General organic and biological chemistry 5e timberlack test bank chapter 12

General, Organic & Biological Chemistry, 5e (Timberlake) Chapter 12 Introduction to Organic Chemistry: Hydrocarbons 12.1 Multiple-Choice Questions 1) In the three-dimensional structure of methane, CH4, the hydrogen atoms attached to a carbon atom are aligned A) in a straight line B) at the corners of a square C) at the corners of a tetrahedron D) at the corners of a rectangle E) at the corners of a cube Answer: C Objective: 12.1 Global Outcomes: GO2 2) In a molecule with a symmetrical arrangement of polar bonds, the overall molecule is A) highly polar B) somewhat polar C) nonpolar D) reverse polar E) strongly reverse polar Answer: C Objective: 12.1 Global Outcomes: GO2 3) Generally, a solution of an organic compound in water will be electrically A) highly conductive B) highly ionized C) nonconductive D) insulated E) charged Answer: C Objective: 12.1 Global Outcomes: GO2 4) VSEPR theory predicts that simple carbon compounds will form bonds that are A) as far apart as possible B) as close together as possible C) arranged in a straight line D) pointed to the corners of a cube E) pointed to the corners of a triangle Answer: A Objective: 12.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 5) A molecule containing a carbon atom bonded to four chlorine atoms has the shape of a A) triangle B) rhombus C) square D) cube E) tetrahedron Answer: E Objective: 12.1 Global Outcomes: GO2 6) The bond angles of tetravalent carbon are all approximately A) 90° B) 109° C) 60° D) 100° E) 45° Answer: B Objective: 12.1 Global Outcomes: GO2 7) As carbon bonds with atoms of increasingly higher electronegativities, the polarity of the bond A) decreases B) increases C) stays the same D) reverses E) becomes inverted Answer: B Objective: 12.1 Global Outcomes: GO2 8) Carbon tetrachloride has a polar C-Cl bond What is the overall polarity of the carbon tetrachloride molecule? A) weakly polar B) strongly polar C) reversed polarity D) nonpolar E) inverse polarity Answer: D Objective: 12.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 9) Which of the following is NOT typical of most organic compounds? A) high melting point B) poor solubility in water C) low boiling point D) covalent bonding E) high flammability Answer: A Objective: 12.1 Global Outcomes: GO2 10) Which one of the following is NOT an organic substance? A) an antibiotic B) nylon C) coal D) silk E) salt, sodium chloride Answer: E Objective: 12.1 Global Outcomes: GO2 11) A hydrocarbon contains only the elements A) hydrogen and oxygen B) carbon and oxygen C) carbon and hydrogen D) carbon, hydrogen, and oxygen E) carbon, hydrogen, and nitrogen Answer: C Objective: 12.1 Global Outcomes: GO2 12) Organic chemistry is the study of the chemistry of compounds of A) oxygen B) hydrogen C) living things D) polymers E) carbon Answer: E Objective: 12.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 13) How does a molecule of a vitamin synthesized in the laboratory behave when compared to the behavior of the same vitamin isolated from a natural source (e.g., vitamin C synthesized, compared to vitamin C from rose hips)? A) identical in every way B) usually identical C) Some effects are the same D) Few effects are the same E) The natural vitamin is better Answer: A Objective: 12.1 Global Outcomes: GO2 14) How many valence electrons does carbon have? A) one B) two C) three D) four E) five Answer: D Objective: 12.1 Global Outcomes: GO2 15) Carbon atoms always have how many covalent bonds? A) one B) two C) three D) four E) five Answer: D Objective: 12.1 Global Outcomes: GO2 16) An organic compound composed of carbon and hydrogen connected only by single bonds is an A) alkane B) alkene C) alkyne D) aromatic compound E) alcohol Answer: A Objective: 12.