasons First, the alkyl halide products of halogenation reactions have many uses, including CH3Br (an insecticide), CH3Cl (a refrigerant), CH2Cl2 (once used as a solvent for decaffeinating coffee beans), and CHCl3 (once used as an anesthetic) To organic chemists, the other significance of halogenation is that the alkyl halide products can be used in the production of many other compounds In Chapter we will see how alkyl halides can be converted into alcohols, ethers, thiols, and sulfides Some halogenated compounds are found in nature, although their mode of production is enzyme-catalyzed and does not involve a light-initiated reaction Forest fires and volcanic action produce CH3Cl, termites make CHCl3, and rapeseed plants (a source of canola oil) release CH3Br Many complex molecules have been isolated from marine plants and animals (Figure 8.13) O CH3CH2CHCH“CH ƒ Br Br O ClCH2CH2 Cl ƒ CHCH2CH“CHC‚CH Cl Cl HO CH3 OH NH O CH OH O ■ ■FIGURE 8.13 Halogenated compounds present in marine species  Some halogenated compounds occur naturally Many, including those shown here, are isolated from members of various marine species SAMPLE PROBLEM  8.5 Halogenation When 2-methylpropane reacts with Cl2 in the presence of light, two halogenation products are formed Cl Cl2 CH3CHCH3 light ƒ CH3 and CH3CHCH2Cl ƒ ƒ CH3CCH3 CH3 ƒ CH3 Are these two products the only constitutional isomers that form, or are the two compounds below additional products? CH3CHCH3 ƒ CH2Cl and ClCH2CHCH3 ƒ CH3 Strategy To answer this problem, you must decide whether these two compounds are the same as or different from the two products that were originally drawn 646     Appendix D Pentose  A monosaccharide that contains five carbon atoms Pentose phosphate pathway  A metabolic pathway involved in the production of ribose, 2-deoxyribose, other 3-, 4-, 5-, 6-, and 7-carbon sugar molecules, and NADPH Peptide  A general name given to oligo- and polypeptides Peptide bond  Another name for the amide bond that connects amino acid residues in a peptide or a protein Percent yield  actual yield * 100     percent yield = theoretical yield Period  Elements in the same horizontal row of the periodic table Periodic table of the elements  A complete list of the elements arranged in order from smallest to  largest atomic number, with elements having similar properties placed in the same group pH  pH = -log[H3O+] pH optimum  The pH at which an enzyme is most active Phenol  An organic compound that contains a hydroxyl group which is attached to an aromatic ring Phospholipid  A class of lipids whose members contain a phosphate residue Physical change  A change in matter that does not involve varying its chemical composition Physical property  A characteristic of matter that can be determined without changing its chemical composition pI  See isoelectric point pKa  pKa = -logKa, where Ka is an acidity constant Plane-polarized light  Light that has been passed through a filter that blocks all light waves except those vibrating in one particular orientation (plane) Polar-acidic amino acid  An amino acid whose side chain contains a carboxyl group Polar-basic amino acid  An amino acid whose side chain contains an amino group or another basic ­nitrogen-containing group Polar covalent bond  A covalent bond in which bonding electrons are unequally shared Polar molecule  A molecule in which one side has a partial positive charge and the other has a partial negative charge Polar-neutral amino acid  An amino acid whose side chain is polar and neutral, typically an alcohol, a phenol, or an amide Polyatomic ion  An ion consisting of two or more atoms Polycyclic aromatic hydrocarbon  An aromatic compound that contains benzene rings that are fused to one another ­(carbon–carbon bonds are shared by one or more rings) Polymerase chain reaction  (PCR) A laboratory technique in which desired portions of DNA are replicated over and over Polynucleotide  A compound consisting of more than ten nucleotide residues Polypeptide  A compound consisting of more than ten amino acid residues Polypeptide backbone  The series of alternating alpha carbon atoms and peptide groups present in a polypeptide Polysaccharide  A compound consisting of more than ten monosaccharide residues Polyunsaturated fatty acid  A fatty acid whose hydrocarbon tail has more than one carbon–carbon double bond Positive effector  An allosteric effector that enhances substrate binding and increases the rate of an enzyme-catalyzed reaction Positron  (01 b) A form of nuclear radiation that consists of a positively charged ­electron Post-transcriptional modification  Changes made to RNA after its formation during transcription Post-translational modification  Changes made to a peptide after its formation during translation Potential energy  Stored energy ppb  See parts per billion ppm  See parts per million ppt  See parts per thousand Precipitate  A solid formed during a chemical reaction Precision  A measure of how close repeated measurements are to one another Pressure  The force of the collisions that take place between the particles of a gas and an object Primary  This term can be used to describe the structure of amines and alcohols In a primary (1°) amine the nitrogen atom is attached to only one carbon atom In a primary alcohol the carbon atom carrying the i OH is attached to only one other carbon atom Primary structure  When applied to proteins, primary structure is the sequence of amino acid residues When applied to oligo- or polynucleotides, primary ­structure is the sequence of deoxyribonucleotide (in DNA) or ribonucleotide (in RNA) residues Product  A substance formed during a reaction Promoter site  A site on DNA where transcription begins Prosthetic group  A nonpeptide component that contributes to protein tertiary ­structure Protein  A polypeptide containing more than fifty amino acid residues Proton  A subatomic particle found in the nucleus of an atom Protons carry a charge of 11 and have a mass of about amu Pure substance  A substance that consists of just one element or compound Pyramidal shape  An arrangement of atoms in which one atom can be imagined as being placed at the center of a tetrahedron and the three atoms to which it is attached placed at three of the corners of the same tetrahedron Pyranose  An anomer that contains a sixmembered ring (one oxygen atom and five carbon atoms) Quantum mechanics  A theory that views electrons as residing in atomic orbitals Quaternary  This term can be used to describe derivatives of ammonium ions In a quaternary (4°) ammonium ion the nitrogen atom is attached to four carbon atoms and has a positive charge Quaternary structure  The combination of two or more polypeptide chains to form a functioning protein Racemic mixture  A 50:50 mixture of enantiomers Rad  A radioactivity unit based on the amount of energy absorbed rad is a dose of 0.01 J/kg of the mass of the object Radioactive isotope  (radioisotope) An atom that releases nuclear radiation Radioisotope  See radioactive isotope RDA  See recommended dietary allowance Reactant  A substance present at the start of a reaction Reaction energy diagram  A diagram that shows energy on the y-axis and reaction progress (with reactants on the left and products on the right) on the x-axis Reaction rate  A measure of the speed with which reaction products form Recombinant DNA  A DNA molecule that contains DNA from more than one source Recommended Dietary Allowance  The daily intake of nutrients sufficient to meet the needs of 97% to 98% of healthy people Reducing agent  A reactant that reduces (adds electrons to) another reactant Appendix D     647 Reducing sugar  A carbohydrate that reacts with (is oxidized by) Benedict’s reagent Reduction  The gain of electrons Relative specificity  Restriction of the activity of an enzyme to a range of substrates with the same functional group or similar structure Rem  A radioactivity unit that takes biological effects into account rem equals the dose in rads multiplied by a factor related to the type of radioactivity Replication  A process, known also as DNA replication, that involves using existing DNA as a template for the production of new DNA molecules Replication fork  The place, at either end of an origin, where replication takes place Representative elements  Elements belonging to groups 1A–8A Residue  That part of a reactant molecule that remains when it has been incorporated into a larger structure Reverse transcription  A process in which the primary structure of RNA is used as a template for the production of DNA Reversible inhibitor  An enzyme inhibitor whose effect is not permanent (is reversible) because the inhibitor is loosely bound to the enzyme and can dissociate, restoring the enzyme to its original state Ribonucleic acid  (RNA) An oligo- or polynucleotide built from nucleotides that contain ribose and the bases adenine, guanine, cytosine, and uracil Ribonucleoside  A nucleoside that contains a ribose residue Ribonucleotide  A nucleotide that contains a ribose residue Ribosomal RNA  (rRNA) The form of RNA that combines with proteins to form ­ribosomes Ribosome  A multi-subunit complex composed of rRNA and proteins, where protein synthesis takes place RNA  See ribonucleic acid RNA polymerase  An enzyme that catalyzes the formation of RNA rRNA  See ribosomal RNA Saponification  Hydrolysis of an ester in the presence of aqueous NaOH Saturated fatty acid  A fatty acid whose hydrocarbon tail contains only singlebonded carbon atoms Saturated hydrocarbon  A hydrocarbon that contains only single-bonded carbon atoms Saturated solution  A solution that holds the most solute possible at a particular temperature Scientific method  A process used to gather and interpret information about the world around us Observation, experiment, and the development of laws, hypotheses, and theories are part of the scientific method Scientific notation  Notation in which values are written as a number between and 10 multiplied by a power of ten Secondary  This term can be used to describe the structure of amines and alcohols In a secondary (2°) amine the nitrogen atom is attached to only two carbon atoms In a secondary alcohol the carbon atom carrying the i OH is attached to only two other carbon atoms Secondary structure  When applied to proteins, secondary structure is the folding of the chain that results from hydrogen bonding that takes place between amide N i H and amide C “ O groups from different parts of the polypeptide chain Two common forms of secondary structure are the a-helix and the b-sheet When applied to polynucleotides, secondary structure is the helix formed by the interaction of two DNA strands Seivert  A radioactivity unit that takes biological effects into account seivert (Sv) equals 100 rem Semiconservative replication  DNA replication in which each of the two new DNA molecules contains one strand of the original DNA Semimetal  An element that has physical properties that are intermediate between those of metals and nonmetals Semimetals are also known as metalloids Sex hormone  A steroid hormone that controls the development of secondary sexual characteristics Short tandem repeats  (STRs) Short stretches of noncoding DNA that contain repeating sequences of bases SI system  A measurement system that uses the kilogram, the cubic meter, and the meter to measure, respectively, mass, volume, and length Significant figures  Digits in a measurement that are reproducible when the measurement is repeated, plus the first doubtful digit Simple protein  A protein that does not require a prosthetic group for biological activity Single bond  One pair of electrons shared by two atoms Single replacement reaction  A reaction in which one element replaces another element in a compound Skeletal structure  An abbreviated structural formula that represents covalent bonds by lines, does not show carbon atoms, and shows hydrogen atoms only when they are attached to atoms other than carbon Solid  The form of matter that has a fixed shape and volume Solubility  A measure of the amount of solute that will dissolve in a solvent at a given temperature Soluble  Able to dissolve in (form a homogeneous mixture with) a given solute Solute  A solution component that is present in a lesser amount than the solvent Solution  Another name for a homogeneous mixture Solvent  The solution component that is present in the greatest amount Specific gravity  The density of a substance divided by the density of water at the same temperature Specific heat  The amount of heat required to raise the temperature of one gram of a substance by 1°C