General, organic and biological chemistry integrated approach kennet w raymond 2ed

http://www.elsolucionario.net LIBROS UNIVERISTARIOS Y SOLUCIONARIOS DE MUCHOS DE ESTOS LIBROS LOS SOLUCIONARIOS CONTIENEN TODOS LOS EJERCICIOS DEL LIBRO RESUELTOS Y EXPLICADOS DE FORMA CLARA VISITANOS PARA DESARGALOS GRATIS General, Organic, and Biological Chemistry: An Integrated Approach, Second Edition Kenneth W Raymond John Wiley & Sons, Inc Every one of your students has the potential to make a difference And realizing that potential starts right here, in your course When students succeed in your course—when they stay on-task and make the breakthrough that turns confusion into confidence—they are empowered to realize the possibilities for greatness that lie within each of them We know your goal is to create an environment where students reach their full potential and experience the exhilaration of academic success that will last them a lifetime WileyPLUS can help you reach that goal WileyPLUS is a suite of resources—including the complete online text—that will help your students: • come to class better prepared for your lectures • get immediate feedback and context-sensitive help on assignments and quizzes • track their progress throughout the course www.wileyplus.com 88% of students surveyed said it improved their understanding of the material * TO THE INSTRUCTOR WileyPLUS is built around the activities you perform Prepare & Present Create outstanding class presentations using a wealth of resources, such as PowerPoint™ slides, image galleries, interactive learningware, and more Plus you can easily upload any materials you have created into your course, and combine them with the resources Wiley provides you with CATALYST With the 2nd edition of Raymond GOB, we are introducing an innovative online learning program called CATALYST The CATALYST assignments ask students to consider the key concepts and topics at hand from different perspectives; with different givens/desired responses required each time a new question is presented Create Assignments *Based on 7000 survey responses from student users of WileyPLUS in academic year 2006-2007 Automate the assigning and grading of homework or quizzes by using the provided question banks Student results will be automatically graded and recorded in your gradebook WileyPLUS also links homework problems to relevant sections of the online text, hints, or solutions— context-sensitive help where students need it most! in your class each day With WileyPLUS you can: Track Student Progress Keep track of your students' progress via an instructor's gradebook, which allows you to analyze individual and overall class results This gives you an accurate and realistic assessment of your students’ progress and level of understanding Now Available with WebCT and eCollege! Now you can seamlessly integrate all of the rich content and resources available with WileyPLUS with the power and convenience of your WebCT or eCollege course You and your students get the best of both worlds with single sign-on, an integrated gradebook, list of assignments and roster, and more If your campus is using another course management system, contact your local Wiley Representative “I studied more for this class than I would have without WileyPLUS.” Melissa Lawler, Western Washington Univ For more information on what WileyPLUS can to help your students reach their potential, please visit TM www.wileyplus.com/experience 84% of students would recommend WileyPLUS to their next instructors.* TO THE STUDENT You have the potential to make a difference! WileyPLUS is a powerful online system packed with features to help you make the most of your potential, and get the best grade you can! With WileyPLUS you get: A complete online version of your text and other study resources Study more effectively and get instant feedback when you practice on your own Resources like self-assessment quizzes, interactive learningware, and video clips bring the subject matter to life, and help you master the material Problem-solving help, instant grading, and feedback on your homework and quizzes You can keep all of your assigned work in one location, making it easy for you to stay on task Plus, many homework problems contain direct links to the relevant portion of your text to help you deal with problem-solving obstacles at the moment they come up 74% The ability to track your progress and grades throughout the term A personal gradebook allows you to monitor your results from past assignments at any time You’ll always know exactly where you stand If your instructor uses WileyPLUS, you will receive a URL for your class If not, your instructor can get more information about WileyPLUS by visiting www.wileyplus.com “It has been a great help, and I believe it has helped me to achieve a better grade.” Michael Morris, Columbia Basin College of students surveyed said it helped them get a better grade * GENERAL, ORGANIC, AND BIOLOGICAL CHEMISTRY An Integrated Approach SECOND EDITION GENERAL, ORGANIC, AND BIOLOGICAL CHEMISTRY An Integrated Approach SECOND Kenneth W Raymond Eastern Washington University John Wiley & Sons, Inc EDITION I-2 INDEX Ammonia, 148, 287, 298, 303, 335 Ammonium chloride, 215 Ammonium ions, 76, 97–98, 302, 303, 333–336, 533 Ammonium nitrate, 76 Amorphous solids, 167 AMP, see Adenosine 5Ј-monophosphate AMP (adenosine 5Ј-monophosphate), 474 Amphetamine, 346 Amphipathic compounds, 224–226, 256, 327 Amphoteric compounds, 290, 296 AMUs (atomic mass units), 28 Amylase, 239 Amylopectin, 419–420, 512 Amylose, 419–420, 512 Anabolic steroids, 275 Anabolism, 507, 510, 512 amino acid, 534 fatty acid, 532 Anaphylactic shock, 460 Androstenedione, 275 Anerobic conditions, 518 Anesthetics, 190 Anglerfish, 70 Anions, 75, 256 charge of, 64 defined, 64 naming, 76 Anomers, 407–409 Antacids, 287, 298, 312 Anthracene, 112 Anti-asthma drugs, 274 Anticodons, 487 Antidiuretic hormone (ADH), 163 Antigens, 422 Antihistamines, 320 Anti-inflammatory drugs, 382–383 Antilogarithms, 300 Antiparallel arrangement (DNA), 478 Antiparallel sheets (proteins), 442, 443 Antiseptics, 187–188 Arachidonic acid, 272 Ara h1/Ara h2/Ara h3 (peanut proteins), 460 Arginine (Arg), 435, 447, 534 Argon, 39, 69, 71 Aromatic compounds, 111, 121–124 Aromatic hydrocarbons, 121–124 Aromatic ring, 122 Arrhenius, Svante, 289 Arrhenius acids, 289 Arrhenius bases, 289 Arrhythmias (irregular heartbeat), 396, 422 Artificial sweeteners, 415–416 Asn, see Asparagine Asparagine (Asn), 343, 344, 435 Aspartame, 176, 177, 202, 415, 417 Aspartate, 526, 533 Aspartic acid (Asp), 435, 534 Aspirin, 102, 272, 455 Asthma, 274 -ate (suffix), 327 Atherosclerosis, 150, 271 Atmospheric pressure, 146–149, 160, 165, 166 Atom(s), 28–29, 64 Bohr’s theory of, 65 Dalton’s theory of, 28 electron arrangement in, 65–70 electron orbits, 65–66 formal charge, 94–102 ions of, 62–65 isotopes of, 33 mass number of, 32 moles, 37–38 neutral, 69 and octet rule, 71–72 Atomic mass units (AMUs), 28 Atomic notation, 32, 62 Atomic number, 32, 34, 69 Atomic orbitals, 66 Atomic symbols, 29–30, 32, 35 Atomic weight, 34–35, 39, 83 ATP, see Adenosine 5Ј-triphosphate Avobenzone, 124 Avogadro, Amedeo, 37, 156 Avogadro’s law, 156 Avogadro’s number, 37 Axillary temperature measurement, 16 B Background radiation, 44 Bacteria, 73, 453 Baking powder, 287 Baking soda, 287 Balanced equations: chemical, 178–181, 191–194 nuclear, 41–43 Barium chloride, 76 Barometer, 147 Base(s), 288–290 Brønsted-Lowry definition of, 289–290 and buffers, 306–308 characteristics of, 288 conjugate, 305–306 neutralization of, 303–304 organic, 472 pH scale for measuring strength of, 297, 298 strength of, 302 strong, 328 titration of, 304–305 water as, 296 Base pairing, 478, 492 Basic solutions, 297–298 Battery acid, 298 Beeswax, 259 Benedict’s reagent, 374–375, 405 Benedryl, 347 Bent molecular shape, 105, 106 Benzene/benzene rings, 112, 121–122 Benzo[a]pyrene, 122 Benzoic acid, 122, 328 Benzoquinone, 332 Benzoyl peroxide, 188 Benzyl alcohol, 122 Berkelium, Beryllium, 69 ␤ anomers, 407–409 ␤-chains, 448 Betadine, 184 ␤ oxidation spiral, 529 Beta particles, 41–45 ␤-sheets, 442, 443, 478 Bextra, 273 Bicarbonate ion, 201 Bile salts, 272, 273 Binary ionic compounds, 75 Binary molecules, 79–80 Binding sites, 444 Biochemical compounds, 224–227 Biofilms, 339–340 Bioluminescence, 70 Bismuth-213, 41 1,3-Bisphosphoglycerate, 516, 519, 520, 522, 528 Blood, 166–167, 201, 242, 298 capillary, 166 ketone bodies in, 531 Blood cells, 11, 221 Blood plasma, 73 Blood pressure, 149, 150 Blood serum, maintaining pH of, 308–311 Blood serum solutes, 228, 232 Blood sugar, see Glucose; D-Glucose Blood type, 414, 422 BMI, see Body Mass Index Body Mass Index (BMI), 13–14 Body temperature, measuring, 16 Bohr, Niels, 65 Bohr model, 65 Boiling point(s): of aldehydes, 373 and carbon chain length, 366 of disulfides, 366 of ethers, 366 of ketones, 373 of liquids, 165 of normal alkanes, 110–111 of selected alcohols, 125 of selected carboxylic acids, 125 of selected esters, 125 of sulfides, 366 of thiols, 366 of water, 140–141 Bombykol, 124 Bond(s): coordinate—covalent, 109 covalent, 77–78 double, 78–79, 123 glycosidic, 410–412 single, 78–79, 117, 123 triple, 78–79 types of, 104 Bond angles (shapes), 104–106 Boron, 34, 35 Boyle, Robert, 151 Boyle’s law, 151, 166 Brachial artery, 150 Brain cells, 520 BRCA1 gene, 492 BRCA2 gene, 492 Breast cancer, 492 Breathing, 166–167 Brewer’s yeast, 331 Bromides, 76, 217 Bromide ion, 303 Bromine, 30, 70, 71, 367 Bromine (Br2), 148 Bronchoconstriction, 347 Brønsted, Johannes, 289 Brønsted-Lowry definition (of acids), 289 Brown fat, 527 Buffers, 306–308 Bulk elements, 31 Butanal, 374 2-Butanamine, 341 Butane, 111, 112, 115, 117, 365 2-Butanethiol (s-butyl mercaptan), 364 Butanoic acid, 125, 324 1-Butanol (butyl alcohol), 125, 365 2-Butanol, 372 Butanone (methyl ethyl ketone), 374 2-Buten-1-thiol, 363 1-Butene, 112, 372 2-Butene, 372 cis-2-Butene, 123 trans-2-Butene, 123 sec-Butyldimethylamine (N,Ndimethyl-2-butanamine), 334 6-t-Butyl-4-ethyl-6-methyldecane, 114 Butyl heptanoate, 224 Butyl isopropyl ketone (2-Methyl3-heptanone), 373 s-Butyl mercaptan (2-butanethiol), 364 C °C, see Celsius Cabbage, 301 Cadaverine, 336 Caffeine, 322 Cal, see Calorie Calcium, 69 Calcium chloride, 79 Calcium hydroxide, 218 Calculations, significant figures in, 300 Calculators, 14 Calorie (cal), 7, 8, 141–142 cAMP (adenosine 3Ј,5Ј-cyclic monophosphate), 475 Cancer, 492 chemotherapy for, 242–243 radiation therapy for, 47–48 skin, 124 thyroid, 47 Capillaries, 221 Capillary blood, 166 Capsaicin, 325 Caraway, 343, 344 INDEX Carbohydrate(s), 397–421 chiral carbon atoms in, 400–401 monosaccharides, 398–409 oligosaccharides, 410–417 polysaccharides, 418–421 stereoisomers in, 400–401 as term, 397 Carbolic acid, 187–188 See also Phenol(s) Carbon, 37, 38, 71, 398 Carbon-12, 41 Carbonates, 217 Carbonate ion, 303, 312 Carbon atom(s): ␣, 331 alkane-type, 126 ␤, 331 hemiacetal, 406 structure of, 30 Carbon—carbon double bonds, 369 Carbon chain, and boiling point, 366 Carbon dioxide (CO2), 107, 148, 184–185, 201 Carbonic acid (H2CO3), 201, 302, 303 Carbonic anhydrase, 201 Carbon monoxide (CO), 186, 222 Carbon—oxygen double bonds, 377 Carbonyl group (C “ O), 126, 370, 379, 533 Carboxylic acid, 370 Carboxylate ions, 326–327 Carboxyl group (COOH), 126, 256, 434, 436, 440 Carboxylic acids, 125–127, 322–324, 374, 470 conjugate bases of, 326–327 decarboxylation of, 331 and ester formation, 329–331 functional groups, 126–127 and hydrogen bonds, 127 IUPAC rules, 327 pH/pKa of, 326 properties of, 127 and strong bases, 328 as weak organic acids, 326–327 Carboxylic acid sugars, 404 Carnauba wax, 259 Carnitine, 528 Carvone, 343, 344 Catabolism, 507, 510–511 amino acid, 533–534 fatty acid, 528–529 Catalase, 378, 451, 525 Catalysis, 451 Catalyst(s), 201 See also Enzyme(s) biochemical, 200 defined, 187 and equilibrium, 295 and rate of reaction, 451 Catalytic hydrogenation, 187–188, 262, 376–378 Catalyzed reactions, control of, 453–459 Catechin, 324, 325 Catechol, 326 Cations, 75 charge of, 62 defined, 62 naming, 76 Cayenne pepper, 325 Celebrex, 273 Cell membranes, lipids in, 266–267 Cellobiose, 410–412 Cellulose, 418–419 Celsius (°C), 7, Centi- (prefix), 10 Centrifugation, 238 Cephalin, see Phosphatidylethanolamine Cerebrosides, 269, 414 Cesium-137, 47 Chain reaction, 50 Charge(s): formal, 94–102 of subatomic particles, 28–29 temporary partial, 109–110 Charles, Jacques, 154 Charles’ law, 154–155 Chemical change, 74 Chemical composition, Chemical equations, 178 balanced, 191–194 balancing, 178–181 common balancing errors in, 181 interpreting reaction calculations, 178–181 Chemical properties, 74 Chemical reactions, see Reaction(s) Chemistry, definition of, Chemotherapy, 242–243 Chernobyl nuclear power plant, 44 Chili pepper, 325 Chiral (term), 341 Chiral carbon atoms, 342, 345, 346, 400–401, 406, 407 Chitin, 420 Chloramphenicol, 228, 344 Chloramphenicol palmitate, 228 Chlorides, 76, 217 Chloride ion, 303 Chlorine, 30, 71, 74, 367 Chloroform, 163 2-Chlorophenol (o-chlorophenol), 324, 325 Chloroprocaine, 190 Chlorpheniramine, 347 Chlor-Trimeton, 347 Cholesterol, 106, 270–272, 275, 276, 362 Chondroitin 4-sulfate, 421 Chromatin, 480 Chromium, 72 Chromosomes, 480 Chronic wasting disease, 118 Chylomicrons, 271 Chymotrypsin, 439, 449, 458, 513 ␲-Chymotrypsin, 458, 459 Chymotrypsinogen, 439, 458, 459 Cinnamaldehyde, 363 Circular metabolic pathways, 506 Cis double bonds, 254, 255, 261, 275 Cis isomers, 120, 123 Citrate, 190, 517, 523, 534 Citrate synthase, 523 Citric acid, 287 Citric acid cycle, 189, 522–524 and amino acid catabolism, 534 and anabolism, 512 and ATP generation, 530 and catabolism, 510 circularity of, 522–523 control of, 524 and gluconeogenesis, 520 and glycolysis, 517, 518 heat produced by, 527 and ketone bodies, 531 and rotenone, 535 Citronellol, 362 CMP (cytidine 5Ј-monophosphate), 474 CoA, see Coenzyme A Cobalt, 76 Cobalt-60, 47 Cobalt(II) chloride, 218 Codons, 486–487 Coefficients (in chemical equations), 178, 180–181 Coenzyme A (CoA), 452, 509, 510, 518, 529, 530, 532 Coenzymes, 452 Coenzyme Q, 526 Cofactors, 452 Colds, 489 Collagen, 441, 447 Colloids, 238, 268 Colon cancer, 492 Combined gas law, 157 Combustion, 184–185 Common names, 121, 323 Common units, 6–7 Competitive inhibitors/inhibition, 454–456 Complementary base pairings, 478–479 Complementary bases (DNA), 480 Complex proteins, 445 Compound(s), 61, 222–224 See also Organic compounds amphipathic, 224–226, 256, 327 amphoteric, 290, 296 aromatic, 111, 121–124 biochemical, 224–227 conjugate, 290 defined, 74 hydrocarbons, 110–114 hydrophilic, 224–225 hydrophobic, 224–225 insoluble, 215 ionic, 74–76 soluble, 215 uses of, 76 Computed tomagraphy (CT), 49 I-3 Concentration(s), 228–235 defined, 228 and diffusion, 240, 242 equivalent, 233–234 and molarity, 231–235 and osmosis, 240–241 parts per thousand/million/billion, 230 percent, 229 of solutions, 228–235 Concentration units, 235 Condensed structural formulas, 101 Cones (retina), 129 Conformations (of molecules), 117 Congestive heart failure, 422 Conjugates, 290 Conjugate acid(s), 336, 436 Conjugate base(s): acids and (list), 303 of carboxylic acids, 326–327 effect of pH on acid and, 305–306 of phenols, 328 Constitutional isomers, 115 Control rods, 51 Conversions: of atoms and moles, 37–38 mass to mole, 39 temperature, 19 unit, 15, 18 Conversion factors, 15, 17–18, 37–38, 142 Convulsions, 423 Coolant (nuclear reactor), 51 Cooperative binding, 448 Cooperativity, 457 Coordinate—covalent bonds, 109 Copper, 30 Copper chloride, 76 Corn syrup, 416 Cortisol, 272 Cortisone, 272, 273 Cosmic rays, 44 Counting units, 37–38 Coupled reactions, 506 Covalent bonds, 77–78 polar, 103–107 and polyatomic ions, 97–98 structural formulas, 94–95 Covalent crystalline solids, 167–168 Covalent modification, 457–458, 521 COX-1, 272–273 COX-2, 272–273 Creativity (in scientific process), Crenation, 240 Creutzfeldt-Jakob disease, 118 Cristae (mitochondria), 511 Critical mass, 50 Crystal lattice, 75, 216–217 Crystalline solids, 167–168 CT (computed tomagraphy), 49 Ctenocephalides felis, 340 C-terminus, 438 Cyanide ion, 303 I-4 INDEX Cyclases, 475 Cyclic hemiacetals, 406–409 Cyclic nucleotides, 475 Cycloalkanes, 118–120 Cyclooxygenase, 272 Cysteine (Cys), 363, 435 Cystic fibrosis, 492 Cytidine, 473 Cytidine 5Ј-monophosphate (CMP), 474 Cytoplasm, 485, 527 Cytosine (C), 472, 474, 476, 477 D Dalton, John, 28 Dalton’s atomic theory, 28 Dalton’s law of partial pressure, 159 dAMP (deoxyadenosine 5Јmonophosphate), 474 Dash-wedge bond notation, 342 dCMP (deoxycytidine 5Јmonophosphate), 474 Decarboxylation, 331 Deci- (prefix), 10 Decimal places, 9–10, 15 Decomposition reactions, 182 Dehydration, 164, 190, 372–373 Dehydrogenation, 449 Deka- (prefix), 10 Denaturation, 449, 480–481 Density, 162–163 Dental fillings, 80–81 Deoxyadenosine, 473 Deoxyadenosine 5Ј-monophosphate (dAMP), 474 Deoxycytidine, 473 Deoxycytidine 5Ј-monophosphate (dCMP), 474 Deoxyguanosine, 473 Deoxyguanosine 5Ј-monophosphate (dGMP), 474 Deoxyhemoglobin, 169, 448 Deoxymyoglobin, 295 ␣-D-2-Deoxyribofuranose, 408 ␤-D-2-Deoxyribofuranose, 408, 471 Deoxyribonucleic acid (DNA), 402, 469, 477 denaturation of, 480–481 larger structures involving, 480 mitochondrial, 512 and mutation, 491–492 recombinant, 492–494 renaturation of, 480, 481 replication of, 481–483 in saliva, 239 structure of, 477–480 Deoxyribonucleosides, 472, 473 Deoxyribonucleotides, 474 2-Deoxyribose, 471 D-2-Deoxyribose, 401–402, 408, 411 Deoxy sugars, 402–403 Deoxythymidine, 473 Dephosphorylation, 457–458 Deposition, 141 Desaturase enzymes, 532 Dexedrine, 346 Dextrorotatory isomers, 343 Dextrose, see D-Glucose dGMP (deoxyguanosine 5Јmonophosphate), 474 Diabetes, and ␤-keto acids, 331 and ketone bodies, 331 urine testing for, 405 Diallyl disulfide, 363 Dialysis, 242 Diaphragm, 166, 167 Diastereomers, 345, 400–401 Diastolic pressure, 150 Diatomic molecules, 78 Dichlone (fungicide/herbicide), 332 Dietary Reference Intakes (DRIs), 31–32 Diethyl disulfide, 371 N,N-Diethylethanamine (triethylamine), 334 Diethyl ether, 364, 365 Diethyl sulfide, 365, 367 Diffusion, 240, 242, 276–277 Digestion, 512–514 Digitalis, 422 Digital thermometers, 16 Digitoxin, 422, 423 Digoxin, 422, 423 Dihydrogenphosphate ion (H2PO4 Ϫ), 65, 302, 303, 470 Dihydroxyacetone phosphate, 516, 519, 522, 526 Dilution, 236 N,N-Dimethyl-2-butanamine (secbutyldimethylamine), 334 1,2-Dimethylbenzene, 122 1,3-Dimethylbenzene, 122 1,4-Dimethylbenzene, 122 2,2-Dimethylbutane, 115 2,3-Dimethylbutane, 115 1,2-Dimethylcyclopentane, 119 1,3-Dimethylcyclopentane, 119 Dimethyl ether, 365, 367 3,4-Dimethylheptane, 114 Dimethyl ketone, see Propanone N,N-Dimethylmethanamine (trimethylamine), 336 Dimethyl sulfide, 364, 365, 371, 382–383 Dimethyl sulfoxide (DMSO), 371, 382–383 Dinitrogen pentoxide, 79 Dipeptides, 437, 438 Diphenhydramine, 322, 347 Dipivefrin, 228 Dipole-dipole forces/interactions, 109, 335, 373, 444, 445 Dipropylamine, 334 Dipropyl disulfide, 364 Dipropyl ether, 365 Dipropyl sulfide, 365 Disaccharides, 410–412 Dismutation reaction, 378 Dissociation, 302 Disulfides, 362, 366 Disulfide bonds, 445, 447 Disulfide bridges, 371, 445, 459 Disulfiram, 376 Diving mammals, 295 DMSO, see Dimethyl sulfoxide DNA, see Deoxyribonucleic acid DNA fingerprinting, 494–495 DNA polymerases, 483, 494–495 DNA replication, 481–483 DNA viruses, 489 D notation, 400 Docosahexaenoic acid, 257 Dolomite, 220 Dolphins, 295 Double bonds, 78–79, 254, 255, 261, 275 Double helix, 478 Double replacement reactions, 182 Drain cleaners, 287 DRIs, see Dietary Reference Intakes Drugs in the environment, 382 Dry ice, 141 dTMP (thymidine 5Ј-monophosphate), 474 3,4-Dymethyl-1-pentyne, 122 Dynamometer, E Eact , see Activation energy Ecamsule, 124 Eggplant, 301 Ehlers-Danlos syndrome, 447 Eicosanoids, 272–274 Eicosapentaenoic acid, 257 Einstein, Albert, 29 Einsteinium, 29 Electrolytes, 214 Electromagnetic radiation, 43, 65, 125 Electrons, 28–29, 62–64 arrangement of, 65–70 clouds of, 62 in covalent bonds, 77–78 determining number of, 34 energy level and maximum number of, 67 as energy waves, 66 and octet rule, 71–72 orbits of, 65–66 valence, 68, 69, 71–72, 77 Electron clouds, 66 Electron dot structures, 69, 71, 72, 77–78, 94 Electron transport chain, 505, 510–512, 524–527, 529, 530, 535 Elements, 29–31, 83 actinide, 36 atomic symbols for, 29–30 atomic weights of, 39 bulk, 31 defined, 29 gaseous, 148 groups of, 36 isotopes of, 33–34 lanthanide, 36 metals, 34 names of, 29, 30 nonmetals, 34 periodic table of, 34–35, 68–69, 148 periods of, 36 properties of, 37 pure, 61 representative, 36, 69 semimetals, 34 trace, 31 transition, 36 Elongation (protein translation), 487–488 Emission spectrum (hydrogen), 65 Emulsifying agents, 268 Emulsion, 268 Enamines, 333–334 Enantiomers, 341–346 defined, 341 of glyceraldehyde, 400 physical properties of, 343 Endonucleases, 483, 492 Endoplasmic reticulum, 485 Endothermic (term), 144 End point (titration), 304 Energy, 5, 6, 143 activation, 198–199, 451 defined, 5, 143 free, 143, 145, 198–200 and glycolysis, 518–519 heat, 141–142 infrared, 16 kinetic, 5–6, 140, 161, 449, 451 measurement of, 7, potential, 5–6 as waves, 43 Energy diagrams, 198–200 Energy levels (electrons), 65 Enoic acids, 323 Enolase, 516 Enteropeptidase, 459 Enthalpy, 143–146, 198 Entropy, 143–146 Environment, drugs in the, 382 Enzyme(s), 449–453 active sites of, 451 allosteric, 457 and biological catalysts, 449 and catalysis, 451 as catalysts, 200 and coenzymes, 452 and cofactors, 452 and control of catalyzed reactions, 453–459 and covalent modification, 457–458 defined, 187 high-temperature, 452–453 and inhibitors, 454–456 Michaelis-Menten, 453–454 naming of, 449–450 and pH, 452, 453 protective, 378 specificity of, 450–451 substrates of, 449, 451 and temperature, 452–453 and zymogens, 458–459 Enzyme-substrate complex, 451, 454 INDEX Ephedrine, 337, 346 Ephedrine hydrochloride, 337 Epinephrine (adrenaline), 227–228, 346, 367–368 Equal™, 417 Equations, chemical, see Chemical equations Equilibrium, 290–293 and catalysts, 295 defined, 291 and Le Châtelier’s principle, 293–294 in solids, 292 Equilibrium constant (Keq), 291–293, 301, 302 Equivalent (Eq), 233–234 Escherichia coli, 489–490 Essential amino acids, 534 Essential fatty acids, 272, 532 Esters, 125–127, 329–331 and flavors/odors, 128 functional groups, 126–127 and hydrogen bonds, 127 naming, 330 properties of, 127 Estradiol, 272, 273 Estrone, 344 Ethambutol (in tuberculosis treatment), 344 Ethanal (acetaldehyde), 331, 373, 374, 376, 518 Ethanamine (ethylamine), 334, 336 Ethane, 107, 111, 112, 365 Ethanethiol (ethyl mercaptan), 78, 365, 371 Ethanoic acid (acetic acid), 79, 125, 224, 302, 303, 322–324, 326, 376 Ethanol (ethyl alcohol, grain alcohol), 125, 222, 331, 364, 365, 376, 518 Ethene, 112 Ethers, 365–366 boiling points of, 366 flammability of, 372 physical properties of, 365 preparation of, 367 structure of, 362 5-Ethyl-3,3-dimethyloctane, 114 3-Ethyl-4-methylhexanoic acid, 323 Ethyl alcohol, see Ethanol Ethylamine, 336, 337 Ethylammonium chloride, 337 Ethyl benzoate, 122 Ethyl butanoate, 125 Ethyl chloride, 367 Ethylene, 84, 121 Ethylene gas, 193 Ethyl ethanoate, 125 Ethyl iodide, 367 Ethyl mercaptan, see Ethanethiol Ethyl methanoate, 125, 224 Ethylmethylamine (Nmethylethanamine), 336 Ethyl methyl ether, 364 3-Ethyl-2-methylheptane, 114 4-Ethylphenol (p-ethylphenol), 324, 325 Ethyl propanoate, 125 Eugenol, 322 Exact numbers, 12 Excited state, 65, 70 Exoskeleton, 420 Exothermic (term), 144 Experiments, 2–3 Exponents, 9–10 Expressed genes, 489–490 Eye(s): vitreous humor of, 421 watery, 347 F °F, see Fahrenheit Facilitated diffusion, 276–277 Factor label method, 15, 17, 142 FAD, 509, 510, 529 FADH2 , 452, 509, 525, 529, 530 Fahrenheit (°F), 7, “Fake fat,” 266 Fat(s): and Body Mass Index, 13–14 brown, 527 “fake,” 266 trans, 265 Fatty acids, 254–258, 513, 528 essential, 532 monounsaturated, 254–256 omega-3, 257–258 and pH, 327 polyunsaturated, 254–258 saturated, 254–256 unsaturated, 254–256 Fatty acid anabolism, 532 Fatty acid catabolism, 528–529 Fatty acid residue, 258 Fatty acyl-ACP, 532 FDA, see U.S Food and Drug Administration Fe2ϩ, 452 Feedback inhibition, 457 Fermentation, alcoholic, 331, 518 Fibrinogen, 232–233 Fibrous proteins, 441, 447 Fireflies, 70 Fisher projections, 400 Fission, 50–51 defined, 50 in nuclear reactors, 51–52 5Ј-terminus, 476, 477 Five-membered rings, 407 Flavin adenine dinucleotide, 509 Flavr-Savr tomatoes, 468, 496 Flea control, 340 Fluid mosaic model, 276 Fluoride, 84–85 Fluoride ion, 303 Fluorine, 69, 71, 77 Fluorine-18, 30, 42, 53 Fluoroapatite, 84–85 2-Fluorobutane, 102 fMET, see N-Formylmethionine Folate, 454 Food allergies, 460 Food preservatives, 328 Foot (unit), 7, Formal charges, 94–102 Formaldehyde, see Methanal Formic acid, see Methanoic acid Formula weight, 81–82 of ionic compounds, 81–82 and mole/mass conversion, 82 N-Formylmethionine (fMET), 486–487 Foxglove, 396, 398, 422–423 Francium, 41 Free energy, 143, 145, 198–200 Freezing point (water), 140–141 D-Fructofuranose, 408 Fructose, 225, 415, 416, 519 D-Fructose (fruit sugar), 402, 412, 416 anomers of, 408 isomers of, 405 Fructose 1,6-bisphosphate, 515, 519, 520, 522 Fructose 6-phosphate, 515, 519, 520, 522, 528 Fruit sugar, see D-Fructose L-Fucose, 403, 422 Fuel rods, 51 Fumarase, 523 Fumarate, 523, 534 Functional groups, 126–127 Furanose, 407, 408 Fusion: heat of, 140–141 nuclear, 52–53 G D-Galactopyranose, 407 Galactopyranose residues, 417 Galactose, 415, 519 D-Galactose, 400–402, 407, 412, 414, 422 Galactosemias, 402 ␣-Galactosidase, 417 ␤-Galactosidase, 417, 489–490, 512 Gamma rays, 40–42, 44, 45, 49 Gangliosides, 269, 414 Garlic, 363 Gas(es), 4–5, 146–161 constant, 157 defined, ideal, 157 inert, 36, 148 partial pressure of, 158–161 and pressure, 146–149, 158–161 and pressure-temperature relationship, 152–153 solubility of, in water, 221 Gaseous elements, 148 Gas gangrene, 222 Gas laws, 150–157, 159 Gasoline, 117 Gas producing reactions, 219–220 Gas solubility, 221 Gastric fluid, 298, 312 Gay-Lussac, Joseph Louis, 152 Gay-Lussac equation, 153 Gay-Lussac’s law, 152–153 I-5 Gene(s): defined, 477 expressed, 489–490 Genetically engineered insulin, Genetically modified (GM) foods, 468, 496 Genetic code, 486, 487 Genetic diseases, 492 Gentisic acid, 324, 325 Geometric isomers, 119–120, 123, 341 cis, 120, 341 trans, 120, 341 Gestrinone, 277 Gibbs, Willard, 145 Gibbs free energy, 145 Giga- (prefix), 10 Glaucoma, 227 Globular proteins, 441, 444, 448 Glucagon, 522 Gluconeogenesis, 519–521, 526 D-Gluconic acid, 404 ␣-D-Glucopyranose, 406, 410 ␤-D-Glucopyranose, 406 ␣-Glucopyranose residues, 419 D-Glucosamine, 403 D-Glucosaminopyranose, 407 Glucose (blood sugar), 4, 225, 232, 346, 375, 397, 415–417, 490, 515, 519, 520, 527, 528 catabolism of, 514–517 conversion of, 515 detection of, in urine, 405 and glucagon, 522 radioactively-labeled, 53–54 D-Glucose (dextrose, blood sugar), 400–406, 410–412, 414, 416 L-Glucose, 400–402 Glucose isomerase, 416 Glucose oxidase, 405 Glucose 1-phosphate, 521, 522 Glucose 6-phosphate, 515, 519–522, 528 Glucose testing, Glucose-UDP, 522 D-Glucuronate, 421 D-Glucuronic acid, 404 Glutamate, 532, 533 Glutamic acid (Glu), 435, 447, 492, 532, 534 Glutamine (Gln), 435 Glyceraldehyde, 400 Glyceraldehyde 3-phosphate, 516, 519, 520, 522, 528 Glyceraldehyde 3-phosphate dehydrogenase, 516 Glycerol, 161, 162, 512–514, 528 Glycerol 3-phosphate, 526, 528 Glycerophospholipids, 267–269, 276 Glycine (Gly), 83, 225, 434, 438, 447 Glycogen, 420, 519 breakdown of, 458 metabolism of, 521–522 Glycogenesis, 521–522 I-6 INDEX Glycogenolysis, 521–522 Glycogen phosphorylase, 458, 522 Glycogen synthase, 522 Glycolipids, 268–270, 275, 276, 414 Glycolysis, 511, 514–519, 522, 526, 527 and catabolism, 510 control of, 517 and energy, 518–519 net reaction for, 516 and non-glucose monosaccharides, 519 and pyruvate, 518 as spontaneous, 518 step by step, 515 Glycoproteins, 414 Glycorol 3-phosphate, 526 Glycosides, 410, 422, 471 N-Glycoside, 471 Glycosidic bonds, 410–412 ␣–(1S4)Glycosidic bonds, 419–420, 512 ␣–(1S6)Glycosidic bonds, 419–420 ␤–(1S2)Glycosidic bonds, 412 ␤–(1S3)Glycosidic bonds, 421, 422 ␤–(1S4)Glycosidic bonds, 411, 417, 421 ␤–(1S6)Glycosidic bonds, 417 GM foods, see Genetically modified foods GMP (guanosine 5Ј-monophosphate), 474 Gout, 242 Grain alcohol, see Ethanol Gram (unit), 6–9 Grapefruit juice, 298 Grapes, 301 Graphite, 168 Gravity: law of, specific, 163–164 Ground state, 65, 70 Groups (periodic table), 36 GTP, see Guanosine 5Ј-triphosphate (GTP) Guanine (G), 472, 474, 476, 477 Guanosine, 473 Guanosine 5Ј-monophosphate (GMP), 474 Guanosine 5Ј-triphosphate (GTP), 508, 510 Guanosyl, 508 H Half-life, 45–46 Halogens, 36 Hard water, 220 HCl, see Hydrogen chloride HDLs, see High density lipoproteins Headaches, 347, 396 Heart: arrhythmias of, 396, 423 muscle of, 422–423 Heart failure, 423 Heart rate, increased, 423 Heat: from brown fat cells, 527 change in (⌬H), 144 energy, 141–142 of fusion, 140–141 specific, 142 of vaporization, 140, 142–143 Hecto- (prefix), 10 Helium, 19, 61, 67, 68, 71, 156 Heme group, 445 Heme prosthetic group, 448 Hemiacetal(s), 379 and acetals, 380–381 carbon atoms, 406 cyclic, 406–409 formation of, in monosaccharides, 406 Hemiketals, 379 Hemodialysis, 242 Hemoglobin, 153, 166, 201, 222, 445, 448, 492 Hemolysis, 240 Henna, 333 Henry, William, 221 Henry’s law, 221 Heptadecane, 111 Heptanoic acid, 324 Heptoses, 399 Heroin, synthetic, 355 Herpes, 489 Heterocyclic amines, 335 Heterogeneous mixtures, 214 Heteropolysaccharides, 418, 420 Hexane, 115, 222, 223 Hexanoic acid, 324 2-Hexanone (methyl butyl ketone), 374 Hexokinase, 515, 517 Hexoses, 399 High blood pressure, 150 High density lipoproteins (HDLs), 257, 265, 270–271 High fructose corn syrup, 416 High-temperature enzymes, 452–453 Histamine, 320, 347, 460 Histidine (His), 435, 534 Histones, 480 Homocystinuria, 447 Homogeneous mixtures, 214 Homopolysaccharides, 418–420 Hormones, 84 ethylene plant, 84 steroid, 272, 273, 275 HSDHs, see Hydroxysteroid dehydrogenases Humans, 295 Human body, elements in, 31 Human growth hormone, 494 Hyaluronic acid, 421 Hydorcarbon tails, 256 Hydration, 189–190 Hydrobromic acid, 288, 303 Hydrocarbons, 110–114, 120–122, 222 catalytic hydrogenation of, 187–188 naming, 121–122 polycyclic aromatic, 122 Hydrochloric acid, 288, 302, 303, 337 Hydrocyanic acid, 302, 303 Hydrogensulfate ion, 303 Hydrofluoric acid, 302, 303 Hydrogen, 33, 65, 67, 68 Hydrogenation: catalytic, 187–188, 262 partial, 261–262 Hydrogen bonds/bonding, 140, 168, 222, 324, 325, 447 in alcohols, 365 in amines, 335–336 and carboxylic acids, 324 in cellulose, 418 defined, 108 in hemoglobin, 448 and physical properties, 127 and tertiary structure, 444–445 Hydrogencarbonate ion, 65, 302, 303, 312 Hydrogen chloride (HCl), 79, 219 Hydrogen emission spectrum, 65 Hydrogen fluoride, 79 Hydrogen peroxide (H2O2), 378 Hydrogenphosphate ion (HPO4 2Ϫ), 65, 302, 303, 470 Hydrogensulfate ion, 303 Hydrogen sulfide (H2S), 79, 219 Hydroiodic acid, 288, 303 Hydrolysis, 189, 513 Hydronium ion, 303 Hydrophilic compounds, 224–225, 398 Hydrophilic heads, 275 Hydrophobic compounds, 224–225 Hydrophobic effect, 445 Hydrophobic forces, 444–445 Hydrophobic interactions, 447, 449 Hydrophobic tails, 275 Hydroquinones, 326, 332, 370 Hydroxides, 217, 303 Hydroxide ion, 312, 336 Hydroxyapatite, 84 3-Hydroxybutyrate, 531 Hydroxyl groups ( ¬ OH), 126, 327, 447 Hydroxyproline, 447 2-Hydroxypropanonic acid (lactic acid), 302, 342 Hydroxysteroid dehydrogenases (HSDHs), 377–378 Hyperbaric chamber, 222 Hyperbaric medicine, 222 Hypertension (high blood pressure), 150 Hyperthyroidism, 47 Hypertonic solutions, 240, 241 Hypotheses, 2–3 Hypotonic solutions, 240, 241 I -ic, 327 Ice: dry, 141 melting point of, 140–141 Ideal gases, 157–158 Ideal gas law, 157–159 Imaging, medical, 49 Immune response, 422 Inactive repressor protein, 490 Inert gases, 36, 71, 148 Inflation pressure (of tires), 152 Influenza, 489 Information flow (DNA), 481 Infrared (IR) energy, 16 Infrared (IR) light, 65 Inhibition/inhibitors: competitive, 413–414 competitive vs noncompetitive, 454–456 defined, 454 and enzyme catalyzed reactions, 454–456 noncompetitive, 456 reversible, 454 Initiation (protein translation), 487, 488 Inner membrane (mitochondria), 511, 525, 526 Insect wax, 259 Insoluble compounds, 215 Insulin, 4, 417, 442, 445, 494, 521–522 Intercostal muscles, 166, 167 Intermembrane space (mitochondria), 511 International Thermonuclear Experimental Reactor (ITER), 52–53 Intracellular fluid, 73 Invert sugar, 415, 416 Iodides, 217 Iodide ion, 303 Iodine, 71, 188, 367 Iodine-131, 34, 43, 47–48 Ions, 62–65 See also specific headings, e.g.: Ammonium ions isoelectronic, 71 monoatomic, 62–63 negatively charged, 64 nitrate, 97, 98 polyatomic, 64–65, 97 positively charged, 62 reactions of, in aqueous solutions, 216–220 spectator, 218 Ion—dipole interactions, 109 and denaturation, 449 and tertiary structure, 444, 445 Ionic bonds, 75, 109, 167–168 Ionic compounds, 74–76, 83 binary, 75 formula weight of, 81–82 naming, 76 polyatomic ions, 75–76 Ionic crystalline solids, 167–168 Ionic equations, 218 Ionization (of water), 296–297 Ionophores, 73 Ion transport, 73 IR, see under Infrared Iridium-192, 43 INDEX Iron, 76 Irregular heartbeat, 396, 423 Irreversible inhibitors, 454 Isocitrate, 189, 523, 534 Isocitrate dehydrogenase, 523 Isoelectric point (pI), 436 Isoelectronic ions, 71 Isoleucine (Ile), 434, 534 Isomers: cis vs trans, 120 constitutional, 115–117 dextrorotatory vs levorotatory, 343 of D-fructose, 405 geometric, 119–120, 123 stereoisomers, 118–119, 123 Isopropyl alcohol (rubbing alcohol, 2-propanol), 141, 143, 161, 364, 369 5-Isopropyl-2-octyne, 122 Isotonic solutions, 240, 241 Isotopes, 33–34 Itching, 347 ITER, see International Thermonuclear Experimental Reactor IUPAC naming rules, 113–115 alcohols, 364–365 aldehydes, 373 alkanes, 114 alkenes, 119 and alkyl groups, 113 alkynes, 119 amine conjugate acids, 336 for amines, 333–334 carboxylic acids, 323, 327 cycloalkanes, 119 disulfides, 364 ethers, 364 hydrocarbons, 121–122 ketones, 373 and parent chain, 113 and point of attachment, 113 quaternary (4°) ammonium ions, 334 sulfides, 364 thiols, 364 J Jasmone, 363 Joule (J), K K, see Kelvin Ka (acidity constant), 292, 302 Kadsurenone, 362 Kelvin (K), 7, 8, 152, 153, 155 Keq , see Equilibrium constant Keratin, 441 ␣-Keratin, 447 Ketoacidosis, 531 ␣-Keto acids, 331l, 533 ␤-Keto acids, 331 ␣-Ketoglutarate, 523, 533, 534 ␣-Ketoglutarate dehydrogenase, 523 Ketoheptoses, 399 Ketone(s), 363, 370, 398, 399 and acetal formation, 379–380 boiling points of, 373 and hemiacetal formation, 379 physical properties of, 374 reactions of alcohols with, 379–381 reduction of, 376–377 structure of, 363 Ketone bodies, 331, 531, 534 Ketoses, 398, 399 Ketosis, 531 Ketotetrose, 398 Kidneys, 242 Kidney dialysis, 242 Kilo- (prefix), 10 Kilogram (unit), 6–8 Kinases, 457 Kinetic energy, 5–6, 140, 161, 449, 451 KM (Michaelis constant), 454, 456 Krypton, 71 Kw (equilibrium constant), 296 L LacA, 490 LacI regulator gene, 490 Lac operon, 490 Lactaid, 417 Lactate, 232, 518 Lactic acid, 302, 342 Lactose, 402, 410–412, 415, 489–490, 512 Lactose intolerance, 417 Lactose permease, 490 LacY, 490 LacZ, 490 Lanthanide elements, 36 Lauric acid, 254, 530 Laws, scientific, Lawsone (dye), 333 LDLs, see Low density lipoproteins Leaving groups, 367 Le Châtelier’s principle, 293–294, 307, 331 Lecithin, see Phosphatidylcholine Length, measurement of, 7, Leucine (Leu), 434, 534 Leucine-enkephalin, 439 Leukotrienes, 272, 274, 347 Levorotatory isomers, 343 Lewis, Gilbert N., 69 Ligases, 483, 493 “Like dissolves like,” 215, 222 Limestone, 220 Linear metabolic pathways, 506 Linear molecular shape, 105, 106 Line-bond method, 77–78 Line-bond structures, 94–102 Lingual lipase, 239 Linoleic acid, 254, 255 Linolenic acid, 254, 255, 257 Lipase enzymes, 239, 512, 513 Lipid(s), 253–275 in cell membranes, 266–267 eicosanoids, 272–274 fatty acids, 254–258 glyceropholspolipids, 267–269 glycolipids, 268–270 membranes composed of, 275, 276 phospholipids, 267–270 steroids, 270–273 triglycerides, 259–264 waxes, 258–259 Lipid metabolism, 528–532 fatty acid anabolism, 532 fatty acid catabolism, 528–529 and ketone bodies, 531 Lipogenesis, 532 Lipoproteins, 271, 512 Liquid(s), 4–5, 161–166 Liquid helium, 19 Liquid nitrogen (N2), 19 Lister, Joseph, 187–188 Liter (unit), 7, Lithium, 39, 67–69, 76 Lithium bromide, 76 Liver, 519, 535 L notation, 400 Logarithms, 300 London, Fritz, 109 London forces, 109, 110, 222, 254–256, 324, 366, 445 Low blood pressure, 150 Low density lipoproteins (LDLs), 257, 271–272 Lowry, Thomas, 289 Luciferin, 70 Lufenuron, 340 Luminescence, 70 Lungs, 166, 167, 201 Lye, 298 Lysine (Lys), 435, 534 Lysozyme, 239 M M, see Molarity McGwire, Marc, 275 Macular degeneration, 92 Mad cow disease, 118 Magnesite, 220 Magnesium, 75 Magnesium hydrogencarbonate, 76 Magnetic Resonance Imaging (MRI), 19, 49 Major bases (nucleotides), 472 “Making weight,” 164 Malate, 523, 526, 534 Malate dehydrogenase, 523 Maltase, 449 Maltose, 410–412, 415 Malvidin, 322 Mammals, 295, 533–534 Mannose, 519 D-Mannose, 405 Manometer, 149 Markovnikov, Victor, 369 Markovnikov’s rule, 369 Mars Climate Orbiter, 17 Mass: critical, 50 measurement of, 6–7 in moles, 82 of subatomic particles, 28–29 supercritical, 50 weight vs., 15 I-7 Mass number, 32 Mass relationships, in chemical reactions, 191–194 Matrix (mitochondria), 511 Matter, 4–5, 28 Measurement(s): accuracy of, 11 conversion of, 15–18 precision of, 11 significant figures in, 12, 14–15 units of, 6–8 Medical imaging, 2, 49 Medicine: proteins in, 459–460 radioisotopes in, 43–48 Mega- (prefix), 10 Melanin, 124 Melting points, of monosaccharides, 398 Membrane(s), 275–277 cell, 266–267 mitochondria, 511 movement across, 276–277 semipermeable, 240–241 Mental confusion, 423 Menthol, 362 Mercury (element), 38, 61, 148 in dental fillings, 80–81 in manometers, 149 and measurement of atmospheric pressure, 147–148 in seafood, 257–258 in thermometers, 19, 162 Messenger RNA (mRNA), 485–486 and genetic code, 486–487 and translation, 487–488 Metabolic pathways, 457, 506–507 Metabolism, 506–535 amino acid, 532–534 anabolism, 507, 510, 512, 532 and ATP yield from glucose, 526 catabolism, 507, 510–511, 528–529 and citric acid cycle, 522–524 compounds important to, 508–509 defined, 507 digestion, 512–514 and electron transport chain, 524–527 fatty acid anabolism, 532 fatty acid catabolism, 528–529 gluconeogenesis, 519–521 glycogen in, 521–522 glycolysis, 514–519 ketone bodies, 531 lipid, 528–532 and metabolic pathways, 506–507 and oxidation/reduction reactions, 378 and oxidative phosphorylation, 524–527 pyruvate in, 518 Metabolizing ethanol, 376 Metals, 34 I-8 INDEX Metallic crystalline solids, 167–168 Metalloids (semimetals), 34 Meta (m) position of substituents, 324–325 Meter (unit), 7, Methamphetamine, 346 Methanal (formaldehyde), 373, 374, 377 Methane, 111, 112, 184–185, 323 Methanethiol (methyl mercaptan), 364, 365 Methanoic acid (formic acid), 125, 323–324 Methanol (methyl alcohol, CH3OH), 125, 364, 365, 367, 377, 471 Methedrine, 346 Methionine (Met), 363, 434, 486, 534 Methyl alcohol, see Methanol Methylamine, 303, 334, 336 Methylammonium ion, 302, 303, 336 Methylbenzene (toluene), 122 Methyl bromide, 367 3-Methyl-1-butanethiol, 362 2-Methylbutanoate ion, 327 2-Methylbutanoic acid, 327 3-Methylbutanoic acid, 323 2-Methyl-2-butanol, 369 3-Methyl-2-butanol, 369 2-Methyl-2-butene, 123, 369 Methyl butyl ketone (2-hexanone), 374 Methyl chloride, 367 1-Methylcyclohexanol, 369 2-Methylcyclohexanol, 369 Methylcyclohexene, 369 Methylcyclopentane, 119 2-Methylcyclopentanol, 372 1-Methylcyclopentene, 372 3-Methylcyclopentene, 372 Methylene chloride, 106 N-Methylethanamine (ethylmethylamine), 336 2-Methyl-3-heptanone (butyl isopropyl ketone), 373 2-Methylhexane, 116 3-Methylhexane, 114 Methyl mercaptan (methanethiol), 364, 365 2-Methyl-4-octene, 122 2-Methylpentane, 115 3-Methylpentane, 115 4-Methyl-1-pentane, 122 3-Methyl-2-pentanol, 372 2-Methyl-1-pentene, 372 2-Methyl-2-pentene, 372 4-Methylphenol, 328 2-Methylpropanal, 373 N-Methyl-1-propanamine (methylpropylamine), 334 2-Methylpropane, 115 2-Methyl-2-propanol (t-butyl alcohol), 364 Methylpropylamine (N-methyl-1propanamine), 334 Methyl propyl ketone, see 2-Pentanone Methylsulfonylmethane (MSM), 383 Metric system, 6–7, 10 Micelles, 226 Michaelis-Menten enzymes, 453–454, 457 Micro- (prefix), 10 Microfibrils, 447 Milk, 298 Milk of magnesia, 238 Milli- (prefix), 10 Minor bases (nucleotides), 472 Mitochondria, 511, 512, 518, 522–525, 527 Mixtures, 214 Mixtures (racemic), 343 Moderator (nuclear reactor), 51 Molarity (M), 231–235 Moles, 37–38 and formula weight, 82 and mass, 39 and volume, 155–156 Molecular crystalline solids, 167–168 Molecular formula: defined, 78 drawing structural formula from, 94 Molecular shapes, 104–106 Molecular weight, 83 Molecule(s), 78–80 binary, 79–80 diatomic, 78 native, 443 polar, 106–107 saturated, 187 unsaturated, 187 Mole relationships, in chemical reactions, 191–194 Monoacylglycerides, 512–514 Monoatomic anions, 62, 71–72 Monoatomic cations, 62 Monoatomic ions, 62, 63, 75 Monolayer, 226 Monosaccharides, 398–409, 471, 512, 513 classification of, 399 cyclic form of, 406–409 defined, 398 derivatives of, 402–404 mutarotation of, 408–409 in oligosaccharides, 410–412 reactions of, 404–406 stereoisomers in, 400–401 Monunsaturated fatty acids, 254–256 Mordant red, 333 Mouth, 512, 513 MPTP, 355 MRI, see Magnetic Resonance Imaging mRNA, see Messenger RNA MSM (methylsulfonylmethane), 383 mtDNA, mitochondrial, 512 Mumps, 489 Muriatic acid, 288 See also Hydrochloric acid Muscalure, 121 Muscarine iodide, 337 Muscles, intercostal, 166, 167 Muscle tissues, 295 Mutagens, 492 Mutarotation, 408–409 Mutation, 491–492 Myocardial infarction, 233 Myoglobin, 295 Myristic acid, 254 N NADϩ, see Nicotinamide adenine dinucleotide NADH, see Nicotinamide adenine dinucleotide, reduced form NADPϩ (nicotinamide adenine dinucleotide phosphate), 510 NADPH (nicotinamide adenine dinucleotide phosphate, reduced form), 401–402 Naming rules, see IUPAC naming rules Nandrolone laurate, 275 Nano- (prefix), 10 Naphthalene, 112 NASA, 17 National Heart, Lung and Blood Institute, 150 Native molecules, 443 Natural sweeteners, 415 Negative effectors, 457, 517 Negatively charged ions, 64 Neon, 71 Net ionic equations, 218 Neutral atoms, 69 Neutralization, 303–304 Neutral solutions, 297, 298 Neutrons, 28–29, 33–34, 62 Newton, Isaac, Ni2ϩ, 452 Niacin, 452 Nickel chloride, 76 Nicotinamide adenine dinucleotide (NADϩ), 371, 402, 508–510, 518–520, 526, 528, 529 Nicotinamide adenine dinucleotide, reduced form (NADH), 371, 377, 452, 508, 509, 514, 518–520, 525, 526, 528, 529 Nicotinamide adenine dinucleotide phosphate (NADPϩ), 510 Nicotinamide adenine dinucleotide phosphate, reduced form (NADPH), 401–402 Nicotine, 322 Nitrates, 217 Nitrate ion, 65, 76, 97, 98, 303 Nitric acid, 288, 303 Nitric oxide, 180, 181 Nitrite ion, 65 Nitrogen, 61, 71 excretion of, 533–534 liquid, 19 Nitrogen dioxide, 181 Nitrogen gas, 79, 179, 180 Nitrous oxide, 148, 179, 180 Nobel Prize, 128 Noncompetitive inhibition, 456 Noncompetitive inhibitors/inhibition, 454–456 Noncovalent bonds, 448 Noncovalent interactions, 108–110, 140 defined, 108 and permanent charges, 108–109 and tertiary structure, 444–445 Nonmetals, 34 Nonoses, 399 Nonpolar amino acids, 434, 436–437 Nonspontaneous processes, 143–146 Nonspontaneous reactions, 451 Nonsteroidal anti-imflammatory drugs (NSAIDs), 272 Norepinephrine, 367–368 Nose, runny, 347 Novocain, 189 NSAIDs (nonsteroidal antiimflammatory drugs), 272 N-terminus, 438 Nuciferine, 362 Nuclear change, 40 Nuclear equations, 41 Nuclear radiation, 40–45 Nuclear reactors, 51–52 Nuclei, see Nucleus Nucleic acid(s), 469–496 See also Deoxyribonucleic acid (DNA); Ribonucleic acid (RNA) and control of gene expression, 489–490 denaturation of, 480–481 and information flow, 481 monosaccharides as building block of, 471 and mutation, 491–492 nucleosides in, 472–473 nucleotides in, 470, 474 organic bases as building block of, 472 phosphoric acid as building block of, 470 polynucleotides in, 476–477 primary structure, 478 and recombinant DNA, 492–494 secondary structure, 478 tertiary structure, 479–480 Nucleophiles, 367 Nucleophilic substitution reactions, 367–368 Nucleosides, 472–473 Nucleoside diphosphate, 475 Nucleoside triphosphate, 475 INDEX Nucleosomes, 480 Nucleotides, 470, 474 cyclic, 475 drawing, 474 and monosaccharide, 471 and organic bases, 472 polynucleotides, 476–477 Nucleotide residues, 476, 478 Nucleus (nuclei), 28–29, 32, 40, 62 Numbers: exact, 12 rounded, 14–15 significant, 12 Nutrasweet, 176, 177, 417 O Observations, 2–3 Octanoic acid, 224, 324 Octet rule, 71–72, 77 Octoses, 399 Octyl methoxycinnamate, 124 Oleic acid, 254, 255 Olestra, 266 Oligonucleotides, 476 Oligopeptides, 437–438, 513 Oligosaccharides, 410–414, 417, 512, 513 defined, 398 disaccharides, 410–412 glycosidic bonds, 410–412 indigestible, 417 Omega-3 fatty acids, 257–258 Operons, 490 Oral temperature, 16 Orbitals, 66 Organic bases (amines), 472 Organic compounds, 93–129, 222–224 alcohols, 125–127 alkanes, 110–114 alkenes, 121–122 alkynes, 121–122 aromatic, 122 carboxylic acids, 125–127 conformations, 117–118 constitutional isomers, 115–117 cycloalkanes, 118–120 esters, 125–127 and formal charge, 94–102 hydrocarbons, 110–114 and structural formulas, 94–102 Organ transplants, 422 Origin (DNA replication), 482 Ortho (o) position of substituents, 324–325 Orthostatic hypotension (low blood pressure), 150 Osmosis, 240–241 Osmotic pressure, 241 Outer membrane (mitochondria), 511, 525 Ovarian cancer, 492 Oxaloacetate, 520, 522, 523, 526, 531, 533, 534 Oxandrolone, 275 Oxidation/oxidation reactions, 183–188, 202, 262–263, 370–372 of alcohols, 371 of aldehydes, 374–375 and antiseptics, 187–188 and combustion, 183–187 and hydrogenation, 187–188 of monosaccharides, 405 of phenols, 332 rules for identifying, 185 of thiols, 371 Oxidative deamination, 533 Oxidative phosphorylation, 510–512, 524–527, 535 Oxidized (term), 183 Oxidizing agent(s): benzol peroxide, 188 defined, 183 iodine, 188 potassium dichromate, 332 Oximeter (pulse), 169 Oxy-10 (acne medication), 188 Oxygen, 33, 61, 71, 295 in blood, at high altitudes, 138 and hyperbaric treatments, 222 Oxygen-18, 42–43 Oxygen gas, 79, 179, 180 Oxyhemoglobin, 169 Oxymyoglobin (MbO2), 295 Oxytocin, 439 P PAHs, see Polycyclic aromatic hydrocarbons Palmitic acid, 227, 254, 327, 532 Palmitic ion, 327 Palmitoleic acid, 254 Pancreatitis, 458 Pantothenic acid, 452 Paprika, 325 Parallel sheets, 442, 443 Para (p) position of substituents, 324–325 Parent chain(s): of amines, 333–334 of carbon atoms, 112 of carboxylic acids, 323 Partial hydrogenation, 261–262 Partial negative charge, 106, 108 Partial positive charge, 106, 108, 185 Partial pressure, 158–161, 166 Particles: high-energy, 40 subatomic, 28–29 Parts per thousand/million/billion, 230 PCR, see Polymerase chain reaction Peanut allergy, 432, 460 Pectin, 496 Pentane, 111, 112, 222, 223, 365 Pentanoic acid, 125, 324 1-Pentanol (pentyl alcohol), 125, 365 2-Pentanone (methyl propyl ketone), 373–374 Pentapeptides, 438, 439 cis-2-Pentene, 123 trans-2-Pentene, 123 Pentoses, 398, 399 Pentose phosphate pathway, 519 Pentyl alcohol, see 1-Pentanol 1-Pentyne, 112 Pepper, chili, 325 Pepsin, 452, 513 Peptides, 437–438, 440–441 Peptide bonds, 437–438, 458–459 Pepto Bismol, 238 Percent yield, 197 Period (elements), 36 Periodic table, 34–35, 68–69, 148 Permease, 490 Peroxidase, 452 PET imaging, see Positron emission tomagraphy Petroleum, 117 PGU (polygalacturonase), 496 pH (pH scale), 297–299 and amino acids, 436 of blood serum, 308–311 and carboxylic acid, 326 and conjugate acids of amines, 336 defined, 297 effect of, on acid and conjugate base concentrations, 305–306 effect of, on enzymes, 452, 453 and fatty acids, 327 and peptide structure, 440–441 Phagocytosis, 378 Phases of matter and energy, 140 Phenanthrene, 122 Phenol(s), 324–329 capsaicin, 325 catechin as, 235, 324 conjugate base of, 328 defined, 322 gentisic acid (anti-rheumatism drug), 235, 324 hydrogen bonds in, 325l oxidation of, 332 physical properties of selected, 326 and pKa , 327 and strong bases, 328 urushiol as, 235, 324 as weak organic acids, 326–328 Phenolphthalein, 304 Phenoxide ion, 327 Phenylalanine (Phe), 176, 177, 202, 225, 434, 492, 534 Phenylalanine hydroxylase, 202 Phenylketonuria (PKU), 202 Phenylketonurics, 176, 177, 202 Phenylpropanolamine, 346 pH meter, 299 pH optimum, 452 Phosphates, 217 Phosphate esters, 470 Phosphate ion (PO4 3Ϫ), 65, 303, 470 I-9 Phosphate monoesters, 471, 474, 476 Phosphatidylcholine (lecithin), 267–268 Phosphatidylethanolamine (cephalin), 267–268 Phosphatidylserine, 267–268 Phosphoanhydride bonds, 475 Phosphodiester bonds, 475 Phosphoenolpyruvate, 516, 520, 522, 528, 531 Phosphoester bonds, 474, 483 Phosphofructokinase, 515, 517 Phosphoglucose isomerase, 515 Phosphoglycerate, 519, 520 2-Phosphoglycerate, 516, 519, 520, 522, 528 3-Phosphoglycerate, 516, 519, 520, 522, 528 Phosphoglycerate kinase, 516 Phosphoglycerate mutase, 516 Phosphoglycomutase, 522 Phospholipids, 267–270 Phosphoric acid (H3PO4), 302, 303, 470 Phosphorus, 71 Phosphorylation, 457–458, 510–512 Physical change, 5, 40, 140 Physical properties, Physiological pH, 452 pI (isoelectric point), 436 pKa , 302 PKU (phenylketonuria), 202 Plane-polarized light, 343–344 Plants, as pH indicators, 301 Plasma, blood, 201 Plasmids, 479, 493 Plutonium-239, 45, 51, 52 Pneumonia, 489 Poison ivy/poison oak, 235, 324 Polar-acidic amino acids, 435–437, 445 Polar-basic amino acids, 435–437, 445 Polar covalent bonds, 103–107 and electronegativity, 103–107 and polarity, 106–107 and shape, 104–106 Polar molecules, 106–107 Polar-neutral amino acids, 435–437, 445 Polio, 489 Pollen, 320 Polonium-214, 45 Polonium-218, 45, 46 Polyatomic ions, 64–65, 97–98 and covalent bonds, 97–98 in ionic compounds, 75–76 structural formulas, 97–98 Polycyclic aromatic hydrocarbons (PAHs), 122 Polygalacturonase (PGU), 496 Polyhydroxy aldehydes, 398 Polymerase chain reaction (PCR), 452–453, 494–495 Polynucleotides, 476–477 Polypeptides, 437–438, 442, 513 I-10 INDEX Polypeptide chain, 438 Polysaccharides, 418–421, 512, 513 defined, 398 heteropolysaccharides, 481 homopolysaccharides, 418–420 Polyunsaturated fatty acids, 254–258 p orbitals, 66 Positive effectors, 457, 517 Positively charged ions, 62 Positrons, 42–44 Positron emission tomagraphy (PET), 42, 53–54, 198 Positron radiation, 42 Post-transcriptional modifications, 486 Post-translational modifications, 489 Potassium, 67, 68, 73, 179 Potassium dichromate (K2Cr2O7), 332, 370 Potassium hydroxide, 288 Potassium sorbate, 328 Potential energy, 5–6 Pound (unit), 6–8 Precipitate, 214, 220 Precipitation reactions, 218–219 Precision (measurement), 11 Preservatives, 328 Pressure, 146 atmospheric, 146–149, 160–161, 165 blood, 149, 150 diastolic, 150 of a gas, 146 osmotic, 241 partial, 158–161, 166 standard temperature and, 148 systolic, 150 and temperature, 152–153 and tire inflation, 152 total, 158–159 vapor, 165 and volume, 151 Primary (1°) alcohol, 364, 370 Primary (1°) amine, 333–336 Primary structure (DNA), 478 Primary structure (proteins), 441–442 Prions, 118 Procaine, 190 Prodrugs, 227–228 Products (of chemical reactions), 178–179, 290–292, 294 Product atoms, 184–185 Progesterone, 272, 273, 363 Proline (Pro), 434, 447 Promoter sites, 484 Proofreading (DNA replication), 483 Propanal, 374 1-Propanamine (propylamine), 335, 336 Propane, 101, 111, 112, 365 Propanoate ion, 327 Propanoic acid, 125, 324, 327 1-Propanol, see Propyl alcohol 2-Propanol, see Isopropyl alcohol Propanone (dimethyl ketone, acetone), 331, 373, 374, 531 Propene, 112, 369 Properties: chemical, 74 physical, Propranolol, 344 Propyl alcohol (1-propanol), 125, 364, 365, 367, 369 Propylamine, see 1-Propanamine Propyl iodide, 367 Prostaglandins, 272, 347, 454, 460 Prostate cancer, 492 Prosthetic groups, 445 Protease enzymes, 513 Protective enzymes, 378 Protein(s), 225, 276 as catalysts, 449–453 defined, 438 denaturation of, 449 digestion of, 513–514 fibrous, 441, 447 and genes, 477 globular, 441, 448 in medicine, 459–460 and post-translational modification, 494 primary structure of, 441–442 quaternary structure of, 446 secondary structure of, 442 simple vs complex, 445 synthesis (translation) of, 487–488 tertiary structure of, 443–445 total, 232 Protofibrils, 447 Protons, 28–29, 33, 62–64 Pure elements, 61 Pure substances, 214 Purines, 242–243, 335, 472 Purine rings, 335 Purple cabbage, 301 Putrescine, 336 Pyramidal molecular shape, 105, 106 Pyranoses, 406, 407 Pyridine, 335 Pyrimidines, 335, 472 Pyrophosphate (PPi), 510 Pyruvate, 514, 516, 518–520, 522, 527, 532–534 Pyruvate decarboxylase, 331 Pyruvate dehydrogenase complex, 518 Pyruvate kinase, 516, 517 Pyruvic acid, 331, 514 Q Quantum mechanics, 66–67 Quart (unit), 7, Quaternary (4°) ammonium ions, 333–336 Quaternary structure (proteins), 446 Quinones, 332–333, 370 R Racemic mixtures, 343 Radiation: background, 44 common forms of, 42–43 cosmic, 44 effects of, 44 electromagnetic, 43, 124 forms of, 42–43 long-term exposure to, 44 nuclear, 40–45 positron, 42 UV, 124 Radiation therapy, 47–48 Radioactive decay, 42, 45–46 Radioactive isotopes (radioisotopes), 40–43 for diagnosis and therapy, 47–48 half-life of, 45–46 in medicine, 43–48 and radiation, 40–43 Radium, 69 Radium-226, 40 Radon, 71 Radon-222, 45 Raffinose, 412–413, 417 Rainwater, 298 Rate of reaction, see Reaction rate RDAs (Recommended Dietary Allowances), 31 Reactants, 178–179 and equilibrium, 290–292, 294 limiting, 195–197 Reactant atoms, 184–185 Reaction(s) (chemical reactions), 178–181 activation energy for, 451 calculating yield of, 195–197 combustion, 184–186 coupled, 506 dehydration, 190 free energy in, 198–200 in fuel cells, 178 gas producing, 219–220 hydration, 189–190 hydrogenation, 187–188 hydrolysis, 189 limiting reactant in, 195–197 mole and mass relationships in, 191–194 of monosaccharides, 404–406 nonspontaneous, 451 oxidation/reduction, 183–188 precipitation, 218–219 rate of, 451 and reaction rate, 198–200 spontaneous, 451 types of, 182–183 water in, 189–191 Reaction energy diagrams, 198 Reaction rate, 198–200 and catalysts, 198–200 defined, 198–199 forward/reverse, 294 and temperature, 199 Receptors, smell and taste, 128 Recombinant DNA, 492–494 Recommended Dietary Allowances (RDAs), 31 Rectal temperature, 16 Red blood cells, 221, 422 Reduced (term), 183 Reducing agents, 183 Reducing sugars, 405 Reduction, 183–184, 261, 405 Relative specificity, 450 Remote temperature sensing, 16 Renaturation, 480, 481 Replication: DNA, 481–483 semiconservative, 482 Replication fork, 483 Representative elements, 36, 69 Reprocessed nuclear fuel, 51–52 Residues, 258 Resorcinol, 326 Respiration, 166–167 Retina, 129 11-cis-Retinal, 129 all-trans-Retinal, 129 Retroviruses, 489 Reverse trancriptase, 489 Reverse transcription, 481 Reversible inhibitors, 454 Reversible reaction, 290–292 L-Rhamnose, 403 Rhodopsin, 129 Ribitol, 403 Riboflavin (B2), 452 ␣-D-Ribofuranose, 408 ␤-Ribofuranose, 471 ␤-D-Ribofuranose, 408 Ribonucleic acid (RNA), 402, 469, 477, 481, 484–487 and genetic code, 486 and post-transcriptional modification, 494 as single strand, 484 and transcription, 484–485 types of, 485–486 Ribonucleosides, 472, 473 Ribonucleotides, 474 Ribose, 471 D-Ribose, 401–403, 408 Ribosomal RNAs, 486 Ribosomes, 486 Rings: aromatic, 122, 322 benzene, 112, 121–122 five-membered, in monosaccharides, 407 purine, 335 six-membered, in monosaccharides, 406–409 RNA, see Ribonucleic acid RNA interference (RNAi), 491 RNA polymerase, 484, 490 RNA viruses, 489 Rods (retina), 129 Roentgen, Wilhelm, Rotenone, 504, 505 Rough endoplasmic reticulum, 511 Rounded numbers, 14–15 Rubbing alcohol, see Isopropyl alcohol INDEX Rubidium, 70 Rubidium-84, 46 S Saccharides, 398 Saccharin, 415, 417 S-Adenosylmethionine, 367–368 Saliva, 239 Salivary amylase, 512, 513 Salts, bile, 272, 273 Salt bridges, 109 in hemoglobin, 448 and tertiary structure, 444, 445 Saponification, 263–264 SARS (severe acute respiratory syndrome), 16 Saturated fatty acids, 254–256 Saturated hydrocarbons, 120 Saturated molecules, 187 Saturated solutions, 228 Saturated triglycerides, 261 Scale, 220 Schrödinger, Erwin, 66 Scientific laws, Scientific method, 2–3 Scientific notation, 9–11 Scrapie, 118 Scurvy, 447 Seafood, omega-3 fatty acids in, 257–258 Seals, 295 Secondary (2°) alcohol, 364, 370 Secondary (2°) amine, 333–336 Secondary structure (DNA), 478 Secondary structure (proteins), 442 Semiconservative replication, 482 Semimetals (metalloids), 34 Semipermeable membrane, 240–241 Sepsis, 187 Serine (Ser), 435, 438, 454, 457 Severe acute respiratory syndrome (SARS), 16 Sewage treatment plants, drugs in, 382 Sex hormones, 272, 273 Shell, valence, 68 Shielding (from radiation), 44–45 Shivering, 527 Shock, 460 Short tandem repeats (STRs), 494–496 Sickle cell anemia, 492 Siderite, 220 Significant figures, 12, 14–15, 300 Significant numbers, 12 Silicon, 35, 36, 69 Silicon tetrachloride, 79 Silver, 36 Silver nitrate, aqueous, 214 Simple proteins, 445 Simple sugars, 225 Single bonds, 78–79 Single replacement reactions, 182 Single-strand binding proteins (SSBs), 482, 483 SI units, 6–7 Six-membered rings, 406–409 Small intestine, 512, 513 Smallpox, 489 Smell receptors, 128 Soaps, 226, 298 Sodium, 38, 68, 71, 72, 74 Sodium benzoate, 328 Sodium bicarbonate (NaHCO3), 219 Sodium chloride, 74–75, 214 Sodium cyclamate, 415, 417 Sodium fluoride, 85 Sodium hydroxide, 288 Sodium ion (Naϩ), 232 Sodium 4-methylphenoxide, 328 Sodium propanoate, 328 Sodium sulfate, 76 Sodium sulfide (Na2S), 219 Sodium sulfite, 75 Sodium thiosulfate, 184 Soft drinks, 298 Solids, 4–5, 167–168 Solubility, 215, 216 of amines, 336 of amphipathic compounds, 226 of biochemical compounds, 224–227 of fatty acids, 254, 256 of gases in water, 221 and hydrogen bonding, 223 of hydrophilic compounds, 224–225 of hydrophobic compounds, 225 of ions in water, 216–217 and London forces, 222 and temperature, 215 Soluble compounds, 215 Solutes, 214 Solutions, 214–241 acidic, 297–298 basic, 297–298 concentration of, 228–235 dilution of, 236 gas producing reactions in, 219–220 hypertonic, 240, 241 hypotonic, 240, 241 isotonic, 240, 241 neutral, 297–298 of organic compounds, 222–224 precipitation reactions in, 218–219 reactions of ions in aqueous, 216–220 saturated, 228 unsaturated, 228 Solvents, 214 Somatostatin, 438 s orbitals, 66 Sorbitol, 403, 405, 415, 417 Spearmint, 343, 344 Specific gravity, 163–164 Specific heat, 142 Specificity (of enzymes), 450–451 Spectator ions, 218 SPF factor, 124 Sphingolipids, 268, 269, 276, 528 Sphingosine, 268–269, 414 Sphygmomanometer, 149–150 Spiral metabolic pathways, 506 Splenda, 417 Spontaneous processes, 143–146 Spontaneous reactions, 451, 506 Squid, 70 Stability, 71 Stachyose, 412–413, 417 Standard temperature and pressure (STP), 148 Starch, 419–420, 512, 513 Stargardt’s disease, 93, 129 Starvation, 331 States of matter and energy, 140 Steam, 140 Stearic acid, 254–255, 322, 414 Stereoisomer(s), 118–119, 265, 341–345, 437 of aldohexoses, 401 in carbohydrates, 400–401 cis, 123 effect of chiral carbon atoms on, 345 in monosaccharides, 400–401 plane-polarized light, 343–344 trans, 123 Stereospecificity, 451 Steroids, 270–273 anabolic, 275 and bile salts, 272, 273 defined, 270 Steroid hormones, 272, 273, 275 Stethoscope, 150 Stomach, 423, 512, 513 STP (standard temperature and pressure), 134 Streptomyces, 73 Strong bases, 328 Strontium-90, 51 STRs, see Short tandem repeats Structural formulas, 94–102 condensed, 101 electron dot, 94, 104 line-bond, 94–102, 104 skeletal, 101–102, 104 Subatomic particles, 28–29 See also Electrons alpha particles, 40–41 beta particles, 40–42 charge of, 28 mass of, 28 neutrons, 28–29 positrons, 42 protons, 28–29 Sublimation, 141 Substances, pure, 214 Substituents (atoms), 112, 324–325 Substrates, 449, 451 Succinate, 523, 534 Succinate dehydrogenase, 523 Succinyl-CoA, 523, 534 Succinyl-CoA synthetase, 523 Sucralose, 416, 417 Sucrase, 512 I-11 Sucrose (table sugar), 410–412, 415, 416, 512 Sugar(s): alcohol, 403–404 amino, 403 carboxylic acid, 404 cellobiose, 410–412 D, 400–402 deoxy, 402–403 invert, 415, 416 L, 400–402 lactose, 410–412 maltose, 410–412 reducing, 405 and saccharides, 398 simple, 225 sucrose, 410–412 Sugar-phosphate backbone, 476–479, 493 Sulfanilamide, 454, 456 Sulfates, 217 Sulfate ion, 65, 97, 98, 303 Sulfides, 363 boiling points of, 366 oxidation of, 371 physical properties of, 365 preparation of, 367 structure of, 362 Sulfite ion, 65 Sulfoxides, 371 Sulfur, 33, 36 Sulfur dioxide, 79 Sulfuric acid, 288, 303 Sulfur trioxide, 79, 83 Sunette, 417 Sunscreens, 124 Supercoiling, 479 Supercritical mass, 50 Superoxide dismutase, 525 Superoxide ion (O2 Ϫ), 378 Suspensions, 238 Sweeteners: artificial, 415–416 for diabetics, 417 natural, 415 Sweetness: and monosaccharides, 398 relative, 415–417 Sweet’ N Low, 417 Synthesis reactions, 182 Synthetase enzymes, 487 Synthetic heroin, 355 Systolic pressure, 150 T Table sugar, see Sucrose Taste, 288 Taste receptors, 128 Temperature(s): conversions involving, 19 and denaturation, 449 and density, 163–164 effect of, on enzymes, 452–453 measurement of, 7–8 and pressure, 152–153 and rate of reaction, 451 and solubility, 215 and specific gravity, 163–164 I-12 INDEX Temperature(s) (cont.) and thermodynamic changes, 144–145 and viscosity, 161–162 and volume, 154 Temperature optimum (of an enzyme), 452 Template strand, 484–485 Temporal artery thermometers, 16 Termination (protein translation), 487, 488 Termination sequence, 485 Tertiary (3°) alcohol, 364, 370 Tertiary (3°) amine, 333, 334, 336 Tertiary structure (DNA), 479–480 Tertiary structure (proteins), 443–445 and covalent interactions, 445 and noncovalent interactions, 444–445 Testosterone, 232, 272, 273, 275, 363 Tetanus, 222 Tetraethylammonium ion, 334 Tetrahedral atom arrangement, 168 Tetrahedral molecular shape, 106 Tetrahydrogestrinone (THG), 252, 277 Tetramers, 448 Tetrapeptides, 437 Tetroses, 398, 399 TH01, 494 Theoretical yield, 196–197 Theories, 2–3 Thermometers, 16, 162 THG, see Tetrahydrogestrinone Thiols, 362–363 boiling points of, 366 oxidation of, 371 physical properties of, 365 preparation of, 367 structure of, 362 Thiol groups ( ¬ SH), 445 Thoracic cavity, 166, 167 Thorium-230, 42 3Ј-terminus, 476, 477 Threonine (Thr), 435, 457, 534 Thromboxanes, 272 Thymidine 5Ј-monophosphate (dTMP), 474 Thymine (T), 335, 472, 474, 476 Thyroid cancer, 47 Thyroid scan, 47 Thyrotropin, 438 Thyrotropin-releasing factor, 438 Tire pressure, 152 Tissue, 481 Titin, 439 Titration, 304–305 Tolerable Upper Intake Level (UL), 31, 32 Toluene (methylbenzene), 122 Tomography, 49 Tooth enamel, 84 Topoisomerases, 479 Torr (unit), 147–148 Torricelli, Evangelista, 147–148 Total protein, 232 Transacetylase, 490 Transaminase enzymes, 532 Transamination, 532–533 Transcription, 481, 484–485 reverse, 481 and termination sequence, 485 Trans fats, 265 Transfer RNA (tRNA), 485 and translation, 487–488 Trans isomers, 120, 123 Transition elements, 36 Transition metals, 72 Translation (protein synthesis), 487–488 defined, 481 elongation, 487–488 initiation, 487, 488 and post-translational modification, 489 termination, 487, 488 Transport, active, 276–277, 525 Transport proteins, 448 Trenbolone, 277 Triethylamine, see N,NDiethylethanamine Triglycerides, 259–264, 512 catabolism of, 528–529 digestion of, 512–514 important reactions of, 261–262 and oxidation, 262–263 and reduction, 261 and saponification, 263–264 Trigonal molecular shape, 105, 106 Triose phosphate isomerase, 516 Trioses, 398, 399 Tripeptides, 437–438 Triple bonds, 78–79 Triple helix, 447 Triplet code, 486 tRNA, see Transfer RNA Troponin I, 233 Trypsin, 458–460, 513 Trypsin inhibitor, 460 Trypsinogen, 458, 459 Tryptophan (Trp), 434, 534 Tuberculosis, 344 Tympanic membrane thermometers, 16 Tyrosine (Tyr), 202, 435, 457 U UDP-glucose phosphorylase, 522 UL, see Tolerable Upper Intake Level Ultraviolet (UV) light, 65 Ultraviolet (UV) radiation, 124 UMP (uridine 5Ј-monophosphate), 474 Unit conversions, 15, 17–18 Units of measurement, 6–8 conversions, 15, 17–18 metric prefixes, 10 parts per, 230 percentages, 229 Unsaturated fatty acids, 255–256 Unsaturated hydrocarbons, 120 Unsaturated molecules, 187 Unsaturated solutions, 228 Uracil (U), 472, 474, 477 Uranium-235, 50, 51 Uranium-238, 45, 50 Urea cycle, 533 Urease, 450, 452 Uric acid, 243, 534 Uridine, 473 Uridine 5Ј-monophosphate (UMP), 474 Uridine 5Ј-triphosphate (UTP), 508, 510, 521 Uridinyl, 508 Urine, 16, 163, 242, 243, 298, 375 Urushiol, 324, 325 U.S Anti-Doping Agency, 252 U.S Food and Drug Administration (FDA), 257, 265, 266, 382 UTP, see Uridine 5Ј-triphosphate UV, see under Ultraviolet Viscosity, 161–162 Visible light, 65 Vitamin B12 , 232 Vitamin C deficiency, 447 Vitreous humor, 481 VLDLs (very low density lipoproteins), 271 Volume: measurement of, 7–8 and moles, 155–156 and pressure, 151 and temperature, 154 Volume/volume percent, 229 W Water, 298, 303 and acetal reactions, 380 boiling point of, 140–141 and chemical reactions, 189–191 freezing point of, 140–141 hard, 220 ionization of, 296–297 phase changes, 144–145 phases of, 140–142 solubility of gases in, 221 specific heat of, 142 vapor pressure of, 165–166 Water insolubility, 253 Waxes, 258–259 Weight: formula, 81–82 mass vs., 15 molecular, 83 Weight reduction, rapid, 164 Weight/volume percent, 229 Weight/weight percent, 229 Whales, 295 Work, V Valence electrons, 68, 69, 71–72, 77 Valence shell, 68 Valine (Val), 225, 434, 492, 534 Valinomycin, 73 Vanillin, 363 Vaporization, heat of, 140, 142, 143 Vapor pressure, 165–166 Vegetable oils, partially hydrogenated, 263 Velocity, maximum, 454, 456 Verbascose (pentasaccharide), 412–413, 417 Very low density lipoproteins (VLDSs), 271 Vinegar, 287, 298, 323 Vioxx, 273 Viral DNA, 489 Viral RNA, 489 Viruses, 489 X Xanthine, 456 Xenon, 71 Xopenex, 358 X rays, 2, 47, 49 Xylitol, 415 ␣-D-Xylofuranose, 409 ␤-D-Xylofuranose, 409 Y Yeast, brewer’s, 331 Yeast tRNAPhe, 485 Yellowstone hot springs, 452, 453 Yield (of a reaction), 195–197 Ynamines, 333 Ynoic acids, 323 Z Zn2ϩ, 452 Zwitterion, 436 Zymogens, 458–459 T H E NAME Actinium Aluminum Americium Antimony Argon Arsenic Astatine Barium Berkelium Beryllium Bismuth Bohrium Boron Bromine Cadmium Calcium Californium Carbon Cerium Cesium Chlorine Chromium Cobalt 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 Lutetium Magnesium Manganese Meitnerium Mendelevium SYMBOL ATOMIC NUMBER Ac Al Am Sb Ar As At Ba Bk Be Bi Bh B Br Cd Ca Cf C Ce Cs Cl Cr Co 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 Lu Mg Mn Mt Md 89 13 95 51 18 33 85 56 97 83 107 35 48 20 98 58 55 17 24 27 29 96 110 105 66 99 68 63 100 87 64 31 32 79 72 108 67 49 53 77 26 36 57 103 82 71 12 25 109 101 ATOMIC WEIGHT (227) 26.98154 (243) 121.760 39.948 74.92160 (210) 137.327 (247) 9.012182 208.9804 (264) 10.811 79.904 112.411 40.078 (251) 12.0107 140.116 132.9054 35.453 51.9961 58.9332 63.546 (247) (281) (262) 162.50 (252) 167.259 151.964 (257) 18.99840 (223) 157.25 69.723 72.64 196.9665 178.49 (269) 4.00260 164.93032 1.00794 114.818 126.9045 192.217 55.845 83.80 138.9055 (262) 207.2 6.941 174.967 24.3050 54.93805 (268) (258) NAME 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 Ununbium2 Ununquadium2 Uranium Vanadium Xenon Ytterbium Yttrium Zinc Zirconium E L E M E N T S SYMBOL ATOMIC NUMBER 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 Uub Uuq U V Xe Yb Y Zn Zr 80 42 60 10 93 28 41 102 76 46 15 78 94 84 19 59 61 91 88 86 75 45 111 37 44 104 62 21 106 34 14 47 11 38 16 73 43 52 65 81 90 69 50 22 74 112 114 92 23 54 70 39 30 40 ATOMIC WEIGHT 200.59 95.94 144.24 20.1797 (237) 58.6934 92.9063 14.0067 (259) 190.23 15.9994 106.42 30.97376 195.078 (244) (209) 39.0983 140.90765 (145) 231.0359 (226) (222) 186.207 102.9055 (272) 85.4678 101.07 (261) 150.36 44.95591 (266) 78.96 28.0855 107.868 22.98977 87.62 32.065 180.9497 (98) 127.60 158.92534 204.383 232.0381 168.93421 118.710 47.867 183.84 (285) (289) 238.0289 50.9415 131.293 173.04 88.9058 65.39 91.224 For elements that not have stable isotopes, the mass number of the most stable isotope is given in parentheses Elements 112 and 114 have been discovered, but have not been given official names These elelments have been given temporary names, using the prefixes un (1), bi (2), and quad (4) P E R I O D I C Representative elements T A B L E O F E L E M E N T S 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 19 K Transition metals 8B 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 37 Rb 38 Sr 39 Y 40 Zr 41 Nb 42 Mo 43 Tc 44 Ru 85.4678 87.62 88.9058 91.224 92.9063 95.94 [98] 55 Cs 56 Ba 57 *La 72 Hf 73 Ta 74 W 75 Re 132.9054 137.327 2B 30 Zn 26.98154 28.0855 30.97376 32.065 35.453 39.948 28 Ni 1B 29 Cu 31 Ga 32 Ge 33 As 34 Se 35 Br 36 Kr 58.9332 58.6934 63.546 65.39 69.723 72.64 74.92160 78.96 79.904 83.80 45 Rh 46 Pd 47 Ag 48 Cd 49 In 50 Sn 51 Sb 52 Te 53 I 54 Xe 101.07 102.9055 106.42 107.868 112.411 114.818 118.710 121.760 127.60 126.9045 131.293 76 Os 77 Ir 78 Pt 79 Au 80 Hg 81 Tl 82 Pb 83 Bi 84 Po 85 At 86 Rn 204.383 207.2 [208.9804] [209] [210] [222] 69 Tm 70 Yb 71 Lu 138.9055 178.49 180.9479 183.84 186.207 190.23 192.217 195.078 196.9665 200.59 87 Fr 88 Ra 89 †Ac 104 Rf 105 Db 106 Sg 107 Bh 108 Hs 109 Mt 110 Ds 111 Rg 112 Uub 114 Uuq [223] [226] [227] [261] [262] [266] [264] [269] [268] [281] [272] [285] [289] 58 Ce 59 Pr 60 Nd 61 Pm 62 Sm 63 Eu 64 Gd 65 Tb 66 Dy 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 series 140.116 140.90765 90 Th 91 Pa 232.0381 231.0359 238.0289 67 Ho 68 Er 164.93032 167.259 168.93421 For elements that not have stable isotopes, the mass of the most stable isotope is given in parentheses Elements 112 and 114 have been discovered but have not been given official names The production of elements 113, 115, 116, and 118 has been reported, but at the time of this writing the experiments have not been reproduced by other researchers Q U I C K R E F E R E N C E G U I D E IONS AND IONIC COMPOUNDS ACIDS AND BASES − Acid (HA) and conjugate base (A ) concentrations, as a function of pH, Table 9.6 Interpreting equilibrium constants (Keq), Table 9.2 Ka and pKa values for selected acids, Table 9.4 Some common acids and bases, Table 9.1 pH values of some common solutions, Table 9.3 Relative strengths of some acids and their conjugate bases, Table 9.5 Common polyatomic ions, Table 3.2 Some transition metal ions, Table 3.1 The uses of some ionic compounds, Table 3.5 AMINO ACIDS, PROTEINS, AND ENZYMES MATH α-Amino acids present in proteins, Table 13.1 Amino acids that are essential for humans, Table 15.1 Enzyme cofactors, Table 13.2 ATOMS Subatomic particles, Table 2.1 The ground state electron distribution for the first 20 elements, Table 3.4 BONDING Bond types, Table 4.1 LIPIDS Common fatty acids, Table 8.1 Key esters found in some waxes, Table 8.2 Conversion factors and the factor label method, Section 1.6 Logs and antilogs, Chapter Math Support Measurements and significant figures, Section 1.5 Scientific notation and metric prefixes, Section 1.4 Significant figures, Table 1.5 NUCLEIC ACIDS Codons in the 5′ to 3′ sequence of mRNA, Table 14.1 Short tandem repeats (STRs) and the probability of their occurrence, Table 14.2 CARBOHYDRATES ORGANIC COMPOUNDS Monosaccharides, Table 12.1 Relative sweetness, Table 12.2 Common molecular shapes, Table 4.2 Formulas and names of alkyl groups, Table 4.6 Physical properties of selected alcohols, ethers, thiols, sulfides, and hydrocarbons, Table 11.1 Physical properties of selected aldehydes and ketones, Table 11.2 Physical properties of selected amines, Table 10.3 Physical properties of selected phenols, Table 10.2 Physical properties of some small carboxylic acids, Table 10.1 Structure, name, and properties of selected hydrocarbons, Table 4.4 The first ten numbering prefixes for IUPAC naming, Table 4.5 ENERGY Heat of fusion and heat of vaporization, Table 5.2 Specific heat, Table 5.1 GASES, LIQUIDS, AND SOLIDS Density of common substances, Table 5.5 Solutions, colloids, and suspensions, Table 7.3 The solubility of ionic compounds in water, Table 7.1 The vapor pressure of water at various temperatures, Table 5.6 HEALTH Blood pressure guidelines, Table 5.4 Concentration ranges for some blood serum solutes, Table 7.2 Dietary reference intakes (DRIs) for some essential elements, Table 2.3 RADIOACTIVITY Common forms of radioactivity, Table 2.4 Half lives and decay type for selected radioisotopes, Table 2.5 Some uses of radioisotopes in medicine, Table 2.6 CONVERSION FACTORS Mass kilogram pound milligram grain ounce = 1000 grams = 2.205 pounds = 453.59 grams = 16 ounces = 1000 micrograms = 65 milligrams = 28.3 grams Length meter kilometer mile inch = 1000 millimeters = 3.281 feet = 39.37 inches = 0.621 mile = 1.609 kilometers = 5280 feet = 2.54 centimeters quart gallon teaspoon tablespoon = 1000 milliliters = 1.057 quarts = 0.946 liter = 3.785 liters = centimeter3 = cubic centimeter = 15 drops = milliliters = 15 milliliters = 0.5 ounce Energy calorie joule = 4.184 joule = 0.2390 calorie Temperature K 0K = °C + 273.15 = −273.15 °C = −459.67°F °C = °F-32 0°C = 273.15K = 32°F = (1.8 × °C) + 32 °F Volume liter milliliter 1.8 Pressure atmosphere = 14.7 pounds per square inch = 760 torr = 760 millimeters Hg SI AND METRIC PREFIXES Prefix Symbol giga mega kilo hecto deka G M k h da deci centi milli micro nano d c m μ n Multiplier 1,000,000,000 1,000,000 1,000 100 10 0.1 0.01 0.001 0.000001 0.000000001 = 109 = 106 = 103 = 102 = 101 = 100 = 10−1 = 10−2 = 10−3 = 10−6 = 10−9 ... BIOLOGICAL CHEMISTRY An Integrated Approach SECOND EDITION GENERAL, ORGANIC, AND BIOLOGICAL CHEMISTRY An Integrated Approach SECOND Kenneth W Raymond Eastern Washington University John Wiley & Sons,... always know exactly where you stand If your instructor uses WileyPLUS, you will receive a URL for your class If not, your instructor can get more information about WileyPLUS by visiting www.wileyplus.com... FORMA CLARA VISITANOS PARA DESARGALOS GRATIS General, Organic, and Biological Chemistry: An Integrated Approach, Second Edition Kenneth W Raymond John Wiley & Sons, Inc Every one of your students