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 17) In a condensed structural formula, each carbon atom is A) shown with all individual atoms and bonds drawn B) shown with only the other carbon atoms C) grouped with its bonded hydrogen atoms D) not explicitly shown E) written in lowercase letters Answer: C Objective: 12.2 Global Outcomes: GO2 18) A formula that shows the arrangement of all bonds in a molecule is called a(n) A) molecular formula B) complete structural formula C) condensed structural formula D) condensed molecular formula E) isomeric formula Answer: B Objective: 12.2 Global Outcomes: GO2 19) Which of these formulas is the expanded structural formula for an alkane with three carbon atoms? A) C3H6 B) C3H8 C) CH3-CH2-CH3 D) C - C - C E) H H H | | | H-C-C- C-H | | | H H H Answer: E Objective: 12.2 Global Outcomes: GO2 20) What is the condensed structural formula for an alkane with four carbon atoms? A) CH3-CH=CH-CH3 B) CH3-CH2-CH2-CH3 C) C4H10 D) C - C - C - C E) H H H H | | | | H-C- C- C- C-H | | | | H H H H Answer: B Objective: 12.2 Global Outcomes: GO2 21) What is the name of the continuous chain alkane with six carbon atoms? A) butane B) pentane C) hexane D) heptane E) octane Answer: C Copyright © 2016 Pearson Education, Inc Objective: 12.2 Global Outcomes: GO2 22) What is the name of this compound? CH3- CH2- CH2- CH2- CH2- CH2- CH3 A) hexane B) heptane C) octane D) butane E) pentane Answer: B Objective: 12.2 Global Outcomes: GO2 23) What is the name of this compound? CH3- CH2- CH2- CH2- CH3 A) pentane B) hexane C) heptane D) octane E) methylbutane Answer: A Objective: 12.2 Global Outcomes: GO2 24) What is the name of CH3- CH2- CH2- CH3? A) ethane B) propane C) butane D) pentane E) hexane Answer: C Objective: 12.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 25) What is the name of this compound? A) ethane B) propane C) butane D) pentane E) hexane Answer: E Objective: 12.2 Global Outcomes: GO2 26) What is the name for a four-carbon continuous-chain alkane? A) methane B) ethane C) propane D) butane E) pentane Answer: D Objective: 12.2 Global Outcomes: GO2 27) What is the name for a five-carbon continuous-chain alkane? A) methane B) ethane C) propane D) butane E) pentane Answer: E Objective: 12.2 Global Outcomes: GO2 28) What is the mame for a six-carbon continuous-chain alkane? A) hexane B) heptane C) octane D) nonane E) decane Answer: A Objective: 12.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 29) What is the name for a seven-carbon continuous-chain alkane? A) hexane B) heptane C) octane D) nonane E) decane Answer: B Objective: 12.2 Global Outcomes: GO2 30) What is the name for an eight-carbon continuous-chain alkane? A) hexane B) heptane C) octane D) nonane E) decane Answer: C Objective: 12.2 Global Outcomes: GO2 31) What is the name for a nine-carbon continuous-chain alkane? A) hexane B) heptane C) octane D) nonane E) decane Answer: D Objective: 12.2 Global Outcomes: GO2 32) What is the name for a ten-carbon continuous-chain alkane? A) hexane B) heptane C) octane D) nonane E) decane Answer: E Objective: 12.