Spectator ion  An ion that appears identically on both sides of an ionic equation Sphingolipid  A class of lipids whose members contain a sphingosine residue Sphygmomanometer  A device, consisting of an inflatable cuff attached to a manometer, that is used to measure blood pressure Spiral metabolic pathway  A metabolic pathway consisting of a series of repeated reactions that are used to break down or produce a compound Spontaneous reaction  A reaction that continues to occur once it has been started Standard temperature and pressure  (STP) A temperature of 0°C and a pressure of atm Stereoisomers  Molecules that have the same molecular formula, the same atomic connections, different three-dimensional shapes, and are interchanged only by breaking bonds Stereospecificity  Restriction of the activity of an enzyme to catalyzing the reaction of only one particular stereoisomer of a substrate or formation of only one stereoisomer of a product Steroid  A class of lipids that share the same basic ring structure: three fused 6-carbon atom rings and one 5-carbon atom ring STP  See standard temperature and pressure STR  See short tandem repeats Structural formula  A formula that shows which atoms are present in a compound and how they are connected to one another 648     Appendix D Subatomic particle  A particle of matter that is smaller than an atom Protons, neutrons, and electrons are the subatomic particles present in atoms Sublimation  The conversion of a solid into a gas, bypassing the liquid phase Substituent  An atom or group of atoms attached to the parent chain of an organic molecule Substitution reaction  A reaction in which one atom or group of atoms replaces a different atom or group of atoms Substrate  The reactant in an ­enzyme-catalyzed reaction Sugar–phosphate backbone  The portion of structure of oligo- and polynucleotides that consists of repeating units of phosphate attached to 2-deoxyribose (in DNA) or ribose (in RNA), attached to phosphate, and so on Sulfide  An organic compound that contains a C i S i C linkage Supercoiling  The twisting or coiling of a DNA double helix into a tighter, more compact shape Suspension  A mixture that consists of particles suspended in a liquid Upon standing, the particles will settle Sv  See seivert Synthesis reaction  A reaction in which two or more elements or compounds combine to form one more complex compound Temperature optimum  The temperature at which an enzyme is most catalytically active Template strand  The strand of doublestranded DNA that RNA polymerase uses as a template to produce RNA Termination  The last step in translation Once a protein has been synthesized it leaves the ribosome, which dissociates Termination sequence  A series of bases on DNA that indicates where transcription should end Tertiary  This term can be used to describe the structure of amines and alcohols In a tertiary (3°) amine the nitrogen atom is attached to three carbon atoms In a tertiary alcohol the carbon atom carrying the i OH is attached to three other carbon atoms Tertiary structure  Tertiary structure is the overall three-dimensional shape of a protein or a polynucleotide, including the contribution of secondary structure Tetrahedral shape  An arrangement of atoms in which one atom can be imag- ined as being placed at the center of a tetrahedron and the four atoms to which it is attached placed at the four corners of the same tetrahedron Tetrapeptide  An oligopeptide that contains four amino acid residues Tetrose  A monosaccharide that consists of four carbon atoms Theoretical yield  The theoretical maximum amount of product that can be obtained from a reaction Theory  An experimentally tested explanation of an observed behavior A theory is consistent with existing experimental evidence and can be used to make predictions Thiol  An organic compound that contains an i SH group Titration  A process used to determine the concentration of an acid or base solution Tolerable Upper Intake  (UL) The greatest amount of a nutrient that can be safely consumed each day Torr  A unit of pressure   760 torr = atm = 14.7 psi.  Trace element  An element required by the body in small amounts Trans  One of two possible geometric (cistrans) isomers For cycloalkanes, a trans geometric isomer has two substituents on opposite faces of the ring For alkenes, a trans isomer has alkyl groups on opposite sides of a line connecting the two doublebonded carbon atoms Transamination  A reaction of amino acid metabolism in which an amino group from an amino acid is transferred to an a-keto acid, producing a new a-keto acid and a new amino acid Transcription  A process that involves using part of the primary structure of DNA as a template for the production of RNA Transfer RNA  (tRNA) The form of RNA that transports amino acid residues to the site of protein synthesis Transition metals  Elements belonging to groups 1B–8B Translation  A process in which the primary structure of mRNA is used as a template for the production of a protein Triacylglyceride  see triglyceride Triglyceride  A triester composed of three fatty acid residues and a glycerol residue Trigonal planar  An arrangement of atoms in which one atom can be imagined as being placed at the center of an equilateral triangle and the three atoms to which it is attached placed at the three corners of the same triangle Triose  A monosaccharide that consists of three carbon atoms Tripeptide  An oligopeptide that consists of three amino acid residues Triple bond  Three pairs of electrons shared by two atoms Triplet code  See genetic code tRNA  See transfer RNA UL  See tolerable upper intake Unit  A quantity used as a standard of measurement Unit conversion  Changing how a value is expressed by switching from one unit into another Unsaturated hydrocarbon  A hydrocarbon that contains double or triple bonds Unsaturated solution  A solution that holds less than the amount of solute required to produce a saturated solution Uronic acid  An aldose in which the alcohol group at the end of the molecule opposite the aldehyde group has been oxidized to form a carboxylic acid Valence electron  An electron held in an atom’s valence shell Valence shell  An atom’s highest numbered energy level that holds electrons Vapor pressure  The maximum pressure exerted by a gas formed by evaporation of a liquid Vmax  The maximum velocity (reaction rate) that a given concentration of enzyme can produce Vmax is related to the second step in the reaction catalyzed by a Michaelis– Menten enzyme: ES ¡ E + P Wax  A lipid that is a mixture of water insoluble compounds Wax esters, which typically contain 14–36 carbon fatty acid residues and 16–30 carbon alcohol residues, are a major constituent of waxes Weight/volume percent  A concentration unit defined as follows:     weight/volume percent = g of solute * 100 mL of solution Work  A form of energy involved with making changes to matter Zwitterion  The form of an amino acid that carries one positive and one negative charge Zymogen  An inactive enzyme precursor Index Absolute specificity, definition, 478 Accuracy, definition, 15–16 Acesulfame-K, structure and properties of, 398, 399 Acetals, 352–354 formation of, 353–354, 358 glycosides, 390 Acetaminophen poisoning, 116, 141 Acetic acid as buffer, 261 solubility of, 213 structure and properties of, 297 Acetoacetate, from fatty acid catabolism, 569–570 Acetylcholinesterase, as catalyst, 480 Acetyl-CoA in citric acid cycle, 560–562 in glycolysis, 555 in lipid catabolism, 566–569 in metabolism, 544 Acetylene, 132 combustion of, 164, 291 structure of, 287 N-Acetyl-D-galactosamine, in polysaccharides, 404 N-Acetyl-D-glucosamine in polysaccharides, 402 structure of, 382 N-Acetyl-p-benzoquinone imine (NAPQI), 141 Acid(s) acid/base disorders, 264–266 alpha hydroxy, 306–307 Brønsted-Lowry definition, 241 buffers and, 261–267 carboxylic, 301–306 characteristics of, 240 common, 240 conjugate, 242, 302–303, 311 equilibrium and, 243–249 equilibrium constants, 243–246 neutralization of, 257–259 pH effects on concentrations, 259–261 pH scale and, 251–254 properties of, 240 strength of, 254–257 water as, 242, 250 Acidity constant (Ka ), 254–255 Acidosis, definition, 264–266 causes and mechanisms, 264–266 enzyme activity and, 481 Actinide elements, 56 Activation energy, definition, 175 and reaction rates, 175–176 Active sites, substrate attachment to, 480 Active transport, definition, 448 in electron transport chain, 563–564 phospholipids and, 438 principles of, 448 Actual yield, 173 Acyl carrier protein (ACP), in lipid anabolism, 570–571 Acyl homoserine lactones (AHLs), and biofilms, 315 Adenine (A), structure of, 309, 501 Adenosine, structure of, 502 Adenosine 3´, 5´-cyclic monophosphate (cAMP), structure of, 505 Adenosine 5´-diphosphate (ADP) in ATP formation, 542–543 in metabolism, 544, 546, 554 structure of, 505 Adenosine 5´-monophosphate (AMP), in metabolism, 544, 554 Adenosine 5´-triphosphate (ATP) in anabolism, 544–546 in catabolism, 544–546 in citric acid cycle, 561–562 formation of, 542–543, 551–556, 562–565 in gluconeogenesis, 556–558 in glycolysis, 551–556 oxidative phosphorylation and, 562–565 role in metabolism, 544–546 rotenone and, 574 structure of, 505 Adequate Intake (AI), 48 ADH (antidiuretic hormone), 27 Adipocytes, 431 Adrenaline See Epinephrine Adrenocorticoid hormones, structures and properties of, 443, 444 Aerobic conditions, metabolic processes in, 555 Alanine (Ala) in collagen, 475 structure of, 460, 463 Alcohol(s) boiling points of, 337 classification of, 336–337 dehydration of, 159, 343–344, 358 ester reactions and, 304–306 in nature, 135 oxidation of, 341–342, 358 in phospholipids, 438 preparation of, 339–341 properties of, 336–339 reactions with aldehydes and ketones, 352–354, 358 solubility of, 212 structure and characteristics of, 134, 336–339 in waxes, 427–428 Alcohol dehydrogenase, 348 specificity of, 478 Alcoholic fermentation, process of, 555 Alcohol sugars, definition, 382 reactions of, 384 Aldehyde(s) oxidation of, 347–348, 358 physical properties of, 344–346 reactions of and hemiacetal formation, 352, 358 reduction of, 349–351, 358 structure and characteristics of, 136, 138, 344–346 Aldehyde dehydrogenase, 348 in ethanol metabolism, 342, 349 Aldehydes catalytic reduction of, 165 Aldohexoses anomers of, 388 classification of, 372 stereoisomers of, 380 Aldonic acid, definition, 382 Aldopentose, classification of, 373 Aldoses and Benedict’s reagent, 384 classification of, 372, 373 Aldotrioses, classification of, 373 Alkali metals, 56 Alkaline earth metals, 56 Alkalosis causes and mechanisms, 266–267 enzyme activity and, 481 Alkanes, definition, 132 cycloalkanes, 285–287 isomers of, 282–284 IUPAC naming rules, 279–282, 286 normal, 278 physical properties of, 138, 278–279, 337 reactions of, 291–293, 319 solubility of, 212 structure of, 138, 278–279 Alkane-type carbon atom, 134 Alkenes hydration/dehydration reactions and, 159 isomers of, 289–290 naming of, 288–289 reactions of, 159, 293–295, 319 structures and properties of, 132, 138, 287–288 Alkyl groups in alkanes, 279–280 formulas and names of, 280 Alkyl halides in alcohol production, 339–340 common names of, 340 structure and characteristics of, 135–136, 138 Alkynes naming of, 288–289 reactions of, 293–295 structures and properties of, 132– 133, 138, 287–288 Allergens/allergies histamine release in, 276, 316, 490 role of proteins in, 458, 490 Allopurinol gout treatment, 190, 228 inhibitor action of, 484 Allosteric effectors actions of, 487, 505 in citric acid cycle, 561–562 in glycolysis, 552–554 Allosteric enzymes in metabolism, 505, 551–554, 561–562 properties of, 487 Alpha () anomers, definition, 387 -helix, of protein structure, 470–471 Alpha hydroxy acids, exfoliation and, 306–307 -keto acids in transamination, 571–572 Alpha particles, definition, 68 in nuclear reactions, 68–70 shielding from, 73–74 ALS (amyotrophic lateral sclerosis), 351 Amalgam, 105 Amide(s) from carboxylic acids, 320 hydrolysis of, 314–315, 320, 465 structures and properties of, 137, 139, 313–314 Amine(s) classification of, 307–308 in nucleotides, 501–503 pH and, 260–261 properties of, 309–310 structure and characteristics of, 135, 138 structure of, 307–310 as weak organic bases, 311–312, 320 Amino acids, definition, 460 alpha, 460–462 anabolism of, 572–573 catabolism of, 546–547, 571–572 classification of, 463 and genetic code, 518–520 peptide bonds and, 464–467 pH and, 260–261, 462 in protein digestion, 549–550 solubility of, 213 stereoisomers of, 463–464 Amino group (—NH2 ) in amino acid metabolism, 571–572 in amino acids, 460–467 Amino sugars, definition, 382 Ammonia, formation reaction, 171 Ammonium ions, excretion of, 571–572 Amphetamine, structure and functions of, 310–311 Amphipathic compounds and blood type, 395–396 in cell membranes, 437, 447 and denaturation, 477 hormones, lipids, 442 saponification and, 431 solubility of, 213–215 Amphoteric compounds, definition, 242 water as, 242, 250 Amylase(s), in starch digestion, 401, 548–549 Amylopectin digestion of, 549, 550 structure and properties of, 401, 403 Amylose digestion of, 548–550 structure and properties of, 401, 403 Amyotrophic lateral sclerosis (ALS), enzyme role in, 351 Anabolic steroids, effects of, 444, 445, 449 Anabolism See also Catabolism, definition, 543 amino acid, 572–573 characteristics of, 547–548 energy and, 544–546 fatty acid, 570–571 Anaerobic conditions, definition, 555 gluconeogenesis and, 556–558 Androstenedione, properties of, 53, 445 Anesthetics, local, 159 Angioplasty, 77–78 Anions, definition, 92 in ionic compound formation, 97 Anomers, definition, 387 naming of, 387 of sugars, 387–390 Antacids, acid/base effects of, 238, 266, 267 Anthracene, 289 Antibodies, 476 Anticodons, in genetic code, 519 Antidiuretic hormone (ADH), 27 Antifreeze (ethylene glycol), 348 Antigens blood, 395–396 immune system response to, 476      I-1 I-2     index Antihistamines, 276 Antiparallel, in protein structure, 470 Antiseptics, oxidizing agents, 166 Antithrombin, for blood clotting disorder, 498, 532 Aquaporins, in facilitated diffusion, 448 Arachidonic acid, 426 Arginine (Arg) in collagen, 475 as essential amino acid, 573 structure of, 461 Aromatic compounds See also Phenol(s) halogenated, 296–297 polycyclic aromatic hydrocarbons (PAHs), 288–289 reactions of, 295–297 in sunscreens, 139 Aromatic halogenation, 295–296, 297, 319 Aromatic hydrocarbons naming of, 288–289 structures and properties of, 132, 138, 287–288 Aromatic substitution reaction, 295–297 Arrhenius, definition of acids/bases, 241 Arsenic, in drinking water, 80 Artificial sweeteners, 397–399, 400–401 Asparagine (Asn) leukemia and, 489 properties of, 377, 463 structure of, 461 Aspartame, 314 and phenylketonuria, 151, 178 structure and properties of, 398, 399, 469 Aspartate, in NADH shuttle, 564 Aspartic acid (Asp), structure of, 461, 463 Aspirin inhibition activity of, 484 properties of, 447 structural formula of, 123 Atherosclerosis, characteristics of, 442 Atmospheric pressure, 192–194 Atomic mass units (amu), 44–45 Atomic notation, examples of, 51, 90 Atomic number, definition, 51 Atomic orbitals, definition, 62–63 characteristics of, 62–63 Atomic radius, 57 Atomic symbols, 46–47 Atomic theories, 44–45 Atomic weight, definition, 54 and molar mass, 61 and periodic table, 54, 56 Atoms, component properties, 44–45 ATP See Adenosine 5´-triphosphate Autoclave, pressures in, 195 Autoimmune diseases, 519 Autooxidation, 431 Avobenzone, UV-A blocker, 139 Avogadro, gas law of, 199 Avogadro’s law, for gases, 199, 201 Avogadro’s number, 59 Background radiation, 72–73 Bacteria in recombinant DNA therapy, 526–527 thermophilic, 482, 529 Balanced equations chemical, 153–156, 162–163 and mass relationships, 167–170 Barometer, use of, 192 Base(s) acid/base disorders, 264–266 Brønsted-Lowry definition, 241 buffers and, 261–267 characteristics of, 240 common, 240 conjugate, 302–303 equilibrium and, 243–249 equilibrium constants, 243–246 neutralization of, 257–259 nucleic See Organic bases (amines) pH effects on concentrations, 259–261 pH scale and, 251–254 properties of, 240, 241–242 strength of, 255–256 water as, 242, 250 Base pairing, 509–510, 516, 528 in recombinant DNA, 524 B-cells, 476 Beeswax, characteristics of, 428 Benedict’s reagent reducing sugars and, 384 use of, 347–348 Bent molecular shape, 125–127 Benzene/benzene rings naming of, 288–289 structure and properties of, 288 substitution reaction of, 295 Benzo[a]pyrene, as carcinogen, 289 Benzoyl peroxide, 166 Beta () anomers, definition, 387 Beta glucan, characteristics of, 405 -oxidation spiral, 567, 568–569, 574 Beta particles in nuclear reactions, 68–70 shielding from, 74 -sheet, 470–471 Bextra, effects of, 447 Bicarbonate ion, in buffer system, 263–266 Bile salts, structures and properties of, 443–445 Binary ionic compounds, 97–98 Binary molecules, definition, 103 naming of, 103–104 Binding sites, of proteins, 472, 475 Biochemical compounds, solubility of, 212–215 Biochemistry, 29 measurement in, 32–34 Biofilms, structure of, 315 Bioluminescence, electrons and, 67 1,3-Bisphosphoglycerate, in glycolysis, 542, 553–554 Black Indian salt, 100 Bleach, oxidation/reduction reactions and, 162 Blood clotting, 489, 532 oxygen solubility in, 210 serum solutes, 218–221 Blood plasma, dissolved ions in, 95 Blood pressure, and disorders, 196–197 Blood serum blood serum range, 218 osmosis and, 225–226 pH maintenance of, 263–266 solute concentrations, 218–221 Blood type, oligosaccharides, 395–396 Body Mass Index (BMI), measurement of, 18–19 Body temperature, measurement of, 21–22 Bohr, Niels, atomic model, 62–63 Boiling point(s), definition, 195 of alcohols, 337 of aldehydes, 345–346 of alkanes, 278 of amides, 313 of amines, 310 of carboxylic acids, 298–299 of disulfides, 337–338 of esters, 305 of ethers, 337–338 of fatty acids, 422 of ketones, 345–346 of phenols, 300, 301 of sulfides, 337–338 of thiols, 337–338 of water, 8–9 Bonds See also specific bond covalent, 101–103, 123–129 glycosidic See Glycosidic bonds hydrogen See Hydrogen bonds/ bonding ionic, 97–98, 207 noncovalent interactions, 130–131 peptide, 464–467, 488 and saturation, 287 types, 124 Boyle, Robert, gas law of, 197 Boyle’s law, for gases, 197–198, 200 Brachytherapy, for cancer, 77 BRCA1 and BRCA2 genes, cancer and, 525 Breast cancer, mutation and, 525 Breathing, gas exchange and, 203 Bromides, solubility in water, 207 Bromine (Br), 47 Brønsted-Lowry definition of acids/ bases, 241–242 Brown fat, oxidation of, 566 Buffers, definition, 261 and equilibrium, 261–262 Butanal, physical properties of, 346 Butane conformations of, 284–285 as constitutional isomer, 282–284 uses of, 284 Butanoic acid, properties of, 299 2-Butanol, dehydration, 343 Butanone, physical properties, 346 2-Butene, formation of, 343 2-Buten-1-thiol, 135, 338 Butterfly rash, 519 Cadaverine, properties of, 310 Cadmium, 29–30 Caffeine, 354–355 Calcium, 47 biochemical significance of, 49 dietary reference intake for, 50 Calorie (cal), 10, 12 cAMP (cyclic AMP) structure of, 505 Cancer enzyme therapy in, 489 mutation and, 525 radiation therapy for, 77 Capsaicin, properties of, 300 Caraway, properties of, 376–377 Carbamazepine, 354–355 Carbohydrate(s) acetals in, 353 classification of, 372–373 digestion of, 548–551 functions of, 372 glycogen, 558–560 hemiacetals in, 385–390 monosaccharides and derivatives, 381–383 See also Monosaccharides oligosaccharides, 390–400 oxidation/reduction reactions in, 384–385 problems with digestion, 393–394 stereoisomers of, 379 sweetness of, 397–399 Carbon, 46, 47 alkane-type, 134 biochemical significance of, 49 bonding and shape, 125 isotopes of, 53–54 Carbonates, solubility in water, 207 Carbonation, solubility and, 209 Carbon dioxide (CO2 ) in buffer system, 263–266 carbonic anhydrase reaction, 246–247 in citric acid cycle, 561–562 as dry ice, in fermentation, 555 hemoglobin and, 475 partial pressure and, 203 Carbonic acid (H2 CO3 ) as buffer system, 263–266 in red blood cells, 177–178, 246–247 Carbonic anhydrase, as catalyst, 177– 178, 246–247 Carbonyl group, 136, 345 in oxidative deamination, 571 Carboxylate ions, 302 and fatty acids, 302, 424 naming of, 302 Carboxylate salts formation and use, 303 Carboxyl groups (COOH) in amino acid formation, 460–469 in organic compounds, 136–137, 158 Carboxylic acids from alcohol oxidation, 341–342 from aldehydes, 347 amide formation and, 313–314, 320 ester reactions and, 304–306 naming of, 297 properties of, 299 solubility of, 214 structure and characteristics of, 136–137, 139, 158 as weak acids, 301–304, 319 Carboxylic acid sugars, definition, 382 oxidation of, 384 Carnauba wax, characteristics of, 428 Carvone, properties of, 376–377 Catabolism See also Anabolism, definition, 543 characteristics of, 546–547 energy in, 544–546 fatty acid, 566–569 monosaccharides, 546–547 Catalase, protective function of, 351, 564 Catalysis control of reactions, 482–490 process of, 480 Catalysts, definition, 158 catalytic hydrogenation, 165, 349– 351, 431, 432, 435–436 and equilibrium, 249 and reaction rates, 176 Catalytic hydrogenation, 165, 293, 319 of aldehydes and ketones, 349–351 of triglycerides, 431, 432, 435–436 Catechol, properties of, 300 Cathode ray tube, 45 Cations, definition, 90 in ionic compound formation, 97–98 naming, 91 Celebrex, effects of, 447 Cell membranes lipids in, 437–439 structure of, 437 Cellobiose, structure and properties of, 393 Cellulose, structures and properties of, 401–402 Celsius (°C) scale, 10, 11 conversions, 25, 198 index     I-3 Cerebrosides, structure and functions of, 440 Chain reaction, in fission, 70 Charge(s) atomic, 53 ionic, 90–93 and noncovalent interactions, 130–131 pH and amino acids, 462, 468 of subatomic particles, 44–45 Charles, gas law of, 198 Charles’ law, for gases, 198–199, 200 Chemical change See also Reactions (chemical), definition, 97 rusting example, 97 Chemical composition, definition, and physical change, Chemical equations balancing, 153–156, 162–163 components of, 152–153 Chemical properties, definition, 97 Chemical reactions See Reactions (chemical) Chemistry, definition, Chernobyl plant disaster, 72 Chili pepper, capsaicin properties, 300 Chiral carbon atoms, definition, 374 and cyclic hemiacetals, 387–390 identification of, 374–375 and stereoisomer numbers, 378–380 Chiral objects, definition, 374 Chitin, structure and properties of, 402 Chloramphenicol properties of, 377 solubility and, 215 Chlorides, solubility in water, 207–208 Chlorine, 47 biochemical significance of, 49 Chloroform, shape, 129 Chloroprocaine, 159 Cholesterol, 53 in cell membranes, 447–448 screening tests, 442 structure and properties of, 441–442 Chondroitin 4-sulfate, characteristics of, 404 Chromatin, DNA structure and, 511–512 Chromosomes, DNA structure and, 511–512 Chronic wasting disease, 128 Chylomicrons, function of, 442 Chymotrypsin activation of, 488 in protein digestion, 549 structure and function of, 465–466 Chymotrypsinogen activation of, 488 structure and function of, 465–466 Cinnamaldehyde, 136 Circular metabolic pathways, definition, 542 citric acid cycle as, 560 cis double bonds, effects on properties, 422–423, 431 cis isomers, in organic compounds, 287, 289–290 Citrate, in citric acid cycle, 561–562 Citric acid, 160 Citric acid cycle, definition, 546 amino acids in, 571–573 control of, 562 process of, 560–562 CoA See Coenzyme A Cobalt, biochemical significance of, 49 Cocaine, as local anesthetic, 159 Codons, definition, 518 properties of, 518–520 Coefficients, definition, 152 in balanced equations, 154 Coenzyme A (CoA) in citric acid cycle, 561–562 in metabolism, 544–546 properties of, 481 Coenzymes See also specific coenzyme and catalysis, 480–481 in metabolism, 544–546, 561, 566–569 Cofactors, and catalysis, 480–481 Collagen, properties of, 475 Colloids, definition, 223 properties of, 223 Colon cancer, mutation and, 525 Combined gas law, and ideal gas law, 200–202 Combustion of alkanes, 291 energy changes in, 174 process of, 162–164 Common names for organic compounds, 288 of peptides and proteins, 465–466 Common units, use of, 9–12 Competitive inhibitors/inhibition, definition, 484 characteristics of, 483–485 Complementary base pairings in DNA, 509–510 in DNA replication, 516 in transcription, 517–518 Composite dental fillings, 105 Compounds, definition, 96 ionic, 96–100, 105–106 Computed tomography (CT), 79–80 Concentration(s), definition, 216 of blood serum solutes, 218–221 dilution and, 221–222 equilibrium and, 243–249 molarity and, 218–221 percent and parts per units, 216–217 and reaction rates, 176 titration and, 257–259 Condensed structural formulas, 122–123 Conductivity, physical property of, 54–55, 56 Conformations, results of, 284–285 Conjugate acid(s), definition, 242 of amines, 311 of carboxylic acids and phenols, 302–303 Conjugate base(s) acid strength and, 255–256 of carboxylic acids, 302–303, 319 of phenols, 302–303, 319 pyruvate and pyruvic acid, 551 Conjugated prosthetic groups, and tertiary structure, 473 Constitutional isomers of organic compounds, 282–284 sweetness and, 399 Conversion factors concentration as, 220 use of, 22–25 using moles, 60, 105–107, 167 Conversions concentrations, 219–221 with moles, 60, 105–107, 167 pressure units, 193 temperature, 25, 