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 33) What is the name of this compound? A) cyclopentane B) cyclohexane C) cycloheptane D) cyclooctane E) hexane Answer: B Objective: 12.2 Global Outcomes: GO2 34) What is the name of this compound? A) cyclopentane B) cyclohexane C) cycloheptane D) cyclooctane E) pentane Answer: A Objective: 12.2 Global Outcomes: GO2 35) The IUPAC name for CH3 -Cl is A) methyl chloride B) chloromethane C) methanechlorine D) chloroethane E) methane chloride Answer: B Objective: 12.3 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 36) Which of the following pairs of compounds are structural isomers? A) Cl Cl | | CH3 C HCH2 CH3 and CH3CH2 C HCH3 B) ClCH2CH2CH2CH3 and CH3CH2CH2CH2Cl C) CH3CHCH3 and CH3CHCH2Cl | | CH2Cl CH3 D) Cl | CH3CHCH3 and CH3 C CH3 | | CH2Cl CH3 E) Answer: D Objective: 12.3 Global Outcomes: GO2 37) What is the IUPAC name for the following? CH3 ∣ CH3-CH2-CH2-CH- CH2-CH3 A) 4-methylhexane B) 3-methylhexane C) heptane D) methylhexane E) 2-methylhexane Answer: B Objective: 12.3 Global Outcomes: GO2 10 Copyright © 2016 Pearson Education, Inc 77) What is the condensed structural formula of the compound propene? A) CH3-CH2-CH3 B) H3C = CH2-CH3 C) H2C = C = CH2 D) CH3-CH = CH2 E) HC ≡ C-CH3 Answer: D Objective: 12.5 Global Outcomes: GO2 78) What is the condensed structural formula for the compound 3-hexene? A) CH3 | CH3-CH2-C H-CH2-CH3 B) CH2 = CH-CH2 -CH2 -CH2 -CH3 C) CH3-CH2-CH = CH-CH2-CH3 D) CH3-CH2-CH2-CH = CH-CH3 E) CH3-CH = CH-CH2-CH2-CH3 Answer: C Objective: 12.5 Global Outcomes: GO2 79) The compound 1-butyne contains A) all single bonds B) a double bond C) a triple bond D) a ring structure E) a bromine atom Answer: C Objective: 12.5 Global Outcomes: GO2 80) What is the IUPAC name for the following compound? A) 1-pentene B) 2-pentene C) 3-pentene D) 1-methylbutene E) 2-pentyne Answer: B Objective: 12.5 Global Outcomes: GO2 22 Copyright © 2016 Pearson Education, Inc 81) What is the IUPAC name for the following compound? A) 3-methyl-4-pentene B) 4-methyl-3-pentene C) 2-methyl-2-pentene D) 2-methyl-3-pentene E) hexene Answer: C Objective: 12.5 Global Outcomes: GO2 82) What is the IUPAC name for the following compound? A) 6-chloro-2-pentyne B) 6-chloro-1-pentyne C) 1-chloro-5-hexyne D) 6-chloro-1-heptyne E) 6-chloro-1-hexyne Answer: E Objective: 12.5 Global Outcomes: GO2 83) Which of the following compounds have cis-trans isomers? A) CH2 = CH - CH3 B) CCl2 = CBr2 C) CH3 - CH = CH - CH3 D) CCl2 = CHBr E) All of the above have cis-trans isomers Answer: C Objective: 12.6 Global Outcomes: GO2 84) Some alkenes have cis-trans isomers because A) the carbon atoms in the double bond cannot rotate B) each of the carbon atoms in the double bond has four different groups attached to it C) one of the carbon atoms in the double bond has two identical groups attached to it D) the carbon atoms in the double bond are free to rotate E) all of the carbon atoms in the compound are rigid and cannot rotate Answer: A Objective: 12.6 Global Outcomes: GO2 23 Copyright © 2016 Pearson Education, Inc 85) Which of the following pairs of compounds are cis-trans isomers? A) B) C) HC ≡ C - CH3 and CH3 - C ≡ CH D) E) Answer: E Objective: 12.6 Global Outcomes: GO2 86) What is the name of the compound shown below? A) 2-pentene B) trans-2-pentene C) trans-3-pentene D) cis-2-pentene E) cis-3-pentene Answer: B Objective: 12.6 Global Outcomes: GO2 87) The reaction of hydrogen (H2) and propene using a platinum catalyst is called A) combustion B) substitution C) addition D) neutralization E) condensation Answer: C Objective: 12.7 Global Outcomes: GO2 24 Copyright © 2016 Pearson Education, Inc 88) The hydrogenation of an alkene gives a(n) A) alkane B) alkene C) alkyne D) benzene E) isomer Answer: A Objective: 12.7 Global Outcomes: GO2 89) What is the condensed structural formula for the product of the hydrogenation of 2butene using a platinum catalyst? A) CH3-CH= CH-CH3 B) Cl | CH3-CH2- CH-CH3 C) CH3-CH2-CH2-CH3 D) CH3 | CH3- CH-CH3 E) OH | CH3- CH-CH3 Answer: C Objective: 12.7 Global Outcomes: GO2 90) According to Markovnikov's rule, the hydrogen in HOH (water) adds to the carbon in the double bond A) attached to the end carbon B) that has the smaller number of hydrogen atoms attached C) that has the greater number of hydrogen atoms attached D) that has the smaller number of carbon atoms attached E) that has the greater number of carbon atoms attached Answer: C Objective: 12.7 Global Outcomes: GO2 91) The reaction of an alkene and water in the presence of an acid catalyst to produce an alcohol is called A) hydrolysis B) alkoholysis C) halogenation D) hydration E) hydrohydration Answer: D Objective: 12.7 Global Outcomes: GO2 92) What is the major product of the reaction shown below? CH3- CH2- CH = CH2 + HOH A) OH | OH | 25 Copyright © 2016 Pearson Education, Inc CH3 - CH2 - CH - CH2 B) OH | CH3 - CH2 - CH - CH3 C) CH3 - CH2 - CH2 - CH2 OH D) OH OH | | CH3 - CH - CH - CH3 E) OH | CH3 - CH2 - C - CH2 Answer: B Objective: 12.7 Global Outcomes: GO2 93) Long-chain molecules that consist of many repeating units are called A) polymers B) monomers C) organic compounds D) alkenes E) alkanes Answer: A Objective: 12.7 Global Outcomes: GO2 94) Small molecules that make up the repeat unit in polymers are called A) monomers B) alkenes C) alkynes D) minipolymers E) synthetic polymers Answer: A Objective: 12.7 Global Outcomes: GO2 26 Copyright © 2016 Pearson Education, Inc 95) What is the starting monomer for the polymer Teflon®? F F | | -C- C | | F F F | - C | F F | -C| F A) F | F-C-F | F B) F | H-C-H | F C) F F | | F-C- C-F | | F F D) C F E) F F | | F-C C-F Answer: E Objective: 12.7 Global Outcomes: GO2 27 Copyright © 2016 Pearson Education, Inc 96) Which of the following would result from the polymerization of ethene? A) CH3 CH3 | | - C - CH2 - C - CH2 | | CH3 CH3 B) CH3 CH3 CH3 CH3 | | | | -C - C - C - C | | | | H H H H C) H H H H | | | | -C=C-C=CD) = C = C = C = C = E) - CH2 - CH2 - CH2 - CH2 Answer: E Objective: 12.7 Global Outcomes: GO2 97) The structural formula of benzene is often represented as a A) ring of five carbon atoms B) ring of six carbon atoms with six double bonds C) ring of six carbon atoms with a circle in the center D) cycloalkane E) cycloalkyne Answer: C Objective: 12.8 Global Outcomes: GO2 98) A compound that contains the ring structure of benzene is called a(n) A) alkane B) cycloalkane C) alkyl group D) aromatic compound E) hydrocarbon Answer: D Objective: 12.8 Global Outcomes: GO2 28 Copyright © 2016 Pearson Education, Inc 99) The compound below is named A) cyclohexane B) cyclohexene C) cyclohexyne D) benzene E) cyclobenzene Answer: D Objective: 12.8 Global Outcomes: GO2 100) What is the molecular formula of benzene? A) C6H4 B) C6H6 C) C6H8 D) C6H10 E) C6H12 Answer: B Objective: 12.8 Global Outcomes: GO2 101) All of