198 Cooperativity, and allosteric enzymes, 487 Copernicium, 46 Copernicus, Nicolaus, 46 Copper, 47 biochemical significance of, 49 as oxidizing agent, 347 Cortisol, structure and properties of, 443, 444 Cortisone, structure and properties of, 443, 444 Coupled reactions, definition, 542 Covalent bonds, definition, 101 polar, 123–129 Covalent compounds See Molecules Covalent interactions, and tertiary structure, 473 Covalent modification, definition, 487 and enzyme activity, 487–488 in glycogen metabolism, 558–560 COX-1 and COX-2 inhibitors, 447 Creatine kinase (CK), characteristics of, 489 Crenation, 225 Creutzfeldt-Jakob disease, 128 Cryoprotectant, 393 Crystal lattice effect on solubility, 207 sodium chloride as, 98–99 C-terminus, in protein notation, 465–467 Cubic meter (m 3), 10, 11 Curie, Marie, 71 Curie (Ci), 71 Curium, 47 Cyclases, actions of, 505 Cyclic AMP structure of, 505 Cyclic hemiacetals, in sugar formation, 352, 386–390 Cyclic nucleotides, definition, 505 in enzyme reactions, 505 Cycloalkanes, structures and properties of, 285–287 See also Alkanes Cyclooxygenase, and inhibitors, 447 Cysteine (Cys), 135 structure of, 461 Cystic fibrosis, mutation and, 525 Cytidine, structure of, 502 Cytosine (C), structure of, 501 Dally, Clarence, 79 Dalton, John, atomic theory, 44–45 Dalton, unit of mass, 45 Dalton’s law of partial pressure, definition, 204 calculations with, 204 Deamination, oxidative, 571 Decomposition reactions dehydration, 159–160, 358 description of, 157 Dehydration, 28 of alcohols, 343–344, 358 osmosis and, 225 Dehydration reaction, 159–160, 358 Denaturation, definition, 477 fever and, 481 of nucleic acids, 512–513 of proteins, 477 Density, definition, 25 as property, 25–27 Dental fillings, 105 Deoxyadenosine, structure of, 503 Deoxycytidine, structure of, 503 Deoxyguanosine, structure of, 503 Deoxyribonucleic acid (DNA), 32–34 See also Gene expression, control of denaturation of, 512–513 DNA fingerprinting, 529–531 DNA viruses, 521 mitochondrial, 547 recombinant, 525–529 replication, 514–516 structure of, 506–512 Deoxyribonucleosides, definition, 502 structures of, 502–503 Deoxyribonucleotides in DNA replication, 516 formation of, 504 D-2-Deoxyribose anomers of, 388 in biomolecules, 381 in nucleic acids, 500–504 production of, 556 Deoxy sugars, definition, 382 Deoxythymidine, structure of, 503 Dephosphorylation, in enzyme control, 487–488 Deposition, definition, Desaturase enzymes, and fatty acids, 571 Detergents, denaturation and, 477 Deuterium, hydrogen isotope, 52 Dextrorotatory (d) isomers, definition, 376 amino acids, 464 notation for, 376, 380 properties of, 376 Diabetes See also Glucose, blood sugar advances in testing and treatment, 5, 384 and ketone formation, 569 stevia and, 400 Diacylglycerides, in digestion, 549 Diallyl disulfide, 135 Dialysis, diffusion in, 227 Diamond, 46 Diastereomers, definition, 378 and enantiomers, 378–380 Diatomic molecules, 103 Dietary Reference Intakes (DRIs), 48, 50 Diffusion, definition, 225 facilitated, 448 hemodialysis and, 227 across membranes, 448 Digestion, definition, 548 of carbohydrates, 548–551 enzymes of, 224 enzyme therapy and, 489 of fats and oils, 433, 549–550 processes of, 548–551 of proteins, 549–550 Digitalis, properties of, 406 Digital thermometers, 21 Digitoxin, properties of, 406 Digoxin, properties of, 406 Dihydrouracil, 502 Dilution, principles of, 221–222 Dimethyl sulfoxide (DMSO) properties of, 355–356 Dipeptides, definition, 464 characteristics of, 464–465 Diphenhydramine, 316 Dipole-dipole forces/interactions, 130 boiling points and, 337–338, 345 in esters, 305 Dipropylamine, naming of, 308 Disaccharides, characteristics of, 391– 393, 397–399 Disintegrations per second (dps), 71 Dissociation, pH and, 255 Disulfide bridges and protein structure, 472, 473, 474 Disulfides boiling points of, 337–338 naming of, 336 in nature, 135 physical properties of, 336–338 structure and characteristics of, 134, 138 from thiol oxidation, 343 Disulfiram, and ethanol metabolism, 349 DMSO See Dimethyl sulfoxide I-4     index DNA See Deoxyribonucleic acid DNA fingerprinting, 224 process of, 529–531 DNA polymerases heat-resistant, 529 in replication, 515–516 DNA viruses, 521 Docosahexaenoic acid, 426 Dosage units, 71–73 Double bonds in covalent bonding, 101–102 in unsaturated hydrocarbons, 287–290 Double helix in DNA replication, 515–516 in DNA structure, 509–512 Double replacement reactions description of, 157 ester formation, 304–305 hydrolysis, 158–159, 306, 314, 320, 392–393, 401–402, 527, 548–550 Dps (disintegrations per second), 71 Drugs See also specific drug effectiveness of isomers, 377 half-life of, 75 introduced into environment, 354–355 Drug testing, stable isotopes and, 53–54 Dry ice, sublimation and, D sugars, notation, 379 Ductility, physical property of, 54 Dynamometer, 10 Ecamsule, UV-A blocker, 139 Eicosapentaenoic acid, 426 Electromagnetic radiation, definition, 62 Electron dot structures, 66–67, 93, 94, 96, 118 covalent bonding and, 101 Electronegativity, effects on bonding, 123–125 Electrons characteristics of, 44–45 in covalent bonds, 101–103 electron distribution, 62–67 in electron transport chain, 562–565 energy levels and arrangement, 62–67 octet rule and, 93–95 valence, 65–66 Electron transport chain, characteristics of, 546–547, 562–565 Elements, definition, 46 biochemical significance of selected, 49 characteristics of, 46–47 dietary recommendations, 48–49 isotopes of, 52–53 names and symbols of common, 47 periodic table of, 54–57 trace, 48–50 Elongation (protein translation), process of, 520–522 Emulsifying agents, definition, 439 Emulsion(s), definition, 439 Enantiomers, definition, 374 of amino acids, 464 properties of, 375–377 Endonucleases actions of, 516 and recombinant DNA, 526 Endoplasmic reticulum, synthesis of proteins, 517 Endothermic reaction, definition, 174 Energy, definition, in electron transport chain/oxidative phosphorylation, 562–565 free, 174–177, 542–543 and glycolysis, 542–543, 555–556 lipids as sources of, 431, 566–569 measurement of, 12 specific heat and, 28 states of matter and, 5–9 Energy diagrams, 175–177 English units, 10 Enzyme(s) allosteric, 487, 505, 551–554, 561–562 in catalysis process, 177, 384, 480 cofactors and coenzymes, 480–481 cooperativity, 487 covalent modification of, 487–488, 558–560 inhibition, 483–485 Michaelis-Menten, 482–483 naming of, 478 pH and, 263 protective functions, 351, 564 recommended names, 478 restriction, 526 salivary, 224 specificity, 478–479 Enzyme-substrate complex, 480 Epimers, 380 Epinephrine (adrenaline) functions of, 310–311 solubility and, 215 Equilibrium, definition, 243 buffers and, 261–262 pressure and, 247–248 principles of, 243–246 temperature and, 247–248 Equilibrium constant (Keq ), definition, 243 and acid/base strength, 254 derivation of and use, 243–245 for water, 250 Equivalent (Eq), calculations with, 219 Errors, mathematical, 23 Escherichia coli, transcription control, 522–523 Essential amino acids, definition, 572 Essential fatty acids, definition, 571 Esters hydrolysis of, 158, 306, 320 lactones, 315 naming of, 305 phosphate, 500–501 phosphorylation/dephosphorylation, 487–488 properties of, 305 solubility of, 213 structure and characteristics of, 137, 139, 158 synthesis of, 304–307, 319 in waxes, 427–428 Estradiol, structure and properties of, 443, 444 Estrone, properties of, 377 Ethambutol, properties of, 377 Ethanal (acetaldehyde) in fermentation, 555 physical properties of, 346 Ethane properties of, 129, 278 uses of, 284 Ethanoic acid (acetic acid), structure and properties of, 297 Ethanol (ethyl alcohol), 336 combustion of, 291 fermentation of, 555 naming of, 336 oxidation of, 342 solubility of, 212 Ethers boiling points of, 337–338 naming of, 336 in nature, 135 physical properties of, 337–338 preparation of, 339–340 structure and characteristics of, 134, 138, 336–339 Ethyl alcohol, See Ethanol Ethylamine (ethanamine) naming of, 308 properties of, 310 Ethylene as ripening agent, 134 structure of, 287 Ethylene glycol (antifreeze), 348 Ethylmethylamine (N-methylethanamine), properties of, 310 Eugenol, 135 Evaporation, pressure and, 194–195 Exact numbers, definition, 16 Excited state, definition, 62 and electron arrangement, 62 Exfoliation, acids used, 306–307 Exothermic reaction, 174 Experiments, in scientific method, 2–4 Exponential notation See Scientific notation, features and use of Exponents See Scientific notation, features and use of Expression (genes), definition, 522 control of, 522–523 Facilitated diffusion, definition, 447 principles of, 447 Factor label method, for conversions, 22 FAD See Flavin adenine dinucleotide (FAD) FADH2  See Flavin adenine dinucleotide, reduced form (FADH2 ) Fahrenheit (°F) scale, 10, 11 conversions, 25 “Fake fat” (olestra), 436–437 Fat(s), 137 See also Lipid(s) brown, 566 characteristics of, 431 olestra as substitute, 436–437 trans, 435–436 Fatty acid residues in phospholipids, 438–439 in triglycerides, 429–431 Fatty acids, 137, 422 anabolism of, 570–571 catabolism of, 546–547, 566–569 cellular manufacture of, 165 conjugate base form, 424 in digestion, 549–550 omega–3, 426 pH and, 260 in saponification, 431–434 solubility of, 214 structures and properties of, 422–425 Feedback inhibition, 487 Feline version of HIV, 528 Fermentation, alcoholic, process of, 555 Fibrinogen, concentrations, 219–220 Fibrous proteins, 469, 475 Fischer projections, definition, 379 of amino acids, 464 monosaccharides and, 379 Fission, definition, 70 in nuclear reactors, 70 5´-Terminus, definition, 506 Flavin adenine dinucleotide, reduced form (FADH2 ) as coenzyme, 481, 546 Flavin adenine dinucleotide, reduced form (FADH2 ), in metabolism, 544–546, 560–565, 566–569 Flavin adenine dinucleotide (FAD), in metabolism, 544–546, 560–565 Flavr-Savr tomatoes, geneticallymodified food, 527–528 Flea control, 316 Flerovium (Fl), 46 Fluid mosaic model, membrane structure and, 448 Fluorapatite, 109 Fluoride ion, and tooth decay, 108–109 Fluorine, electron dot structure, 66 Fluorine–18, 76–77 2-Fluorobutane structural formulas of, 123 Fomepizole, 348 Food allergies, characteristics of, 458, 490 Foot, 10 Formula weight, definition, 105 of ionic compounds, 105–106 N-Formylmethionine (fMET), in protein synthesis, 519 Foxglove, characteristics of, 370–371, 372, 406 Free energy, definition, 174 and coupled reactions, 542–543, 557 and reaction rates, 174–177 d-Fructofuranose, anomers of, 389 Fructose, 398 characteristics of, 381 glycolysis and, 556 d-Fructose, fruit sugar anomers of, 388, 389 roles of, 381 Fructose 1,6-bisphosphate in gluconeogenesis, 557 in glycolysis, 552–554 Fructose 6-phosphate in gluconeogenesis, 557 in glycolysis, 552–554 l-Fucose, structure of, 382 Functional groups See also specific group or family, definition, 132 Furanoses in anomer naming and depiction, 387, 388 in nucleotides, 500 structures of, 387 Fusion, definition, 70 heat of See Heat of fusion d-Galactopyranose, anomers of, 387 Galactose glycolysis and, 556 relative sweetness of, 398 stereoisomers of, 380 d-Galactose, roles of, 381 Galactosemias, 381, 393 -Galactosidase, 395 -Galactosidase genetic coding for, 522–523 in lactose digestion, 393 Galena, 58 Gamma knife, in cancer therapy, 78 Gamma rays medical use of, 80 in nuclear reactions, 68, 70 shielding from, 74 Gangliosides, structure and functions of, 440 Gas(es), definition, combined and ideal laws, 200–202 exchanges in breathing, 203 mole/volume relationship, 199–200 partial pressure of, 202–204 and pressure, 192–197 index     I-5 pressure/temperature relationship, 198 pressure/volume relationship, 197–198 solubility in water, 209–211 volume/temperature relationship, 198–199 Gas constant (R), definition, 201 Gas laws, 197–202 Gasoline cleaning up after spill, 33 as mixture of alkanes, 284 octane rating, 31–32 Gastric juice, 267 Gay-Lussac, gas law of, 198 Gay-Lussac’s law, for gases, 198, 200 Gene(s), definition, 509 Gene expression, control of, 522–523 Gene insertion, 528 General chemistry, measurement in, 29–30 Genetically modified (GM) foods, tomato example, 527–528 Genetic code, characteristics of, 518–520 Genetic diseases, causes of, 525 Geometric isomers, properties of, 286–287, 289–290 Gestrinone, 449 Glaucoma, epinephrine and, 215 Globular proteins, 469, 476 Gluathione, 141 Glucagon, 560 Gluconeogenesis, definition, 556 process of, 556–558 d-Gluconic acid, structure of, 382 Glucopyranose residues, of polysaccharides, 401 d-Glucosamine, structure of, 382 d-Glucosaminopyranose, anomers of, 388 Glucose See also Glycolysis ATP yield in metabolism, 565 in digestion, 549–550 gluconeogenesis and, 556–558 and glycogen, 558–560 glycolysis and, 551–554 relative sweetness of, 398 testing, Glucose, blood sugar blood serum range, 218 detection in urine, 347, 384 in metabolism, 557–560 solubility of, 213 stereoisomers of, 380 stevia and, 400 d-Glucose as alcohol sugar, 383 anomers of, 386–387 roles of, 381 Glucose oxidase, in diabetes testing, 384 Glucose 6-phosphate in gluconeogenesis, 557 in glycogen metabolism, 558–559 Glucose 1-phosphate, in glycogen metabolism, 558–559 d-Glucuronate, in polysaccharides, 404 d-Glucuronic acid, structure of, 382 Glutamate, and ammonium ion, 571–572 Glutamic acid (Glu) in collagen, 475 structure of, 461, 463 Glutamine (Gln), structure of, 461 Glyceraldehyde, stereoisomers of, 379 Glyceraldehyde 3-phosphate, in glycolysis, 552–554 Glycerol in digestion, 549–550 in lipid metabolism, 566–567 in phospholipid formation, 438–439 in saponification, 431–434 in triglyceride formation, 429–430 Glycerol 3-phosphate, in NADH shuttle, 564 Glycerophospholipids, structures and properties of, 438–439 Glycine (Gly) in collagen, 475 pH and, 462 structure of, 460 Glycocholate, 443, 444 Glycogen metabolism of, 558–560 structure and properties of, 402, 403 Glycogenesis, process of, 558–560 Glycogenolysis, process of, 558–560 Glycogen phosphorylase characteristics of, 487–488 in metabolism, 558–560 Glycogen synthase, in metabolism, 558–560 Glycolic acid, as exfoliant, 306 Glycolipids in cell membranes, 447, 448 structures and properties of, 440–441 Glycolysis, definition, 546 in cancer cells, 554 control of, 554 energy and, 555–556 and gluconeogenesis, 557–558 net reaction for, 554 non-glucose monosaccharides in, 556 pyruvate in, 555 rotenone effects on, 574 steps of process, 551–554 Glycosides, definition, 390 digitalis, 406 N-Glycosides, in nucleotides, 500–501 Glycosidic bonds, definition, 390 in lactose, 523 in oligosaccharides, 390–393 in polysaccharides, 401–404, 549–550 Gold, 47 Gout, role of solubility in, 190–191, 228 Gram (g), 10 Graphite, 46 Gravity, weight and, 11 Gray (Gy), 72 Green fluorescent protein, 528 Grey salt, 100 Ground state, definition, 62 and electron arrangements, 62–65 Groups (periodic table) characteristics of, 56, 57, 58 valence electrons and, 65–66 Growth hormone, 465 Growth hormone-releasing factor, 465 GTC Biotherapeutics, transgenic goats from, 532 Guanine (G), structure of, 501 Guanosine, structure of, 502 Guanosine 5´-diphosphate (GDP), 544 Guanosine 5´-monophosphate (GMP), 544 Guanosine 5´-triphosphate (GTP) in citric acid cycle, 561–562 in metabolism, 544, 546 Guaran, characteristics of, 405 H1N1 virus, 486 H5N1 strain (bird flu), 486 Haber process, 152 Half-life, definition, 74 and radiation exposure, 74–75 Halogenation, 291–293, 319 aromatic, 295–296, 297, 319 Halogens ionization of, 93–94 in periodic table, 56 Hawaiian Sea Salt, 100 HDLs See High density lipoproteins Heat denaturation and, 513 states of matter and, 8–9 Heat of fusion, definition, of water, Heat of vaporization, definition, of water, Heliocentric theory, 46 Helium, 47 ground state electron arrangement for, 64 Helper T-cells, 476 Hemagglutinin, 486 Heme group, 473, 475 Heme prosthetic group, 475 Hemiacetal(s), 352 cyclic, 386–390 formation of, 353–354, 358, 385–386 Hemiketals See Hemiacetal(s) Hemoglobin, 475 Hemolysis, definition, 225 Henderson–Hasselbalch equation, 262 Henry, gas law of, 209 Henry’s law, for gases, 209 Heptane, 31 Heptoses, classification of, 373 Herbicides, half-life of, 75 Heteroatoms, definition, 134 Heterocyclic amines examples, 309 structure and naming of, 309 Heteropolysaccharides, structures and characteristics of, 401, 404–406 Hexanoic acid, properties of, 299 2-Hexanone (methyl butyl ketone), physical properties of, 346 Hexokinase, in glycolysis, 552–554 Hexoses, classification, 373 High density lipoproteins (HDLs) functions of, 442 trans fats and, 435 High fructose corn syrup, sweetness of, 399 Histamine, in allergies, 276, 316 Histidine (His) as essential amino acid, 573 structure of, 461 Histones, supercoiling and, 511–512 HIV, feline version of, 528 Homocystinuria, collagen role in, 476 Homogeneous mixtures, definition, 204 Homopolysaccharides, structures and characteristics of, 401–403 Hormones, definition, 443 ethylene plant example, 134 plant, 134 steroid, 443–444, 445, 449 Human growth hormone (HGH), and recombinant DNA, 527 in athletics, 444 Hyaluronic acid, characteristics of, 404 Hydration reaction, 159–160, 293 Hydrocarbons, definition, 132–133 properties of, 132–133, 138–139, 278–279 reactions of, 291–297, 319 saturation of, 287 shapes of, 133 solubility of, 212 Hydrocodone, 354–355 Hydrogen biochemical significance of, 49 emission spectrum, 62 in fusion, 70 ground state electron arrangement for, 64 isotopes of, 52, 68 Hydrogen-1, fusion of, 70 Hydrogenation reactions, 165 of aldehydes and ketones, 349–351 catalytic, 293, 319 of triglycerides, 431, 432, 435–436 Hydrogen bonds/bonding, definition, 130 in alcohols, 337–338 in amides, 313 in amines, 309–310 in cellulose, 401–402 in monosaccharides, 372 and protein structure, 470–476 Hydrogen peroxide (H2 O2 ) in electron transport chain, 564 Hydrolysis of amides, 314–315, 320, 465 of esters, 306, 320 of peptides, 465–467 of polysaccharides, 401–402, 549–551 reaction of, 158–159 of sugars, 392–393 of triglycerides, 431–434 Hydrometers, specific gravity and, 27 Hydrophilic compounds in cell membranes, 437 and protein structure, 471 solubility of, 213–215, 372 Hydrophobic compounds in cell membranes, 437 solubility of, 213–215, 424, 428 Hydrophobic effect and DNA stability, 510 and protein structure, 471, 472–473, 474, 475, 510 Hydroquinones, 300 Hydroxides, solubility in water, 207–208 Hydroxyapatite, 108–109 3-Hydroxybutyrate, from fatty acid catabolism, 569–570 Hydroxyl groups, 158 Hydroxyproline (Hyp), in collagen, 475 Hydroxysteroid dehydrogenases (HSDHs), 350–351 Hyperbaric medicine, principles of, 210 Hypertension, 196–197 Hypertonic solutions, definition, 225 in medicine, 225–226 Hypothesis/es, definition, in scientific method, 2–4 Hypotonic solutions, definition, 225 in medicine, 225–226 Ibuprofen, properties of, 447 Ideal gases, definition, 201 calculations with, 201 Ideal gas law, and combined gas law, 200–202 Immunotherapy, 476 Inert gases, 56 stability of, 93 Influenza viruses drugs for, 486 infection by, 486 Infrared (IR) energy, thermometers, 22 Inhibition/inhibitors, definition, 484 allosteric enzymes, 487 types and principles, 483–485 Initiation (protein translation), process of, 520–522 Insect wax, characteristics of, 428 Insolubility, definition, 205 I-6     index Insulin, and glycogen metabolism, 560 in recombinant DNA therapy, 527 structure of, 470, 474 International Union of Pure and Applied Chemistry See IUPAC naming rules Intracellular fluid, dissolved ions in, 95 Invert sugar, 397–398, 399 Iodides, solubility in water, 207–208 Iodine, 47 biochemical significance of, 49 dietary reference intake for, 50 as oxidizing agent, 343 reduction of, 161–162 Iodine–131, 76 Ionic bonds, 97–98 See also Salt bridges, definition, 97 and protein structure, 474, 475 solubility and, 207–209 Ionic compounds, 96–100 characteristics of, 96–98 formula weight and molar mass, 105–107 naming of, 99 polyatomic ions in, 98–99 solubility of, 207–209 uses of, 100 Ionic equations neutralization reaction example, 257 precipitation reactions, 208 Ionization acid/base strength and, 254 of water, 250–251 Ionophores, ion transport and, 95, 448 Ions, definition, 90 characteristics and naming of, 90–93 octet rule in formation of, 93–95 Iron, 47 biochemical significance of, 49 dietary reference intake for, 50 Irreversible inhibitors, definition, 484 Isocitrate, in citric acid cycle, 561–562 Isocitrate dehydrogenase, in citric acid cycle, 561–562 Isocitric acid, 160 Isoelectric point (pI), definition, 462 Isoleucine (Ile), 460 as essential amino acid, 573 Isomers constitutional, 282–284, 399 geometric, 286–287, 289–290 stereoisomers, 286, 289 Isooctane, 31 Isopropyl alcohol density and specific gravity of, 26 evaporation and, naming of, 336 structural formulas of, 118 Isotonic solutions, definition, 225 in medicine, 225–226 Isotopes, definition, 52 and drug testing, 53–54 features of, 52–53 radioactive See Radioactive isotopes IUPAC naming rules alcohols, 336–337 aldehydes, 344–345 alkanes, 279–282 alkenes, 288–289 alkyl halides, 340 alkynes, 288–289 amides, 313–314 amines, 307–308 aromatic compounds, 288–289 benzene and benzene rings, 288–289 carboxylic acids, 297 and constitutional isomers, 283 cycloalkanes, 286 disulfides, 336 ethers, 336 ketones, 344–345 sulfides, 336 thiols, 336 Jasmone, 136 Joule (J), 10, 12 Kelvin (K) scale, 10, 12, 198 Keq  See Equilibrium constant Keratin, properties of, 470 Ketals See Acetals Ketoacidosis hazards of, 570 -Ketoglutarate as amino group acceptor, 571–572 in citric acid cycle, 561–562 Ketoheptoses, classification of, 373 Ketone(s) See also Monosaccharides from alcohol oxidation, 341–342 catalytic reduction of, 165 and hemiacetal formation, 352–353, 358 naming of, 344–345 physical properties of, 344–346 reduction of, 349–351, 358 structure and characteristics of, 136, 138 Ketone bodies, in fatty acid catabolism, 569–570 Ketoprofen, 354–355 Ketoses classification of, 372, 373 as reducing sugars, 384 Ketosis, detection of, 570 Kidney dialysis, diffusion in, 227 Kidneys, as buffer system, 264 Kilogram (kg), 10, 11 Kinases creatine kinase (CK), 489 pyruvate, 552–554 Kinetic energy, definition, 7–8 lac operon, properties of, 523 Lactase, in lactose digestion, 393 Lactate anaerobic conditions and, 555 blood serum range, 218 gluconeogenesis and, 556–558 Lactic acid and acidosis, 266 as exfoliant, 306 Lactose active transport of, 438 gene expression and, 522–523 relative sweetness of, 398 structures and properties of, 393 Lactose intolerance, 395 Landis, Floyd, 54 Lanthanide elements, 56 Lauric acid, properties of, 422 Laws, scientific, Lead, 46, 47, 58 Lead acetate, 58 Lead carbonate, 58 Lead chromate, 58 Leaving groups, definition, 339 in substitution reactions, 339–340 Le Châtelier’s principle, examples of, 246–249, 259 Lecithin See Phosphatidylcholine, structure and functions of Length, measurement of, 11 Leucine (Leu) as essential amino acid, 573 structure of, 460, 463 Leucine-enkephalin, structure and function, 466 Leukemia, asparaginase therapy in, 489 Levorotatory (l) isomers, definition, 376 amino acids, 464 notation for, 379 properties of, 376 Lewis, and electron dot structures, 66 Lewis method, 101 Lewis structure, 118 drawing, 119–123 Lidocaine, 159 Ligases, and DNA replication, 516 Lightning, nitrogen fixation and, 152 “Like dissolves like,” solubility rule, 205, 212, 338–339, 345 Limiting reactant, 171–172 Linear metabolic pathways, definition, 542 glycolysis as, 542–543 Linear molecular shape, 127 Linoleic acid enzyme activity and, 571 properties of, 422 in triglycerides, 429 Linolenic acid, 426 enzyme activity and, 571 properties of, 422 Lipase enzymes, 549–550 Lipid(s), definition, 422 in cell membranes, 447–449 characteristics of, 421 digestion of, 549 fatty acids See Fatty acids glycolipids, 440–441 metabolism of, 566–571 phospholipids, 437–439 steroids, 441–445, 449 triglycerides, 429–437 waxes, 427–428 Lipid metabolism fatty acid catabolism, 566–569 and ketone bodies, 569–570 Lipogenesis, process of, 570 Lipoproteins, as transport vehicles, 442, 549 Liquid(s), definition, lipids as, 423, 431 Liter (L), 10, 11 Lithium electron dot structure, 66 ground state electron arrangement for, 64 Liver failure, acute, 141 Livermorium (Lv), 46 Logarithms, use of, 251 London forces boiling points and, 298, 337, 338, 345, 422 characteristics of, 130–131 in esters, 305 fatty acids and, 422–423 Lowry, definition of acids/bases, 241 l sugars examples, 382 notation, 379 Lufenuron, amide structure in, 316 Lupus (systemic lupus erythematosus), 519 Luster, physical property of, 54–55 Lysine (Lys) as essential amino acid, 573 structure of, 461, 463 Macrophages, 476 Macular degeneration, 524 Mad cow disease, 128 Magnesium, 47 biochemical significance of, 49 Magnetic Resonance Imaging (MRI), 79–80 Major bases (nucleotides) in nucleic acids, 501–503 Malate, in NADH shuttle, 564 Malleability, physical property of, 54–55 Maltase, in carbohydrate digestion, 392, 401 Maltose relative sweetness of, 398 structures and properties of, 391–393 Manganese biochemical significance of, 49 dietary reference intake for, 50 Mannose, glycolysis and, 556 Manometer, use of, 194 Markovnikov, Victor, 294 Markovnikov’s rule, 293–294 Mars Climate Orbiter, 23 Mass density and, 25–27 measurement of, 10–11 molar, 61, 106–107 specific heat and, 28 of subatomic particles, 45 weight vs., 10–11 Mass number, definition, 51 Mass relationships, in chemical reactions, 167–170 Matrix of mitochondria, 547 Matter, definition, characteristics of, Measurement(s) accuracy and precision, 15–16 conversion of, 22–25 in different subdisciplines of chemistry, 29–34 significant figures in, 15–21 units of, 9–12 Medical imaging, 76–80 Medicine, radioisotopes in, 71–80 controlling exposure to radiation, 73–75 CT and MRI imaging, 79–80 diagnosis and therapy, 75–78 dosage units, 71–73 Melamine, food contamination with, 309 Melting point(s) fatty acids, 422–423 monosaccharides, 372 triglycerides, 431 Membrane(s), 437–439, 447–449 Mendeleev, Dmitri, 56 Menthol, 135 Mercaptan compounds, naming of, 336 Mercury (element), 47 in dental fillings, 105 in seafood, 426 in thermometers, 21 Messenger RNA (mRNA) characteristics of, 518 in protein synthesis, 518–520 Metabolic pathways, definition, 542 circular, 542, 560 linear, 542 spiral, 542, 567, 568–569, 570, 574 Metabolism, definition, 543 amino acid, 571–573 anabolism, 543–546 ATP in, 544–546 catabolism, 543–546 citric acid cycle, 560–562 digestion, 548–551 fatty acid, 566–569 gluconeogenesis, 556–558 of glycogen, 558–560 index     I-7 glycolysis, 550–556 important compounds in, 542–546 Metalloids (semimetals), properties of, 54–57 Metals ionic bonding of, 97–98 ionization in, 94 ions as enzyme inhibitors, 485 in periodic table, 54–57 properties of, 54–57 meta (m) position, in naming, 288, 299 Meter (m), 10, 11 Methanal (formaldehyde), physical properties of, 346 Methane combustion of, 162–164, 291 properties of, 132, 278 uses of, 284 Methanoic acid (formic acid), structure and properties of, 297 Methanol (methyl alcohol), 337 Methionine (Met), 135 as essential amino acid, 573 in ethylene, 134 in genetic code, 519 structure of, 460 3-Methy-1-butanethiol, 135 Methylamine (methanamine) naming of, 308 pH and, 260–261 properties of, 310, 311 Methylammonium ion, in acid-base reaction, 311 Methylbenzene (toluene), structure and naming of, 288–289 3-Methyl-1-butanethiol, 338 2-methylbutanoic acid, naming of, 302 Methyl chloride, in alcohol preparation, 339–340 7-Methylguanine, 502 Methylsulfonylmethane (MSM), properties of, 355–356 Metric prefixes, 14–15 Metric system metric prefixes, 14–15 units used, 10–12 Micelles, behavior in solution, 214 Michaelis constant, definition, 482 Michaelis-Menten enzymes, 482–483 Minor bases (nucleotides), definition, 502 Mitochondria characteristics of, 547, 548 citric acid cycle in, 555, 560 electron transport chain and, 562–565 origin of, 547 Mixtures, definition, 204 Molarity (M) calculations with, 218–221 definition, 218 Molar mass, definition, 61 and weights, 106–107 Mole (unit), 59–61, definition, 59 conversions with, 60, 105–107 and mass, 61 volume and, 199–200 Molecular formula, definition, 103 Molecular weight, definition, 107 Molecules, definition, 103 molecular weight, 107 naming of, 103–104 shapes, 126–128 Monoacylglycerides, in digestion, 549–550 Monoatomic ions, definition, 90 Monoclonal antibodies, 476 Monosaccharides catabolism of, 546–547 classification of, 372–373 cyclic form of, 386–390 derivatives of, 381–383 in glycolipid formation, 440 glycolysis of, 556 importance of common, 381–383 mutarotation of, 388–390 in nucleotides, 500 properties of, 372–373 reactions of, 384–386 stereoisomers in, 379–380 Monounsaturated fatty acids, properties of, 422–423 Mucins, salivary, 224 Muscalure, 132 alkene structure, 288 Muscarine iodide, structure of, 312 Mutarotation, of monosaccharides, 388–390 Mutation, definition, 524 and gene expression, 524–525 viral, 521 Myelin, phospholipids in, 439, 440 Myocardial infarction, proteins and, 489 Myoglobin, in reversible reaction, 249 MyPlate (USDA), 48 Myristic acid, properties of, 422 NAD 1 See Nicotinamide adenine dinucleotide NADH See Nicotinamide adenine dinucleotide, reduced form NADPH See Nicotinamide adenine dinucleotide phosphate, reduced form Nandrolone laurate, properties of, 445 Naphthalene, 132, 288–289 NAPQI (N-Acetyl-p-benzoquinone imine), 141 Native molecules effect on enzyme activity, 481 in protein structure, 471 Negative effectors actions of, 487 in citric acid cycle, 561–562 in glycolysis, 552–554 Neon (Ne), 47 Net ionic equations, 208 Neuraminidase, 486 Neutralization, definition, 257 Neutral solutions, definition, 251–254 Neutrons, characteristics of, 44–45 Newton, Isaac, observation and, Nicotinamide adenine dinucleotide (NAD +) in alcohol oxidation, 342, 349 in citric acid cycle, 561–562 in lipid metabolism, 566–569 in metabolism, 544–546 Nicotinamide adenine dinucleotide, reduced form (NADH) in citric acid cycle, 561–562 as coenzyme, 481, 546 in glycolysis, 551–554 in lipid metabolism, 566–569 in metabolism, 544–546, 555 shuttles, 564 in steroid synthesis, 350–351 Nicotinamide adenine dinucleotide phosphate, reduced form (NADPH), in metabolism, 544–546, 570–571 Nicotine, 354–355 structure of, 309 Nitrates, solubility in water, 207–208 Nitric oxide, roles in body, 108 Nitrogen, 47 biochemical significance of, 49 excretion of, 572 Nitrogen fixation, 152 Noble gases See Inert gases Nonbonding electrons, 101 Noncompetitive inhibitors/inhibition characteristics, definition, 483–485 Noncovalent interactions See also specific force, definition, 130 effects on properties, 130–131 and protein structure, 472–473 Nonmetals covalent bonding of, 101 ionization in, 93–94 properties of, 54–57 Nonoses, classification of, 373 Nonpolar amino acids, characteristics of, 460, 463 Nonpolar molecules characteristics of, 127–128 diffusion across membranes, 448 Nonspontaneous reactions, definition, 174 and coupled reactions, 542–543 reaction rates and, 174–177 Nonsteroidal anti-inflammatory drugs (NSAIDs), properties of, 447 Normal hydrocarbon structure, 278 Novocain, hydrolysis of, 159 NSAIDs (nonsteroidal antiinflammatory drugs), 447 N-terminus, in protein notation, 465–467 Nuclear change, 68 Nuclear equations, 68–71 balancing of, 68–71 Nuclear radiation, definition, 68 exposure and control of, 73–74 health effects of short-term exposure to, 72–73 types of, 68–71 Nucleic acid(s) See also Deoxyribonucleic acid (DNA); Ribonucleic acid (RNA) denaturation of, 512–513 and genetic information flow, 514–515 nucleotides in, 500–504 pH and, 506 Nucleophiles, definition, 339 in substitution reactions, 339–341, 357 Nucleophilic substitution reactions process of, 339–341, 357 product prediction, 340 Nucleoside diphosphates, 505 Nucleosides, definition, 502 structures of, 502–503 Nucleoside triphosphates importance in metabolism, 544–546 structure and properties of, 505 Nucleosomes, DNA structure and, 511–512 Nucleotides, 32, definition, 500 components of, 500–504 cyclic, 505 Nucleus (atomic), definition, 44 Nutrasweet, artificial sweetener, 399 Nutrition, dietary recommendations and, 48–49 Nutrition Facts label, 49–50 Obesity in the United States, 18 Observations, Octane rating, 31–32 Octanoic acid ATP generation from, 568 solubility of, 213 Octet rule, in ion formation, 93–95 Octoses, classification of, 373 Octyl methoxycinnamate, UV-B blocker, 139 Oils, 137 See also Lipid(s) digestion of, 549–550 properties of, 429–431 Oleic acid pH and, 260 properties of, 422 solubility of, 214 in triglycerides, 429 Olestra, health issues, 436–437 Oligonucleotides, definition, 506 Oligopeptides, definition, 464 characteristics of, 464–466 Oligosaccharides, definition, 390 disaccharides, 390–393, 397–399 functions of, 390–396 in ganglioside formation, 440 in plants, 393–394 Omega-3 fatty acids in diet, 426 sources of, 429 Omega-6 fatty acids, 426 Operons, definition, 523 Orbitals, electron, 62–63 Organic bases (amines) in DNA fingerprinting, 529–531 in DNA replication, 516 in nucleotides, 501–502 in transcription, 517–519 Organic chemistry, 29 measurement in, 31–32 Organic compounds conformations in, 284–285 constitutional isomers, 282–284 solubility of, 212–215 and structural formulas, 278–280 Origin (DNA replication), definition, 515 formation of, 515–516 ortho (o) position, in naming, 288, 299 Osmosis, definition, 225 principles and effects of, 225–227 Osmotic pressure, definition, 225 effects on cells, 225 Ovarian cancer, mutation and, 525 Oxalic acid, 348 Oxaloacetate in citric acid cycle, 561–562 in electron transport chain, 564 in gluconeogenesis, 557–558 Oxandrolone, properties of, 445 Oxidation/oxidation reactions, definition, 161–167 of alcohols, 341–342, 358 of aldehydes, 347–348, 358 antisepsis and, 166 of brown fat, 566 in citric acid cycle, 561–562 combustion, 162–164 of fatty acids, 546–547, 566–569 reduction by-products, 351 rules for identifying, 163 of thiols, 343, 358 of triglycerides, 431, 434, 566 Oxidative deamination, definition, 571 Oxidative phosphorylation and catabolism, 546–547 process of, 562–565 Oxidizing agent(s), definition, 161 Benedict’s reagent, 347–348, 384 iodine, 343 potassium dichromate, 341, 347 Oxygen, 47 biochemical significance of, 49 in combustion, 162–164 hemoglobin and, 475 hyperbaric medicine and, 210 Oxygen gas, partial pressure and, 203 Oxytocin, structure and function of, 466 Palmitate ion, structure of, 302 I-8     index Palmitic acid properties of, 422 structure of, 302 in triglycerides, 429 Palmitoleic acid, properties of, 422 Papain, as catalyst, 480 Parallel sheets, in protein structure, 470 para (p) position, in naming, 288, 299 Parent chain, in IUPAC naming rules, 279–280 Partial charges, noncovalent interactions due to temporary, 130–131 Partial pressure, definition, 204 in gas mixtures, 202–204 Parts per thousand/million/billion, calculations of, 216–217 PCR See Polymerase chain reaction Peanut allergy, 458, 490 Pectin, hydrolysis of, 527 Pentanoic acid, properties of, 299 2-Pentanone (methyl propyl ketone), 346 Pentose phosphate pathway, definition, 556 Pentoses, classification of, 372, 373 Pepsin in digestion, 549 pH and, 481 Peptide bonds, definition, 464 in digestion, 549 in peptide and protein formation, 464–467 in zymogen activation, 488 Peptides, definition, 464 characteristics of, 464–467 naming of, 465–466 pH and, 468–469 solubility of, 468 Percent yield, calculation of, 173 Periodic table of the elements, definition, 54–58 organization, 54–57 table, 55 valence electrons and, 65–66 Periods (periodic table) characteristics of, 56–57 valence electrons and, 65–66 Permanent charges, noncovalent interactions due to, 130 Permeability, of membranes, 448 Peroxidase, as cofactor, 481 Pesticides, half-life of, 75 PET (positron emission tomography), 76–77 Petroleum, alkane components of, 284 Phagocytosis, 351 pH (and pH scale), definition, 251 of blood serum, 263–266 and buffers, 261–267 calculations with, 251–254 common solutions and, 251 and conjugate concentrations, 259–261 denaturation and, 477 effect on amino acid structure, 462 peptides/proteins and, 468–469 Phases of matter See States of matter Phenanthrene, structure and properties of, 289 Phenol(s), definition, 134 naming and properties of, 299–301 in nature, 135 structure and characteristics of, 138 as weak organic acids, 302–303, 319 Phenoxide ion, naming of, 302 Phenoxide salts, solubility of, 303 Phenylalanine (Phe), 151 in aspartame, 151, 178–179 as essential amino acid, 573 structure of, 460 Phenylalanine hydroxylase, 178–179 Phenylephrine, 311 Phenylketonuria (PKU), 150, 151, 178–179 pH indicators, 252 plants as, 257 pH optimum, enzyme activity and, 481 Phosphate ester bonds, in phospholipids, 438 Phosphate esters, in nucleotides, 500–501 Phosphate ion in buffer system, 264 in phospholipids, 437 Phosphates solubility in water, 207 Phosphatidylcholine (lecithin), structure and functions of, 438, 439 Phosphatidylethanolamine (cephalin), structure and functions of, 438, 439 Phosphatidylserine, structure and functions of, 438, 439 Phosphodiester bonds, in polynucleotides, 506 Phosphoenolpyruvate in gluconeogenesis, 557–558 in glycolysis, 553–554 Phosphoester bonds in nucleic acids, 503, 505 Phosphofructokinase, in glycolysis, 552–554 2-Phosphoglycerate, in glycolysis, 553–554 3-Phosphoglycerate, in glycolysis, 542–543, 553–554 Phospholipids in cell membranes, 447–448 structures and properties of, 438–439 transport to cells, 442 Phosphorus, 47 biochemical significance of, 49 dietary reference intake for, 50 Phosphorylation, in enzyme control, 487–488 Photosynthesis, 54 Physical changes, definition, characteristics of, 6–7 Physical properties, definition, pKa     pKa = -logKa Plane-polarized light, enantiomers and, 376 Plant hormones, 134 Plants, as pH indicators, 257 Plasmids and recombinant DNA, 526–527 supercoiling in, 511–512 Platinum, as catalyst, 165, 349, 431 Plutonium, 47 Plutonium–239 half-life of, 74 Polar-acidic amino acids, characteristics of, 461, 463, 473 Polar-basic amino acids, characteristics of, 461, 463, 471 Polar covalent bonds, definition, 124 in amines, 309–310 and polarity, 127–128 and shape, 126–128 Polarity, of molecules, 127–128 Polar molecules, characteristics of, 127–128 Polar-neutral amino acids, characteristics of, 461, 463 Polyatomic ions, definition, 92 common examples, 92–93 in ionic compounds, 98–99 structural formulas of, 121–123 Polycyclic aromatic hydrocarbons (PAHs), structures of, 288–289 Polymerase chain reaction (PCR) in DNA fingerprinting, 529–531 enzymes in, 482 Polynucleotides, definition, 506 structures and properties of, 506–509 Polypeptide backbone, in protein structure, 470 Polypeptides See also Protein(s), definition, 464 backbone, 470 Polysaccharides, definition, 372, 401 heteropolysaccharides, 404–406 homopolysaccharides, 401–403 Polyunsaturated fatty acids, properties of, 422–423 Positive effectors actions of, 487 in citric acid cycle, 561–562 in glycolysis, 552–554 Positron emission tomography (PET), positrons and, 76–77 Positrons, in nuclear reactions, 68, 69 Post-transcriptional modifications, of RNA, 518, 519 Post-translational modifications, of proteins, 522 Potassium, 47 biochemical significance of, 49 Potassium dichromate, oxidation and, 341, 347 Potassium sorbate, 303 Potential energy, definition, 7–8 Pound (lb), 10, 11 Precipitates, definition, 205 Precipitation reactions, solubility and, 207–209 Precision, definition, 16 measurement and, 16 Pressure, 192 atmospheric, 192–194 blood, 196–197 equilibrium and, 247–248 Le Châtelier’s principle and, 247–248 osmotic, 225–227 solubility and, 209–210 temperature and, 198 vapor, 194–196 volume and, 197–198 Primary (1°) alcohol classification of, 337 formation of, 349–350 oxidation of, 341–342 Primary (1°) amine, definition, 307 Primary structure (DNA), 509 as blueprint for life, 514 Primary structure (proteins), definition, 469 characteristics of, 469–470 Prions and prion diseases, 128 Procaine, hydrolysis of, 159 Prodrugs, 215 Product recalls, cadmium-related, 30 Products (chemical reactions), definition, 152 in balanced equations, 154 and equilibrium, 243–246 yield and, 171–173 Progesterone, 136 structure and properties of, 443–444 in testosterone synthesis, 53 Proline (Pro) in collagen, 475 structure of, 460 Promoter sites, definition, 517 operons and, 523 Proofreading (DNA replication), 516, 525 Propanal, physical properties of, 346 Propane combustion of, 291 properties of, 278 structural formulas of, 123 uses of, 284 Propanoate ion, 302 Propanoic acid, properties of, 299, 302 2-propanol See Isopropyl alcohol Propanone (dimethyl ketone, acetone) from fatty acid catabolism, 569–570 physical properties of, 346 Propranolol, properties of, 377 Propylamine (1-Propanamine), 310 Prostaglandins aspirin and, 484 Prostate cancer mutation and, 525 treatments for, 77 Prosthetic group heme, 475 tertiary structure and, 473 Protease enzymes, 549–550 Protein(s) See also Amino acids; Gene expression, control of; Transcription; Translation (protein synthesis), definition, 464 in allergies, 458, 490 in cell membranes, 447–448 denaturation of, 477 digestion of, 549–550 green fluorescent, 528 in medicine, 489, 498, 532 naming of, 464–465 pH and, 263–264, 468–469 post-translational modification of, 522 primary structure of, 469–470 prions, 128 quaternary structure of, 473–474 secondary structure of, 470–471 structure of, 469–476 synthesis (translation) of, 520–522 tertiary structure of, 471–473 Protium, hydrogen isotope, 52 Protons and atomic number, 51 characteristics of, 44–45 Pseudoephedrine solubility of, 312 structure and functions of, 311 Pure substances, definition, 96 PureVia, as sugar substitute, 400, 401 Purines in gout, 228 in nucleic acids, 501–503 structure of, 309 Putrescine, properties of, 310 Pyramidal molecular shape, 125–126 Pyranoses in anomer naming, 387 structures of, 387 Pyridine, structure of, 309 Pyrimidines in nucleic acids, 501–503 structure of, 309 Pyrophosphate (PPi ), in fatty acid catabolism, 568 Pyruvate in alcoholic fermentation, 555 in glycolysis, 546–547, 555 Pyruvate dehydrogenase complex, in glycolysis, 555 Pyruvate kinase, in glycolysis, 552–554 Pyruvic acid in glycolysis, 551 Quality factor (QF), 71–72 Quantum mechanics, and electron levels, 62–63 Quart, 10, 11 Quaternary (4°) ammonium ions, definition, 307 index     I-9 Quaternary structure (proteins), definition, 473 characteristics of, 473–474 Quorum sensing, 315 Racemic mixtures, properties of, 376 Rad (radiation absorbed dose), 71 Radiation units, 71–73 Radioactive decay, 70 Radioactive isotopes (radioisotopes), definition, 68–71 in consumer products, 79 in diagnosis and therapy, 75–78 half-life of, 74–75 radiation emission by, 68–71 Radon, dangers of, 73 Radon-222, half-life of, 74 Raffinose, 394, 395 Rash, butterfly, 519 Rates, reaction See Reaction rates Reactants, definition, 152 in balanced equations, 153–154, 167–170 and equilibrium, 243–246 limiting, 171–172 Reaction energy diagrams, 175–177 Reaction rates, definition, 175 factors in, 176, 480 Reactions (chemical) dehydration, 159–160, 343–344, 358 hydration, 159–160 hydrogenation, 165, 349–351, 431, 432, 435–436 hydrolysis, 158–159, 306, 314–315, 320, 392–393, 401–402, 431– 434, 465–467, 527, 549–551 nucleophilic, 339–341, 357 oxidation/reduction, 161–167, 349–351, 358, 384–385 types, 156–158, 291 yield calculation, 171–173 Rebaudioside A, 398, 400 as sugar replacement, 400, 401 Recombinant DNA, definition, 525 process and applications, 525–529, 532 Recommended Dietary Allowances (RDAs), 48 Recommended names, for enzymes, 478 Rectal temperature, 21 Red blood cells carbonic acid and, 177–178, 247 effects of osmosis, 225–226 phospholipids in membranes, 438–439 Reducing agents, definition, 161 disulfide bonds and, 473 Reducing sugars characteristics of, 384 disaccharide examples, 391–393 Reduction/reduction reactions See also catalytic hydrogenation, definition, 161 of monosaccharides, 384 rules for identifying, 163 Refractometers, specific gravity and, 27 Relative specificity, definition, 478 Relenza, 486 Rem, 71 Renaturation, of DNA, 513 Repair, in DNA replication, 516, 525 Replication, definition, 514 DNA, 514–516 semiconservative, 515 Replication fork, definition, 516 Representative elements in periodic table, 56 valence electrons and, 65 Residues, definition, 304 Resorcinol, properties of, 300 Respiration, role in buffer systems, 264–266 Restriction enzymes, and recombinant DNA, 526 Retroviruses, replication and, 521 Reverse transcriptase, and viral DNA, 521 Reverse transcription, 514, 521 Reversible inhibitors, definition, 484 Reversible reactions equilibrium and, 243–248 Le Châtelier’s principle in, 246–249 l-Rhamnose, structure of, 382 Ribitol, structure and functions, 382, 383 Ribonucleic acid (RNA) as enzyme, 478 partial structure of, 506, 508 transcription of, 517–520 types of, 518 Ribonucleosides, definition, 502 structures of, 502–503 Ribonucleotides, formation of, 504 d-Ribose, 383 anomers of, 388 in biomolecules, 381 in nucleic acids, 500–504 production of, 556 Ribosomal RNAs characteristics of, 518 in protein synthesis, 518 Ribosomes, definition, 518 in protein synthesis, 518–520 Ripening, 134 Rituximab, 476 RNA See Ribonucleic acid RNA interference (RNAi), 524 RNA polymerase, in transcription, 517 RNA splicing, 519 RNA viruses, 521 Roentgen, Wilhelm, Rotenone, electron transport chain inhibitor, 540, 574 Rounding numbers, 19–20 Rubbing alcohol See Isopropyl alcohol Saccharin, structure and properties of, 398, 399 Saliva, components and functions of, 224 Salivary amylase, in digestion, 549 Salt, 100 See also Sodium chloride Salt bridges, definition, 263 and protein structure, 473 Salts amine, 311–312 of hydrolysis, 306 of weak organic acids, 303 Saponification, process of, 431–434 Saturated fatty acids, properties of, 422–423 Saturated hydrocarbons, definition, 287 Saturated solutions, definition, 216 Saturated triglycerides, characteristics of, 429–431 Schrödinger, Erwin, and quantum mechanics, 62 Scientific laws, definition, Scientific method, definition, steps of, 2–3 Scientific notation, features and use of, 13–14 Scrapie, 128 Scurvy, collagen role in, 476 Sea salt, 100 Secondary (2°) alcohol classification of, 337 formation of, 349–350 oxidation of, 341–342 Secondary (2°) amines, definition, 307 Secondary structure (DNA), characteristics of, 509–510 Secondary structure (proteins), definition, 470 characteristics of, 470–471 Seivert (Sv), 72 Selenium biochemical significance of, 49 dietary reference intake for, 50 Semiconservative replication, of DNA, 515 Semimetals (metalloids), properties of, 54–57 Semipermeable membranes, diffusion and, 225–226 Serine (Ser), structure of, 461, 463 Sex hormones, structures and properties of, 443–444 Shielding, radiation and, 73–74 Short tandem repeats (STRs), in DNA fingerprinting, 529–531 Sickle cell anemia, mutation and, 525 Significant figures, 15–22 calculations with, 19–21 characteristics of, 16–19 logarithms and, 253–254 Silicon, properties of, 55–56 Silk, properties of, 470 Silver, properties of, 56 Silver (Ag), 47 Silver nitrate, aqueous, 205, 207 Simple proteins, 473 Single bonds, in covalent bonding, 101–102 Single replacement reactions, description of, 157 Single-strand binding proteins (SSBs), in DNA replication, 515, 516 Sitosterol, 53 SI units prefixes, 14–15 for radiation, 72 use of, 10 Skeletal structural formulas, 122–123 for cyclic compounds, 122–123 Skinfold measurement, 18, 19 Skunk spray, 338 snRNPs, 519 Soaps denaturation and, 477 saponification, 431–434 solubility of, 214 Sodium, 47 biochemical significance of, 49 dietary reference intake for, 50 Sodium chloride, 96 crystal lattice structure of, 97–98 iodized, 100 Sodium cyclamate, structure and properties of, 398, 399 Sodium hydroxide, in saponification, 433 Sodium ion (Na 1), blood serum range, 218 Solid(s), definition, lipids as, 422, 431 Solubility, definition, 205 of alcohols, 337–339 of aldehydes, 346 of amines, 310 of amino acids, 213 of carboxylic acids, 300, 303 of disulfides, 337–338 of esters, 213 of ethers, 337–338 of fatty acids, 424 of gases in water, 209–211 of ionic compounds, 207–209 of ketones, 346, 569 of peptides, 468 of phenols, 300, 301 pressure and, 209–210 of salts, 311–312 of soaps, 214 of sulfides, 337–338 and temperature, 205 of thiols, 337–338 water and, 212–215 of waxes, 428 Solutes See also Concentration(s), definition, 204 characteristics of, 204–206 in diffusion and osmosis, 225–226 Solutions, definition, 204 characteristics of, 204–206 saturation of, 216 Solvents See also Concentration(s), definition, 204 characteristics of, 204–206 in diffusion and osmosis, 225–226 Somatostatin, function of, 465 Sorbitol relative sweetness of, 398 structure and functions of, 382, 383, 384, 399 Spearmint, properties of, 377 Specific gravity, definition, 27 of gasoline, 32, 33 Specific heat, definition, 28 Specificity (enzyme), degrees, 478–479 Spectator ions, definition, 208 in ionic equations, 208 Sphingolipids, structures and properties of, 439–440 Sphingosine, structure and function of, 439–440 Sphygmomanometer, use of, 194, 196 Spiral metabolic pathways, definition, 542 lipogenesis, 570 -oxidation spiral, 567, 568–569, 574 Splenda, artificial sweetener, 399 Spoilage, hydrogenation and, 431 Spontaneous reactions, definition, 174 and coupled reactions, 542–543 reaction rates and, 174–177 Stachyose, structure and properties of, 394, 395 Standard temperature and pressure (STP), 193, 194 Starch digestion of, 549–550 structures and properties of, 401, 403 States of matter and energy, 6–8 in chemical equations, 153 Statue of Liberty, patina on, 99 Stearic acid, properties of, 422 Stereoisomers, definition, 286, 374–381 of alkenes, 289–290 of amino acids, 463–464 of cycloalkanes, 286 diastereomers, 378–380 enantiomers, 374–380 and enzyme specificity, 478 maximum number formula, 378 Stereospecificity, definition, 478 Steroid hormones health issues, 445 structures and properties of, 443– 444, 449 Steroids and bile salts, 443–445 steroid hormones, 443–444, 445, 449 structures and properties of, 441– 442, 445, 449 Stevia, as sugar substitute, 400–401 Stevioside, as sugar substitute, 400 Structural formulas, 118–123 See also Electron dot structures condensed, 122–123 Lewis structures, 119–123 I-10     index Structural formulas, (cont.) molecular shape and, 126–128 skeletal, 122–123 Subatomic particles, characteristics of, 44–45 Sublimation, definition, Substituents (atoms), in IUPAC naming rules, 279 Substitution reaction, 291 aromatic, 295–297 nucleophilic, 339–341, 357 Substrates, definition, 478 in competition and inhibition, 483–485 and reaction rates, 482 and specificity, 478 Succinyl-CoA, in citric acid cycle, 561–562 Sucralose, structure and properties of, 398, 399 Sucrase, in digestion, 549 Sucrose (table sugar) and relative sweetness, 397–399 structures and properties of, 393– 394, 398 Sugar(s) anomers of, 386–390 in glycolipids, 440 monosaccharide derivatives, 381–383 reactions of, 384–385 sweetness of, 397–399 Sugar-phosphate backbone, of nucleic acids, 506–508, 510, 526 Sulfanilamide, inhibitor effect of, 484 Sulfates, solubility in water, 207 Sulfides boiling points of, 337–338 naming of, 336 in nature, 135 physical properties of, 337–338 preparation of, 339–340 structure and characteristics of, 134, 138 Sulfur See Disulfides; Sulfides; Thiols Sun, fusion reactions in, 70 Sunette, artificial sweetener, 399 Sunscreens, aromatic compounds in, 139 Supercoiling, of DNA, 511–512 Superoxide dismutase, protective function of, 351, 564 Superoxide ion, 564 Surface water, contaminated, 80 Suspensions, definition, 223 properties of, 223 Sweeteners, natural and artificial, 397–400 Sweet’ N Low, artificial sweetener, 399 Synthesis reactions description of, 157 hydration, 159 hydrogenation, 165, 349–351, 431, 432, 435–436 Systemic lupus erythematosus (lupus), 519 Tamiflu, 486 Taurocholate, structure and properties of, 443, 444 Temperature(s) body, 21–22 conversions of, 25, 198 denaturation and, 477, 513 density and, 26 enzyme activity and, 481–482 equilibrium and, 247–248 fatty acids and, 422–423 Le Châtelier’s principle and, 247–248 measurement of, 11–12, 21–22 pressure and, 198 and reaction rates, 176 solubility and, 205 specific heat and, 28 volume and, 198–199 Temperature optimum (enzyme), enzyme activity and, 481, 482 Template strand, definition, 517 Temporal artery thermometers, 21–22 Termination (protein translation), process of, 520–522 Termination sequence, in transcription, 517 Tertiary (3°) alcohol, classification of, 337 Tertiary (3°) amines, definition, 307 Tertiary structure (DNA), characteristics of, 511–512 Tertiary structure (proteins), definition, 471 bond interactions and, 472–473 characteristics of, 471–472 Testosterone, 136 blood serum range, 218 structure and properties of, 443, 444, 445 synthetic, 53–54 Tetrahedral molecular shape, 125–128 Tetrahydrogestrinone (THG), 420 synthesis of, 449 Tetrapeptides, definition, 464 characteristics of, 464 Tetroses, classification of, 372, 373 Theoretical yield, definition, 172 calculation of, 172–173 Theories, in scientific method, 2–3 THG (tetrahydrogestrinone), 449 Thiols boiling points of, 337–338 in enzymes, 485 name origin of, 135 in nature, 135 oxidation of, 343, 358 physical properties of, 337–338 preparation of, 339–340 structure and characteristics of, 134, 138 4-Thiouracil, 502 3´-Terminus, definition, 506 Threonine (Thr) as essential amino acid, 573 structure of, 461 Thymine (T), structure of, 309, 501 Thyroid scan, 76, 77 Thyrotropin, function of, 465 Thyrotropin-releasing factor, 465 Tin, 47 Tincture of iodine, 166 Titin, function of, 465 Titration, technique of, 257–259 Tolerable Upper Intake Level (UL), 48 Toluene (methylbenzene), 288–289 Tomography, 79–80 See also Positron emission tomography (PET) Topoisomerases, supercoiling and, 511 Torr, definition, 192 Torricelli, barometer inventor, 192 Trace elements, 48–50 Transamination, definition, 571 process of, 571–572 Transcription, definition, 514 control of, 522–523 genetic code, 518 process of, 517–520 reverse, 514, 521 Trans fats, health issues, 435–436 Transfer RNA (tRNA) amide bonds and, 313 characteristics of, 518 in protein synthesis, 519 trans isomers See also Trans fats, health issues in organic compounds, 287, 289–290 Transition elements, 56 Transition metals, 56 ion formation, 91 naming, 91 Translation (protein synthesis), definition, 514 steps of process, 520–522 Trehalose, 393 Trenbolone, structure of, 449 Triacylglycerides See Triglycerides Triclosan, 354–355 Triethylamine (N,NDiethylethanamine) naming of, 308 properties of, 310 Triglycerides, definition, 429 catabolism of, 566–569 digestion of, 549–550 and oxidation, 431, 566 reactions of, 431–435 structures and properties of, 429–431 Trigonal molecular shape, 126, 127 Trimethylamine (N,NDimethylmethanamine), properties of, 310 Trioses, classification of, 372, 373 Tripeptides, definition, 464 characteristics of, 464–465 Triple bonds in covalent bonding, 101–102 in unsaturated hydrocarbons, 287–290 Triplet code, characteristics of, 519 Tritium, hydrogen isotope, 52 Troponin I, in myocardial infarction, 489 Truvia, as sugar substitute, 400, 401 Trypsin activation of, 488 in protein digestion, 549 Trypsinogen, as zymogen, 488 Tryptophan (Trp) as essential amino acid, 573 structure of, 460 Tube wells, 80 Tympanic membrane thermometers, 21 Tyrosine (Tyr), structure of, 461, 463 U.S Food and Drug Administration (FDA), trans fats and, 435 Ultraviolet (UV) radiation, damage from, 139 Underwater weighing, 18, 19 Unit conversions, use of, 22 Units of measurement, common measurements, 9–12 Unsaturated fatty acids formation of, 571 properties of, 422–423 Unsaturated hydrocarbons, definition, 287 naming of, 288–289 structures and properties of, 287–288 Unsaturated solutions, definition, 216 Unsaturated triglycerides, characteristics of, 429–431 Uracil (U), structure of, 501 Uranium, 47 Uranium-235, fission reaction of, 70 Urea cycle, 572 Urease as cofactor, 481 specificity of, 478 Uric acid, and nitrogenous waste, 572 Uridine, structure of, 502 Uridine 5´-diphosphate (UDP), 544 Uridine 5´-monophosphate (UMP), 544 Uridine 5´-triphosphate (UTP) in glycogen metabolism, 558–559 in metabolism, 544, 546 Urine, specific gravity of, 27 Uronic acid, definition, 382 Urushiol, in poison ivy, 300 Valence electrons, definition, 65 characteristics of, 65 and ion formation, 93–95 Valence shell, 65 Valine (Val) as essential amino acid, 573 structure of, 460, 463 Valinomycin, as ionophore, 95 Vanillin, 136 Vapor pressure, definition, 194 temperature and, 195 Velocity, maximum, definition, 482 Verbascose, structure and properties of, 394, 395 Very low density lipoproteins (VLDLs), functions of, 442 Vioxx, effects of, 447 Viruses, characteristics of, 521 Volume conversion examples, 23 density and, 25–27 dilution and, 221–222 measurement of, 11 moles and, 199–200 pressure and, 197–198 temperature and, 198–199 Water in acid/base reactions, 242 and chemical reactions, 158–161 density and, 25–27 ionization of, 250–251 movement across membranes, 447–448 phase changes of, 8–9 solubility and, 212–215 specific heat of, 28 surface, contaminated, 80 vapor pressure of, 194–195 Waxes, definition, 427 characteristics of, 427–428 Weight conversion examples, 22–23 mass vs., 10–11 underwater, 18, 19 Weight loss, rapid, 28 Weight/volume percent, calculation of, 216 Wells, tube, 80 Work, definition, X-rays, 2, 79 in medicine, 79–80 radiation exposure from, 73 Xylitol, 398 Yeast, fermentation and, 555 Yeast tRNAPhe, 518 Yield, reaction, calculation of, 171–173 Zinc biochemical significance of, 49 dietary reference intake for, 50 Zwitterion, definition, 462 Zymogens, characteristics of, 488 THE ELEMENTS Atomic N ame Symbol number Actinium Aluminum Americium Antimony Argon Arsenic Astatine Barium Berkelium Beryllium Bismuth Bohrium Boron Bromine Cadmium Calcium Californium Carbon Cerium Cesium Chlorine Chromium Cobalt Copernicium Copper Curium Darmstadtium Dubnium Dysprosium Einsteinium Erbium Europium Fermium Fluorine Francium Gadolinium Gallium Germanium Gold Hafnium Hassium Helium Holmium Hydrogen Indium Iodine Iridium Iron Krypton Lanthanum Lawrencium Lead Lithium Livermorium Lutetium Magnesium Manganese Meitnerium Ac Al Am Sb Ar As At Ba Bk Be Bi Bh B Br Cd Ca Cf C Ce Cs Cl Cr Co Cn Cu Cm Ds Db Dy Es Er Eu Fm F Fr Gd Ga Ge Au Hf Hs He Ho H In I Ir Fe Kr La Lr Pb Li Lv Lu Mg Mn Mt Atomic weight 89 (227) 13 26.98154 95 (243) 51 121.760 18 39.948 33 74.92160 85 (210) 56 137.327 97 (247) 9.012182 83 208.9804 107 (264) 10.811 35 79.904 48 112.411 20 40.078 98 (251) 12.0107 58 140.116 55 132.9054 17 35.453 24 51.9961 27 58.9332 112 (285) 29 63.546 96 (247) 110 (281) 105 (262) 66 162.50 99 (252) 68 167.259 63 151.964 100 (257) 18.99840 87 (223) 64 157.25 31 69.723 32 72.64 79 196.9665 72 178.49 108 (269) 4.00260 67 164.93032 1.00794 49 114.818 53 126.9045 77 192.217 26 55.845 36 83.80 57 138.9055 103 (262) 82 207.2 6.941 116 (293) 71 174.967 12 24.3050 25 54.93805 109 (268) Atomic N ame Symbol number Mendelevium Mercury Molybdenum Neodymium Neon Neptunium Nickel Niobium Nitrogen Nobelium Osmium Oxygen Palladium Phosphorus Platinum Plutonium Polonium Potassium Praseodymium Promethium Protactinium Radium Radon Rhenium Rhodium Roentgenium Rubidium Ruthenium Rutherfordium Samarium Scandium Seaborgium Selenium Silicon Silver Sodium Strontium Sulfur Tantalum Technetium Tellurium Terbium Thallium Thorium Thulium Tin Titanium Tungsten Ununtrium2 Ununpentium2 Ununseptium2 Uranium Vanadium Xenon Ytterbium Yttrium Zinc Zirconium Md Hg Mo Nd Ne Np Ni Nb N No Os O Pd P Pt Pu Po K Pr Pm Pa Ra Rn Re Rh Rg Rb Ru Rf Sm Sc Sg Se Si Ag Na Sr S Ta Tc Te Tb Tl Th Tm Sn Ti W Uut Uup Uus U V Xe Yb Y Zn Zr 101 (258) 80 200.59 42 95.94 60 144.24 10 20.1797 93 (237) 28 58.6934 41 92.9063 14.0067 102 (259) 76 190.23 15.9994 46 106.42 15 30.97376 78 195.078 94 (244) 84 (209) 19 39.0983 59 140.90765 61 (145) 91 231.0359 88 (226) 86 (222) 75 186.207 45 102.9055 111 (272) 37 85.4678 44 101.07 104 (261) 62 150.36 21 44.95591 106 (266) 34 78.96 14 28.0855 47 107.868 11 22.98977 38 87.62 16 32.065 73 180.9497 43 (98) 52 127.60 65 158.92534 81 204.383 90 232.0381 69 168.93421 50 118.710 22 47.867 74 183.84 113 (284) 115 (288) 117 (294) 92 238.0289 23 50.9415 54 131.293 70 173.04 39 88.9058 30 65.39 40 91.224 For elements that not have stable isotopes, the mass number of the most stable isotope is given in parentheses Elements 113, 115, and 117 have been given temporary names, using the prefixes un (1), tri (3), pent (5), and sept (7) Atomic weight PERIODIC TABLE OF ELEMENTS Representative elements Representative elements Metals 1A Semimetals H Nonmetals 8A He 1.00794 2A 3A 4A 5A 6A 7A 4.00260 Li Be B C N O F 10 Ne 6.941 9.012182 10.811 12.0107 14.0067 15.9994 18.99840 20.1797 11 Na 12 Mg 13 Al 14 Si 15 P 16 S 17 Cl 18 Ar 22.98977 24.3050 26.98154 28.0855 30.97376 32.065 35.453 39.948 31 Ga 32 Ge 33 As 34 Se 35 Br 36 Kr Transition metals 8B 19 K 20 Ca 3B 21 Sc 4B 22 Ti 5B 23 V 6B 24 Cr 7B 25 Mn 26 Fe 27 Co 39.0983 40.078 44.95591 47.867 50.9415 51.9961 54.93805 55.845 58.9332 58.6934 63.546 65.39 69.723 72.64 74.92160 78.96 79.904 83.80 37 Rb 38 Sr 39 Y 40 Zr 41 Nb 42 Mo 43 Tc 44 Ru 45 Rh 46 Pd 47 Ag 48 Cd 49 In 50 Sn 51 Sb 52 Te 53 I 54 Xe 85.4678 87.62 88.9058 91.224 92.9063 95.94 [98] 101.07 102.9055 106.42 107.868 112.411 114.818 118.710 121.760 127.60 126.9045 131.293 55 Cs 56 Ba 57 *La 72 Hf 73 Ta 74 W 75 Re 76 Os 77 Ir 78 Pt 79 Au 80 Hg 81 Tl 82 Pb 83 Bi 84 Po 85 At 86 Rn 132.9054 137.327 [222] 28 Ni 1B 29 Cu 2B 30 Zn 138.9055 178.49 180.9479 183.84 186.207 190.23 192.217 195.078 196.9665 200.59 204.383 207.2 [208.9804] [209] [210] 87 Fr 88 Ra 89 †Ac 104 Rf 105 Db 106 Sg 107 Bh 108 Hs 109 Mt 110 Ds 111 Rg 112 Cn 113 Uut 114 Fi 115 Uup 116 Lv 117 Uus [223] [226] [227] [261] [262] [266] [264] [269] [268] [281] [272] [285] [284] [289] [288] [293] [294] 58 Ce 59 Pr 60 Nd 61 Pm 62 Sm 63 Eu 64 Gd 65 Tb 66 Dy 67 Ho 68 Er 69 Tm 70 Yb 71 Lu 144.24 [145] 150.36 151.964 157.25 158.92534 162.50 173.04 174.967 92 U 93 Np 94 Pu 95 Am 96 Cm 97 Bk 98 Cf 99 Es 100 Fm 101 Md 102 No 103 Lr [237] [244] [243] [247] [247] [251] [252] [257] [258] [259] [262] *Lanthanide elements †Actinide elements 140.116 140.90765 90 Th 91 Pa 232.0381 231.0359 238.0289 164.93032 167.259 168.93421 For elements that not have stable isotopes, the mass number of the most stable isotope is given in parentheses Elements 113, 115, and 117 have been given temporary names ... carboxylic acid O ‘ CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 C ¬OH Palmitic acid (hydrophobic; predominates at pH < 5) O ‘ − CH3CH2CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 C ¬O Palmitate ion... abbreviated organic style: They are not balanced and some reactants (Cl2 and Br2 in this case) and conditions (light) are written above or below the reaction arrow Cl CH3CH2CH3 Cl2 light CH3CH2CH2Cl and. .. a HCO2H CH3CO2H CH3CH2CO2H CH3(CH2)2CO2H CH3(CH2)3CO2H CH3(CH2)4CO2H Boiling Point (°C) Methanoic acid Formic acid Ethanoic acid Acetic acid Propanoic acid Butanoic acid Pentanoic acid Hexanoic