the carbon-carbon bonds in benzene are A) composed of only two types, single and double B) identical C) double bonds D) single bonds E) circular bonds Answer: B Objective: 12.8 Global Outcomes: GO2 29 Copyright © 2016 Pearson Education, Inc 102) What is the name of the compound below? A) 1-chlorotoluene B) 2-chlorotoluene C) 3-chlorotoluene D) 4-chlorotoluene E) 5-chlorotoluene Answer: B Objective: 12.8 Global Outcomes: GO2 12.2 True/False Questions 1) Organic chemistry is the study of the chemistry of carbon compounds Answer: TRUE Objective: 12.1 Global Outcomes: GO2 2) There are millions of organic compounds Answer: TRUE Objective: 12.1 Global Outcomes: GO2 3) Carbon has six valence electrons Answer: FALSE Objective: 12.1 Global Outcomes: GO2 4) Methane has a tetrahedral structure Answer: TRUE Objective: 12.1 Global Outcomes: GO2 5) The bond angles in a tetrahedral molecule are 90° Answer: FALSE Objective: 12.1 Global Outcomes: GO2 6) Organic compounds are always highly water soluble Answer: FALSE Objective: 12.1 Global Outcomes: GO2 30 Copyright © 2016 Pearson Education, Inc 7) Most organic compounds are flammable Answer: TRUE Objective: 12.1 Global Outcomes: GO2 8) Organic compounds can only be made by living things because a "vital force" is needed for their creation Answer: FALSE Objective: 2.1 Global Outcomes: GO2 9) Most prescription drugs are organic molecules Answer: TRUE Objective: 2.1 Global Outcomes: GO2 10) Pentane contains six carbon atoms Answer: FALSE Objective: 12.2 Global Outcomes: GO2 11) The name of this alkane is pentane Answer: FALSE Objective: 12.2 Global Outcomes: GO2 12) Octane is a seven-carbon continuous chain alkane Answer: FALSE Objective: 12.2 Global Outcomes: GO2 13) Octane is a seven-carbon linear alkane Answer: FALSE Objective: 12.2 Global Outcomes: GO2 14) In a condensed structural formula, the carbon and attached hydrogens are written as a group Answer: TRUE Objective: 12.2 Global Outcomes: GO2 15) The first four linear alkyl substituent groups are named methyl, ethyl, propyl, and butyl Answer: TRUE Objective: 12.3 Global Outcomes: GO2 31 Copyright © 2016 Pearson Education, Inc 16) When naming an alkane, the main chain is the longest continuous carbon chain regardless of bends Answer: TRUE Objective: 12.3 Global Outcomes: GO2 17) The name of this alkane is 3,4-dimethylhexane Answer: TRUE Objective: 12.2 Global Outcomes: GO2 18) The products of complete combustion are carbon dioxide and water Answer: TRUE Objective: 12.4 Global Outcomes: GO2 19) Organic liquids are often less dense than water Answer: TRUE Objective: 12.4 Global Outcomes: GO2 20) Mineral oil is a liquid hydrocarbon used as a laxative and lubricant in medical practice Answer: TRUE Objective: 12.4 Global Outcomes: GO2 21) Solid alkanes are found on the surface of many fruits and vegetables Answer: TRUE Objective: 12.4 Global Outcomes: GO2 22) Propylene is used to induce ripening in fruits Answer: FALSE Objective: 12.5 Global Outcomes: GO2 23) Alkynes contain double bonds Answer: FALSE Objective: 12.5 Global Outcomes: GO2 24) An alkyne containing three carbons is named propyne Answer: TRUE Objective: 12.5 Global Outcomes: GO2 25) Light-induced cis-trans isomerization is an important step in vision Answer: TRUE Objective: 12.6 Global Outcomes: GO2 26) In a cis alkene, the groups are on the same side of the double bond 32 Copyright © 2016 Pearson Education, Inc Answer: TRUE Objective: 12.6 Global Outcomes: GO2 27) In a trans alkene, the groups are on the same side of the double bond Answer: FALSE Objective: 12.6 Global Outcomes: GO2 28) All alkenes show cis-trans isomerism Answer: FALSE Objective: 12.6 Global Outcomes: GO2 29) Alkynes can show cis-trans isomerism Answer: FALSE Objective: 12.6 Global Outcomes: GO2 30) Hydrogenation is used to convert alkenes to alkanes Answer: TRUE Objective: 12.7 Global Outcomes: GO2 31) Hydration is used to convert alkenes to alkanes Answer: FALSE Objective: 12.7 Global Outcomes: GO2 32) Hydrogenation of unsaturated vegetable oils raises the melting point and makes them more solid Answer: TRUE Objective: 12.7 Global Outcomes: GO2 33) Water can be added to alkenes to produce acids Answer: FALSE Objective: 12.7 Global Outcomes: GO2 34) Polymers are large molecules consisting of repeating units Answer: TRUE Objective: 12.7 Global Outcomes: GO2 33 Copyright © 2016 Pearson Education, Inc 35) Nylon, polyester, and most other plastics are carbon compounds Answer: TRUE Objective: 12.7 Global Outcomes: GO2 36) One essential building block of aspirin, ibuprofen, and acetaminophen is the benzene ring Answer: TRUE Objective: 12.8 Global Outcomes: GO2 37) All polycyclic aromatic compounds cause cancer Answer: FALSE Objective: 12.8 Global Outcomes: GO2 38) The chemical formula for benzene is C6H12 Answer: FALSE Objective: 12.8 Global Outcomes: GO2 12.3 Matching Questions Identify the following as more characteristic of an organic compound or an inorganic compound A) organic B) inorganic 1) high melting point Objective: 12.1 Global Outcomes: GO2 2) flammable Objective: 12.1 Global Outcomes: GO2 3) covalent bonds Objective: 12.1 Global Outcomes: GO2 4) insoluble in water Objective: 12.1 Global Outcomes: GO2 5) ionic bonds Objective: 12.1 Global Outcomes: GO2 Answers: 1) B 2) A 3) A 4) A 5) B 34 Copyright © 2016 Pearson Education, Inc Match the following organic structures with the appropriate classification A) aromatic compound B) alkene aromatic C) alkane D) cycloalkane E) cycloalkene 6) Objective: 12.5 Global Outcomes: GO2 7) CH3-CH2-CH2-CH3 Objective: 12.5 Global Outcomes: GO2 8) Objective: 12.5 Global Outcomes: GO2 9) Objective: 12.5 Global Outcomes: GO2 Answers: 6) A 7) C 8) D 9) E 35 Copyright © 2016 Pearson Education, Inc Choose the type of compound from Column that best matches each item in Column A) cycloalkene B) cycloalkane C) alkane D) haloalkane E) alkene 10) CH3- CH = CH - CH3 Objective: 12.5 Global Outcomes: GO2 11) CH4 Objective: 12.5 Global Outcomes: GO2 12) Objective: 12.5 Global Outcomes: GO2 13) CH3-CH2-Cl Objective: 12.5 Global Outcomes: GO2 14) Objective: 12.5 Global Outcomes: GO2 15) CH3 | CH2 | CH3 Objective: 12.5 Global Outcomes: GO2 Answers: 10) E 11) C 12) B 13) D 14) A 15) C 36 Copyright © 2016 Pearson Education, Inc ... hydrogen and oxygen B) carbon and oxygen C) carbon and hydrogen D) carbon, hydrogen, and oxygen E) carbon, hydrogen, and nitrogen Answer: C Objective: 12. 1 Global Outcomes: GO2 12) Organic chemistry. .. C6H12 Answer: FALSE Objective: 12. 8 Global Outcomes: GO2 12. 3 Matching Questions Identify the following as more characteristic of an organic compound or an inorganic compound A) organic B) inorganic... 5-chlorotoluene Answer: B Objective: 12. 8 Global Outcomes: GO2 12. 2 True/False Questions 1) Organic chemistry is the study of the chemistry of carbon compounds Answer: TRUE Objective: 12. 1 Global Outcomes: