Organic Chemistry Test Bank PDF

Chapter 1  Part III Test Bank Chapter 1 Bonding and Isomerism Valence, Bonding, and Lewis Structures 1.1. What is the most electropositive element? *a. Li b. Be c. B d. C e. N 1....

Chapter 1  Part III Test Bank Chapter 1 Bonding and Isomerism Valence, Bonding, and Lewis Structures 1.1. What is the most electropositive element? *a. Li b. Be c. B d. C e. N 1.2. Which of the following elements has 5 electrons in the valence (outer) shell? a. C b. B c. S d. F *e. P 1.3. Which of the following would you expect to have ionic bonds? *a. MgF2 b. CO c. ICl d. Br2 e. NF3 1.4. Which of the following would you expect to have polar covalent bonds? a. MgF2 b. N2 c. F2 *d. NF3 e. NaF 1.5. Which molecule has nonpolar covalent bonds? a. NO *b. N2 c. BCl3 d. HF e. CCl4 1.6. The number of electrons in the valence shell of aluminum is: a. 1 b. 2 *c. 3 d. 4 e. 5 1.7. Which of the following elements is the most electronegative? *a. O b. S c. Se d. Te e. Po 1.8. If the Cl–Cl bond length is 1.98Å and the C–C bond length is 1.54Å, what would you expect the bond length of Cl–C to be? a. 0.74Å b. 1.54Å *c. 1.76Å d. 1.98Å e. 3.52Å 1.9. Given the following electronegativity values, predict the most polar covalent bond below: F 4.0 Cl 3.0 O 3.5 C 2.5 H 2.1 *a. C–F b. C–Cl c. C–O d. C–H e. C–C 1.10. The most electronegative elements in the periodic table are generally found a. toward the left in a horizontal row and toward the top in a column. *b. toward the right in a horizontal row and toward the top in a column. c. toward the left in a horizontal row and toward the bottom in a column. d. toward the right in a horizontal row and toward the bottom in a column. e. distributed randomly throughout the table. 36 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 37 1.11. In which of the following electron-dot formulas is the Formal Charge incorrectly assigned? _ + _ + a. H C N *b. H C N. c. H C N _ + d. H C N e. H C N Structural Isomers 1.12. Which of the following molecules are structural isomers?. OH O. CH3CH2CH2OH CH3CH2OCH3 CH3CHCH3 CH3CCH3. 1 2 3. 4 a. 1, 2, and 4 *b. 1, 2, and 3 c. 1, 3, and 4 d. 2, 3, and 4 e. 3 and 4 1.13. Which of the following abbreviated structural formulas is NOT an isomer of the others? a. b. c. *d. e. 1.14. The number of possible acyclic hydrocarbons with the molecular formula C4 H6 is a. 2 b. 3 *c. 4 d. 5 e. 6 1.15. Which of the following structural formulas represents a structural isomer of CH3CH2CH2CH2CH3?. a. CH3CH2CH2 b. CH3CH2CHCH3 c. (CH3)2CHCH3. CH2CH3 CH2CH3 *d. CH3CH2CH(CH3)2 e. CH2CH2CH3 CH3. Copyright © Houghton Mifflin Company. All rights reserved. 38 PART III 1.16. Which of the following molecules are structural isomers?. CH2CH2CH2CH3 CH2CH2CH2CH3 CH3CH2 CHCH3 CH2CH3 CH3 CH2CH3. 1 2 3 CH2CH2CH2CH3 (CH3)2CH CH(CH3)2 CH2CH2OH 4 5. a. 1, 2 and 3 b. 1, 3 and 4 c. 2, 3 and 5 *d. 1, 3 and 5 e. 2 and 3 1.17. Which of the following abbreviated structural formulas represents a structural isomer of CH3CH2CH2CH2CH3? a. *b. c. d. e. Structural Formulas 1.18. The structural formula for (CH3 )2C(CH2CH3 )2 is. a. CH3CH3CCH2CH3CH2CH3 b. CH3CH2CH3 CH3CH2CH3. H2 H3C CH2CH3 C C c. H3C CH3 *d. C H3C CH2CH3 H3C CH3 C H2 e. C7H16. 1.19. The structural formula has the molecular formula a. C6 H10 *b. C8 H14 c. C8 H16 d. C8 H18 e. C8 H20 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 39 1.20. Which of the following structural formulas does not have the molecular formula C6 H14?. a. b. (CH3)3CCH2CH3 c. *d. (CH3)2CHCH2CH3 e. 1.21. Which of the following structural formulas has the molecular formula C6 H12? 1 2 3 4 5 a. 2 and 3 b. 1 and 4 *c. 1, 4, and 5 d. 1 and 2 e. 4 and 5 1.22. The structural formula for (CH3CH2 )2CHCH2CH(CH3)2 is CH3 a. C9H20 *b. CH3CH2CHCH2CHCH3 CH2CH3 CH3 CH3CH2 CH3 c. CH3CH2CH2CHCHCH3 d. CHCH CH3CH2 CH3 CH2CH3 CH3 e. CH3CH2CH2CH2CH2CH2CH CH3 1.23. The structural formula has the molecular formula a. C7H16 b. C6H14 *c. C7H14 d. C6H12 e. C7H12 Copyright © Houghton Mifflin Company. All rights reserved. 40 PART III 1.24. The structural formula CH3 C H3C CH2 has the molecular formula *a. C10H16 b. C9H18 c. C10H22 d. C6H14 e. C10H18 Formal Charge, Resonance, and Curved-Arrow Formalism 1.25. For carbon C O , C has a formal charge of: monoxide, a. +1 *b. –1 c. 0 d. –2 e. +2 1.26. For carbon C O , O has a formal charge of: monoxide, *a. +1 b. –1 c. 0 d. –2 e. +2 1.27. What is the formal charge of N in HNO3 , as seen below? O H O N O *a. +1 b. +2 c. 0 d. –1 e. –2 1.28. The formal charges in the perchlorate ion are. O. O Cl O O. *a. –1 on each O and +3 on the Cl. b. 0 on each O and –1 on the Cl. c. –1 on each O and +4 on the Cl. d. –1/4 on each O and 0 on the Cl. e. +1 on each O and –1 on the Cl. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 41 1.29. Which of the following structures is a resonance structure of. _ O. C. H3C + CH3.. H2C H2C CH2 O a. CHOH b. *c. H2C H2C O C H3C CH3. O O d. C e. H3C HC CH2 H CH2CH3. 1.30. The formal charges in the complex. H H H B N H H H. are *a. 0 on each H, +1 on N, and –1 on B. b. +1 on each H, +1 on N, and –1 on B. c. 0 on each H, –1 on N, and +1 on B. d. 0 on each H, 0 on N, and 0 on B. e. –1 on each H, +3 on N, and +3 on B. 1.31. The curved arrows in the resonance structure for the acetate ion shown below O H3C C O _ indicate the following alternative resonance structure for the acetate ion: _ _ O O O a. H3C C b. H3C C *c. H3C C O _ O O _ O O d. H3C C e. H3C C O O _ Copyright © Houghton Mifflin Company. All rights reserved. 42 PART III Electronic Structure and Molecular Geometry 1.32. What is the percent s character in an sp3 hybridized orbital? *a. 25% b. 33% c. 50% d. 67% e. 75% 1.33. The maximum number of electrons that a molecular orbital can contain is: a. 1 *b. 2 c. 3 d. 4 e. 5 1.34. The approximate H–C–H bond angle in methane is: a. 60° b. 90° *c. 109.5° d. 120° e. 180° 1.35. The Lewis structure of methane is H H C H H. The approximate H–C–H bond angle in methane is a. 60o b. 90o *c. 109.5o d. 120o e. 180o Classification of Organic Compounds 1.36. Which of the following molecules is carbocyclic? a. CH3CH2CH3 *b. c. CH3CHCH3. CH3 d. e. CH3OCH2CH3 1.37. Which of the following molecules contain the same functional group? CH3 OH CH3OCH3 CH3CH2 OH CH3CH(OH)CH3 1 2 3 4 a. 1, 2 and 3 *b. 1, 3 and 4 c. 1 and 2 d. 2 and 4 e. 3 and 4 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 43 1.38. Which of the following molecules is acyclic?. OH. a. *b. c. O d. e. 1.39. Which of the following molecules is heterocyclic?. OH. *a. b. c. N d. e. 1.40. Which of the following molecules contain the same functional group?. OCH3 CH3CHCH3 CH3CH2CH2OH CH3CH2CH2SH OH 1 2 3 4 a. 1, 2 and 3 b. 1, 2 and 4 c. 2 and 4 *d. 1 and 2 e. 1 and 3 Copyright © Houghton Mifflin Company. All rights reserved. Chapter 2  Chapter 2 Alkanes and Cycloalkanes; Conformational and Geometric Isomerism Alkane Nomenclature and Structural Formulas 2.1. What is the molecular formula of an alkane that has fourteen carbon atoms? a. C14H28 *b. C14H30 c. C14H32 d. C14H34 e. C14H26 2.2. What is the molecular formula of a cycloalkane that has five carbon atoms? *a. C5H10 b. C5H12 c. C5H14 d. C5H8 e. C5H5 2.3. What is the name of the alkane that has two carbon atoms? a. methane *b. ethane c. propane d. butane e. isobutane 2.4. The correct IUPAC name for the following molecule is: CH3 CH3CH2CHCHCH2CHCH3 CH3 CH2CH3 a. 6-ethyl-3,4,-dimethylheptane b. 2-ethyl-4,5-dimethylheptane *c. 3,4,6-trimethyloctane d. 3,5,6-trimethyloctane e. none of these 2.5. What is the common name for the following molecule?.. CH3CHCH2Br. CH3. *a. isobutyl bromide b. tert-butyl bromide c. butyl bromide d. sec-butyl bromide e. bromo-sec-butane 2.6. The name of the alkyl group that contains two carbons is: a. methyl *b. ethyl c. propyl d. isopropyl e. none of these 44 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 45 2.7. Which of the following structures is 2-methylpentane?. a. CH3CH2CH2CH2CH3 *b. CH3CHCH2CH2CH3 c. CH3 CH3 CH3CCH3. CH3 d. e. CH3CH2CHCH3 CH3. 2.8. The name of the alkyl group below is: CH3CH CH3 a. ethyl b. propyl *c. isopropyl d. butyl e. isobutyl 2.9. What is the IUPAC name for the following compound?. Br. CH3CH2CHCHCH3. CH3. a. isohexyl bromide b. 3-bromo-4-methylpentane c. 1-bromopropylpropane *d. 3-bromo-2-methylpentane e. 2-methyl-3-bromopentane 2.10. The IUPAC name for the following molecule is:.. CH3CH2CHClC(CH3)3.. a. 3-chloroheptane b. 2-chloro-1,1,1-trimethylbutane c. t-butylpropyl chloride d. 3-chloro-1-dimethylpentane *e. 3-chloro-2,2-dimethylpentane 2.11. Which of the following structures is tert-butyl iodide?. a. CH3CH2CH2CH2I b. CH3CHCH2CH2I c. CH3CHCH2CH3. CH3 I I *d. CH3CCH3 e. CH3CH I CH3 CH3. Copyright © Houghton Mifflin Company. All rights reserved. 46 PART III 2.12. What is a correct name for the following molecule?. Cl. Cl.. a. 2,2-dichlorocyclopropane b. 1,1-dichlorocyclopentane c. 1,1-dichloropropane d. trans-1,1-dichlorocyclopropane *e. 1,1-dichlorocyclopropane 2.13. Trans-1-bromo-3-methylcyclobutane is represented by which structure below? Br Br Br a. b. *c. CH3 H3C H3C CH3 Br d. e. Br H3C 2.14. What is the correct name for the following cycloalkane?. Br CH2CH3 H H. a. bromoethylcyclohexane b. trans-1-ethyl-3-bromocyclohexane c. cis-3-bromo-1-ethylhexane d. 1-bromo-3-ethylcyclohexane *e. cis-1-bromo-3-ethylcyclohexane 2.15. The correct IUPAC name for (CH3 )2CHCH(CH3 )(CH2 )3CH(CH3 )2 is a. diisopropylpentane. b. 1,1,2,6,6-pentamethylhexane. c. 2,5-diisopropylpentane. *d. 2,3,7-trimethyloctane. e. 1,4-diisopropylpentane. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 47 2.16. The correct IUPAC name for. CH3 CH3 H3C H. is a. 1,3,3-trimethylcyclobutane. b. cis-1,3,3-trimethylcyclobutane. c. trans-1,3,3-trimethylcyclobutane. *d. 1,1,3-trimethylcyclobutane. e. 2,2,4-trimethylcyclobutane. 2.17. The structural formula for 2,2,3-trimethylhexane is. a.. b.. c.. (CH3)2CCH2CH3. *d. CH3.. e.. (CH3)3CCHCH3. CH3. Alkane Properties 2.18. Which of the following would exhibit hydrogen bonding? a. CH3Cl *b. CH3OH c. CH4 d. CH2Cl2 e. CH3CH3 2.19. Which of the following alkanes would have the highest boiling point? a. pentane b. isopentane c. neopentane *d. hexane e. isohexane 2.20. What statement does NOT apply to the boiling points of alkanes? a. The boiling point increases as the length of the carbon chain increases. b. Straight chain alkanes have a higher boiling point than their branched isomers. c. Because they are nonpolar, alkanes have lower boiling points than other organic compounds of similar molar mass. d. The boiling points are affected by Van der Waals attractions. *e. The boiling points are influenced by hydrogen bonding. Copyright © Houghton Mifflin Company. All rights reserved. 48 PART III 2.21. Which cycloalkane has the highest boiling point? a. cyclopropane b. cyclobutane c. cyclopentane d. cyclohexane *e. cyclooctane 2.22. The boiling points of normal alkanes a. rise as the length of the carbon chain increases. b. rise as the length of the carbon chain decreases. c. are higher than the boiling points of branched alkanes with the same molecular formula. *d. a and c e. b and c Conformations of Alkanes 2.23. The most stable conformation of propane is: *a. staggered b. chair c. planar d. eclipsed e. boat 2.24 The least stable conformation of propane is: a. staggered b. chair c. planar *d. eclipsed e. boat 2.25. The preferred conformation of butane is given by which of the following Newman projection formulas?. H CH3 H CH3 H3C H H H *a. b. c. CH3. H CH3 H CH3 H H CH3 H H CH2CH3 CH3 H H H H d. e. H H H3C CH3 H. H Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 49 2.26. The least stable conformation of butane is given by which of the following Newman projections? H CH3 H3C CH3 H3C H H H a. b. *c. H H CH3 H CH3 H H CH3 H H CH2CH3 H CH3 H H d. e. CH3 H H H H H H Conformations of Cycloalkanes 2.27. The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which: a. the t-butyl group is axial and the methyl group is equatorial b. both groups are axial *c. both groups are equatorial d. the methyl group is axial and the t-butyl group is equatorial e. molecule exists in a boat conformation 2.28. The bond angle of a normal, tetrahedral, sp3 hybridized carbon is 109.5°. What is the C–C–C bond angle of cyclopropane? *a. 60° b. 90° c. 109.5° d. 120° e. 180° 2.29. For the most stable conformation of trans-1,2-dimethylcyclohexane: a. both methyls will occupy the axial position *b. both methyls will occupy the equatorial position c. one methyl will occupy the axial position and the other an equatorial position d. more than one answer is correct 2.30. Which of the following pairs are examples of conformational isomerism? *a. chair and boat forms of cyclohexane b. 1-iodopropane and 2-iodopropane c. sec-butyl chloride and butyl iodide d. cis and trans-1,2-dimethylcyclohexane e. all of these Copyright © Houghton Mifflin Company. All rights reserved. 50 PART III 2.31. Consider this chair conformation:. CH3 H3C H H H Br. When the ring flips, a. the bromine becomes axial and the methyls become equatorial. b. all three substituents become equatorial. *c. the bromine becomes equatorial and the methyls become axial. d. the ring opens up. e. one methyl becomes axial, one becomes equatorial, and the bromine becomes equatorial. 2.32. Consider this chair conformation: CH3 H Cl Br H H. *a. The methyl and bromine are cis and the chlorine and bromine are cis. b. The methyl and bromine are trans and the chlorine and bromine are cis. c. The methyl and chlorine are trans and the methyl and bromine are cis. d. The methyl and chlorine are trans and the methyl and bromine are trans. e. The methyl and chlorine are trans and the bromine and chlorine are cis. 2.33. Cycloalkanes with __________ or more carbons in the ring are nonplanar. a. 2 b. 3 *c. 4 d. 5 e. 6 Isomerism 2.34. 1-Bromopropane and 2-bromopropane are *a. constitutional isomers. b. homologs. c. configurational isomers. d. conformational isomers. e. stereoisomers. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 51 2.35. The compounds represented by the structures CH3 CH3 H H and H HC 3 CH3 H are a. structural isomers. b. identical. *c. cis-trans isomers. d. conformers. e. constitutional isomers. 2.36. The compounds represented by the structures CH3 H and H CH3 are a. structural isomers. *b. identical. c. cis-trans isomers. d. conformers. e. constitutional isomers. 2.37. The compounds represented by the structures Cl H and Cl H are a. structural isomers. b. identical. c. cis-trans isomers. *d. conformers. e. constitutional isomers. 2.38. The compounds represented by the structures CH3 CH3 H and CH3 CH3 H H H are *a. structural isomers. b. identical. c. cis-trans isomers. d. conformers. e. stereoisomers. Copyright © Houghton Mifflin Company. All rights reserved. 52 PART III Reactions of Alkanes 2.39. In the chlorination of methane, the propagation steps involve forming: a. H radicals b. methyl radicals c. chlorine radicals d. a, b, and c *e. b and c 2.40. How many monobromo products can be obtained from the bromination of cyclopentane? *a. 1 b. 2 c. 3 d. 4 e. 5 2.41. How many isomeric dichloro products can be obtained from the chlorination of cyclopropane? a. 1 b. 2 *c. 3 d. 4 e. 5 2.42. The number of possible monobromination products, including cis-trans isomers, of methylcyclopentane is a. 2 b. 3 c. 4 d. 5 *e. 6 2.43. The number of possible dibromination products of 2-methylpropane is a. 2 *b. 3 c. 4 d. 5 e. 2.44. The number of possible dichlorination products of propane is a. 2 b. 3 *c. 4 d. 5 e. 6 Copyright © Houghton Mifflin Company. All rights reserved. Chapter 3  Chapter 3 Alkenes and Alkynes Alkenes and Alkynes: Nomenclature and Structure 3.1. Which of the following dienes can be classified as conjugated? a. CH3CH=C=CH2 *b. CH3CH=CHCH=CH2 c. CH2=CHCH2CH=CH2 d. CH3CH=CHCH2CH2CH=CH2 e. CH2=C=CH2 3.2. Which of the following molecular formulas could not represent an alkene? a. C5H10 b. C7H14 c. C10H20 *d. C27H56 e. C31H62 3.3. What is the correct name for the following molecule? CH2CH3 a. 1-ethylcyclohexene b. 2-ethylcyclohexene *c. 3-ethylcyclohexene d. cyclohexylethane e. 1-ethyl-3-cyclohexene 3.4. Which of the following compounds can exhibit cis/trans isomerism? a. 1-pentene *b. 2-pentene c. 2-methyl-2-pentene d. 3-methyl-1-pentene e. 1-hexene 3.5. The correct IUPAC name for the following molecule is:. H3C Cl C C Cl CH2CHCH3 CH3. *a. trans-2,3-dichloro-5-methyl-2-hexene b. trans-2,3-dichloro-5-methyl-3-hexene c. cis-2,3-dichloro-5-methyl-3-hexene d. trans-4,5-dichloro-2-methyl-4-hexene e. cis-4,5-dichloro-2-methyl-4-hexene 3.6. What is the correct structure for 2,3-dimethyl-2-pentene? CH3 CH3. a. CH3C CHCHCH3 b. CH2 CCHCH2CH3 c. CH3CHCH CCH3 CH3 CH3 CH3 CH3 CH3 CH3 *d. CH3C CCH2CH3 e. CH3CHCHCH CH2 CH3 CH3. 53 Copyright © Houghton Mifflin Company. All rights reserved. 54 PART III 3.7. The correct structure for allyl bromide is:. *a. CH2 CHCH2Br b. CH2 CHBr c. BrCH CHBr. d. BrCH CHCH3 e. CH2 CHCHBr2. 3.8. Which of the following molecules is 4-methyl-2-hexyne?. *a. CH3C CCHCH2CH3 b. CH3CH2C CCH2CH3. CH3 c. CH3CHCH2C CCH3. d. CH3C CCH2CHCH3 CH3 CH3.. e. CH3CHC CCH2CH3. CH3 3.9. The correct name of the molecule below is:.. HC CCH2CH2CHCH2CH CH2. CH3. a. 5-methyl-7-octen-1-yne *b. 4-methyl-1-octen-7-yne c. 4-methyl-1-octyn-7-ene d. 5-methyl-1-octen-7-yne e. none of these is correct 3.10. The multiple bonds in the following compounds are conjugated: 1. CH2 C CH2 4. CH3 2. CH2 C C CH2 5. CH3 C C CH CH2. CH3 3. CH2 CH CH O 6. *a. 2, 3, and 5 b. 4 and 6 c. only 1 d. 2 and 3 e. 2 and 5 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 55 3.11. The structure of (Z)-3-methyl-2-pentene is a. b. *c. d. e. 3.12. The structure of (E)-3-methyl-2-pentene is *a. b. c. d. e. 3.13. The correct name for CH3 CH3 CH3 CH CH C CH CH3 CH2CH3 is a. 2-methyl-4-isopropyl-3-hexene. *b. 3-ethyl-2,5-dimethyl-3-hexene. c. 2,5-dimethyl-4-ethyl-3-hexene. d. 1-ethyl-1,2-diisopropylethene. e. 1,2-diisopropyl-1-butene. Copyright © Houghton Mifflin Company. All rights reserved. 56 PART III 3.14. The double bond in ethene is made up of a. a pi bond and a sigma bond formed by lateral overlap of two p orbitals. b. a sigma bond formed by overlap of two s orbitals and a pi bond formed by lateral overlap of two p orbitals. c. a pi bond formed by end-on overlap of two sp2 orbitals and a sigma bond formed by overlap of two s orbitals. *d. a sigma bond formed by end-on overlap of two sp2 orbitals and a pi bond formed by lateral overlap of two p orbitals. e. a pi bond formed by lateral overlap of two sp2 orbitals and a sigma bond formed by end-on overlap of two sp2 orbitals. 3.15. The triple bond in ethyne is made up of a. two pi bonds and a sigma bond, each formed by a lateral overlap of two p orbitals. b. a sigma bond formed by overlap of two s orbitals and two pi bonds, each formed by lateral overlap of two p orbitals. c. a sigma bond formed by end-on overlap of two sp2 orbitals and a pi bond formed by lateral overlap of two p orbitals. *d. two pi bonds, each formed by lateral overlap of two p orbitals, and a sigma bond formed by end-on overlap of two sp orbitals. e. two pi bonds, each formed by end-on overlap of two p orbitals, and a sigma bond formed by lateral overlap of two sp orbitals. Properties of Alkenes and Alkynes 3.16. Which of the following statements is FALSE relative to alkenes? a. the C of the carbon-carbon double bond is sp2 hybridized b. the bond angles are approximately 120° around the carbon-carbon double bond c. there is the possibility of cis/trans isomerism *d. they are less reactive than alkanes e. the bond length of the carbon-carbon double bond is shorter than that of the carbon-carbon single bond 3.17. Which of the following hydrocarbons will be the most acidic? a. pentane b. ethene *c. acetylene d. isobutane e. propylene 3.18. Which of the following statements are true about alkynes? a. they are more acidic than other hydrocarbons b. the bond angle around the carbon-carbon triple bond is 180° c. the carbon-carbon triple bond is shorter than the carbon-carbon double bond *d. all of the above are true e. none of the above are true 3.19. What is the percent s character in an sp2 hybrid orbital? a. 25% *b. 33% c. 50% d. 67% e. 75% Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 57 3.20. What is the percent s character in an sp hybrid orbital? a. 25% b. 33% *c. 50% d. 67% e. 75% Reactions of Alkenes 3.21. What would be the major product of the following reaction? CH3 + HBr ?. CH3 H 3C H 3C Br Br Br Br I II III CH3 CH2Br Br IV V a. I *b. II c. III d. IV e. V 3.22. Select the necessary reagent(s) to convert cycloheptene to cycloheptane. ? *a. H2 and Ni b. H2 O c. H2SO4 and heat d. Zn and H+ e. KOH in alcohol and heat 3.23. Select the necessary reagents to convert methylcyclopentene to 1-methylcyclopentanol. CH3 H3C OH ? *a. H2 O and H2SO4 b. Zn, H2 O c. BH3 , then H2 O2 and – OH d. O3 , then Zn, H+ e. KOH in alcohol and heat Copyright © Houghton Mifflin Company. All rights reserved. 58 PART III 3.24. What is the product for the reaction below?. CH3 CH3CH2C CH2 + HBr ?.. CH3 CH3 a. CH3CHCH2CH2Br b. CH3CHCHCH3 c. CH3CHCH CHBr. Br CH2Br CH3 *d. CH3CH2CCH3 e. none of these Br. 3.25. What is the product for the reaction below? CH2CH3 + HBr ? CH2CH3 CH2CH3 CH2CH3 a. *b. c. Br Br Br Br CH2CH2Br CHCH3 d. e. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 59 3.26. Upon ozonolysis and treatment with Zn in water, compound A yielded two moles of formaldehyde, HCHO, and 1 mole of the following molecule: O O CH3CCH2CCH3 What is the structure of A?. H CH3 CH2 O C C CH CH2. H CH2 H CH3CCH2C C C CH2 H3C H I II III CH2 CH3 CH3CCCHO CH2 H2C CH2 IV V a. I *b. II c. III d. IV e. V 3.27. What is observed when water, in the presence of sulfuric acid, is added to 2-methyl-2- pentene?. CH3 a. CH3C CHCH2CH2OH b. CH3CH2CHCHCH3 CH3 OH CH3 *c. CH3CCH2CH2CH3 d. CH3CH2CH CCH2CH3 OH CH3 CH3 e. CH3CCH2CH2CH3 OSO3H. Copyright © Houghton Mifflin Company. All rights reserved. 60 PART III 3.28. The products obtained by the acid-catalyzed hydration of methylcyclopentene and methylenecyclopentane are *a. identical. b. regioisomers. c. cis-trans isomers. d. constitutional isomers. e. conformers. 3.29. The product of the reaction sequence CH3 BH3 H2O2 OH is. CH3 CH3 CH3 OH BH2 b.. *a. c. OH CH2OH d. e. none of the above 3.30. The product of the reaction. H3C H C C + HCl H3C CH2CH3. is. Cl Cl Cl *a. (CH3)2C CH2CH2CH3 b. (CH3)2C CHCH2CH3 Cl c. (CH3)2CH CHCH2CH3 d. (CH3)2CHCH2CHCH3. H3C H Cl e. C C H3C CH2CH2Cl. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 61 3.31. The products of the following reaction sequence. H 3C H O3 Zn, H + C C H 3C CH2CH3. are. H 3C H3C H a. 2 C O *b. C O O C H 3C H3C CH2CH3. O OH OH H3C H c. C C d. H3C C C H H3C CH2CH3 CH3 CH3 H e. 2 O C CH2CH3. Reactions of Conjugated Dienes 3.32. What product(s) will be observed by the addition of one molar equivalent of Br2 to 1,3-cyclohexadiene? a. 1,2-dibromocyclohexene b. 3,4-dibromocyclohexene c. 1,3-dibromocyclohexene d. 3,6-dibromocyclohexene *e. both b and d Copyright © Houghton Mifflin Company. All rights reserved. 62 PART III 3.33. The Diels-Alder reaction is very important in the synthesis of six-membered rings. What six- membered ring is produced with the following reaction? O CH3CH CHCH CHCH3 H2C CHCCH3 ?. CH3 O CH3 CH2CHO CH2CCH3. O a. b. c. CH3 CH3 CH3 CH3 O CH3 CCH3 CCH3 *d. e. O H3C CH3. 3.34. The product of addition of two moles of HBr to 1,4-pentadiene is a. 2,2-dibromopentane. *b. 2,4-dibromopentane. c. 1,5-dibromopentane. d. 3,3-dibromopentane. e. 1,4-dibromopentane. 3.35. The products obtained by adding 1 mole of HBr to 2,4-hexadiene are a. 4-bromo-2-hexene and 5-bromo-2-hexene. b. 3-bromo-2-hexene and 4-bromo-2-hexene. c. 4-bromo-2-hexene and 2-bromo-4-hexene. d. 2-bromo-3-hexene and 3-bromo-2-hexene. *e. 2-bromo-3-hexene and 4-bromo-2-hexene. Reactions of Alkynes 3.36. The product of the reaction. CH3CH2C CH + 2 Br2. is. Br Br a. C C b. CH3CH2CBr2CH3. CH3CH2 H Br H *c. CH3CH2CBr2CHBr2 d. C C CH3CH2 Br e. CH3CH2CHBrCH2Br. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 63 3.37. What type of compound is prepared by adding water to acetylene (C2 H2 ) in the presence of sulfuric acid and mercuric sulfate? *a. aldehyde b. ketone c. carboxylic acid d. ester e. ether 3.38. The product of the reaction NaNH2 CH3CH2C CH in liquid NH3 is. a. CH3CH2C CH2 *b. CH3CH2C C Na Na c. CH3CH2C CH2 d. CH3CH2CH CHNH2. NH2 e. CH3CH2C CHNH2 Na. Reactions and Nomenclature 3.39. What is the name of the product formed from the following reaction? CCl4 + Br2 ? a. bromocyclopentane b. 1,1-dibromocyclopentane *c. 1,2-dibromocyclopentane d. 2,2-dibromocyclopentane e. 1,1-dibromocyclopentene 3.40. Addition of H2 to 2-butyne in the presence of the Lindlar’s catalyst will produce: a. butane b. 1-butene *c. cis-2-butene d. trans-2-butene e. isobutylene 3.41. What alkene is required to make 3-methyl-1-butanol using the hydroboration-oxidation reaction? a. 1-butene b. 2-butene *c. 3-methyl-1-butene d. 2-methyl-2-butene e. 2-methyl-1-butene Copyright © Houghton Mifflin Company. All rights reserved. 64 PART III 3.42. What is the final product of adding 1 mole of each reactant in the following sequence? HCl HBr CH3C CH ? a. propyl chloride b. propyl bromide c. 1-bromo-2-chloropropane *d. 2-bromo-2-chloropropane e. 2,2-dibromopropane 3.43. Which of the following alkenes is needed to prepare 3-cyclohexyl-1-propanol via a hydroboration-oxidation reaction? CH2CH2CH2OH 3-cyclohexyl-1-propanol a. cyclohexene b. vinyl cyclohexane *c. allyl cyclohexane d. propyl cyclohexene e. 1- octene 3.44. Upon ozonolysis which alkene will give only acetone, (CH3 )2C=O? *a. 2,3-dimethyl-2-butene b. 2,2-dimethyl-2-butene c. 3-hexene d. 2-methyl-2-pentene e. 2-methyl-3-hexene 3.45. What is the name of the alkene produced by treating 2-butyne with 1 mole of Br2? a. 1,2-dibromo-1-butene b. 2,3-dibromo-1-butene *c. trans-2,3-dibromo-2-butene d. 2,3-dibromo-1-butene e. cis-1,4-dibromo-2-butene Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 65 Reaction Equilibrium and Reaction Rates 3.46. Examine the following reaction energy diagram for the reaction A + B C + D Ea Ea Energy A + B !H C + D Reaction Coordinate Which of the following statements are true? 1. The reaction is exothermic. 2. The reaction occurs in one step. 3. The first step is the rate-determining step. 4. The reaction is endothermic. 5. If the reaction is heated, the reaction rate will increase. a. 1, 2, and 5 *b. 1, 3, and 5 c. 2 and 4 d. 3, 4, and 5 e. 3 and 4 3.47. Which of the following statements about chemical reactions are true? 1. Exothermic reactions occur at a rapid rate. 2. The products of exothermic reactions are lower in energy than the reactants. 3. Exothermic reactions give off heat. 4. The products of endothermic reactions are lower in energy than the reactants. a. 3 b. 1, 2, and 3 c. 1, 3, and 4 *d. 2 and 3 e. 2 Reaction Mechanisms 3.48. Markovnikov addition of HCl to propene involves: a. initial attack by the chloride ion b. initial attack by the chlorine atom c. isomerization of 1-chloropropane d. formation of a propyl cation *e. formation of an isopropyl cation 3.49. What type of carbocation will form from the addition of a H+ to 2-methylpropene? + a. H3C b. 1° c. 2° *d. 3° e. allyl Copyright © Houghton Mifflin Company. All rights reserved. 66 PART III 3.50. Cyclohexene is treated with cold dilute KMnO4. What is the spatial arrangement of the hydroxyls on the resulting cyclohexane ring? *a. cis b. trans c. eclipsed d. both axial e. both equatorial 3.51. The first step in the free radical mechanism for the preparation of polyethylene is: a. formation of a stable carbocation b. formation of a stable carbanion *c. heating an organic peroxide to break the O–O bond d. decoupling of the free radicals e. propagation of the free radicals 3.52. Polyethylene is usually produced by a. an ionic electrophilic addition reaction. b. heating ethylene to 1000oC. c. cationic polymerization. *d. a free-radical chain reaction. e. epoxidation. Miscellaneous 3.53. Which of the following reagents can be used to distinguish an alkene from an alkane? a. Zn, H+ b. H2 O c. Cl2, hν *d. Br2 , CCl4 e. O2 , heat 3.54. What is/are the final product(s) in the following multistep synthesis? 1) 1 mol Br2 ? 2) H2, Pt Br. Br Br Br Br Br. I II III a. I b. II c. III *d. I and II e. all are produced Copyright © Houghton Mifflin Company. All rights reserved. Chapter 4  Chapter 4 Aromatic Compounds Nomenclature and Structural Formulas of Aromatic Compounds 4.1. The structure of chlorobenzene is correctly represented by: Cl Cl a. *b. c. Cl CH2Cl CH2Cl d. e. 4.2. Which of the following structures accurately represents toluene? *a. b. c. CH3 OH NH2. d. e. CO2H OCH3. 4.3. The name of the following molecule is: CH CH2 a. toluene b. ethylbenzene c. cumene *d. styrene e. anisole 4.4. What dibromobenzene can form only one tribromobenzene? a. o-dibromobenzene b. m-dibromobenzene *c. p-dibromobenzene d. cumene e. styrene 67 Copyright © Houghton Mifflin Company. All rights reserved. 68 PART III 4.5. Using the following monosubstituted benzene, which position would be ortho to X?. X 1 6 2 5 3 4. a. 1 *b. 2 c. 3 d. 4 e. 5 4.6. Which of the following molecules is m-nitrophenol? CH3 OH CH3 a. b. c. NO2. NO2 NO2 OH NO2 *d. e. NO2 NH2 4.7. What is the name of the following molecule? PhCH2CH2CH=CH2 a. styrene *b. 4-phenyl-1-butene c. 1-phenyl-3-butene d. 3-benzyl-1-propene e. allylbenzene 4.8. Which name(s) of the following molecule is/are incorrect? CH CH2 a. styrene b. vinylbenzene *c. ethylbenzene d. phenylethene e. a and b 4.9. How many dinitrobenzoic acids are possible? a. 4 b. 5 *c. 6 d. 7 e. 8 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 69 4.10. Which of the following names represents more than one compound? *a. dichlorobenzene b. 2-bromophenol c. o-nitrobenzaldehyde d. 2,4,6-trinitrotoluene e. cumene 4.11. How many different trisubstituted products are possible from the nitration of m-xylene? a. 1 b. 2 *c. 3 d. 4 e. 5 4.12. Which position would be meta to X?. X 1 6 2 5 3 4. a. 1 b. 2 *c. 3 d. 4 e. 6 4.13. What is the correct name for the following molecule?. Br CH2. a. o-bromobenzyl b. biphenyl bromide c. 2-bromodiphenylpropane d. bromobenzylbenzene *e. o-benzylbromobenzene 4.14. Which alkylbenzene, C9 H12, when nitrated can yield only one mononitro product? CH3 CH3 CH3 a. b. *c. CH3 H3C CH3 CH3 H3C CH3 CH2CH2CH3 e. d. Copyright © Houghton Mifflin Company. All rights reserved. 70 PART III 4.15. The correct name for. CH3 Cl Br is a. 2-chloro-4-bromotoluene. b. o-chloro-p-bromotoluene. c. 1-bromo-3-chloro-4-methylbenzene. *d. 4-bromo-2-chlorotoluene. e. m-chlorobromotoluene. 4.16. The structural formula for m-chlorobenzoic acid is a. Cl COOH b. CH3 Cl c. COOH *d. COOH Cl Cl e. Cl CH3 Aromaticity, Resonance, and Properties of Aromatic Compounds 4.17. Which of the following statements about benzene is FALSE? a. the molecule is planar and each carbon is at a corner of regular hexagon b. there are two resonance structures of equivalent energy c. the bond angles are all 120º and the bond lengths are all 1.39Å *d. the typical mechanism by which reactions occur is by addition e. each carbon in the benzene ring is sp2 hybridized 4.18. Which statement about benzene is TRUE? a. All six hydrogens in benzene are chemically equivalent. b. Benzene decolorizes bromine solutions. c. The molecule is planar, and each carbon is at the corner of a regular hexagon. *d. Both a and c are true. e. Both b and c are true. Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 71 Mechanism of Electrophilic Aromatic Substitution 4.19. Which of the following is NOT an electrophile in an electrophilic aromatic substitution reaction? + a. NO2 b. Clδ+--δ – Cl--FeCl3 *c. CH3OH d. SO3 e. all are 4.20. In the mechanism for the nitration of benzene, what is the function of H2SO4 ? a. to act solely as a solvent *b. to donate a proton to HNO3 c. to accept a proton from HNO3 d. to generate heat for reaction to occur e. to protonate the benzene ring 4.21. The predominant intermediate in electrophilic nitration of toluene is. CH3 CH3 CH3 a. *b. c. O2N O2N H O2N H H. CH3 CH3 d. e. O2N NO2 O2N H. Copyright © Houghton Mifflin Company. All rights reserved. 72 PART III 4.22. The predominant intermediate in the nitration of benzenesulfonic acid is. SO3H SO3H SO3H H a. b. c. NO2. NO2 H O2N H SO3H SO3H *d. e. NO2 NO2 H H. Directing Groups and Ring Activation 4.23. Which of the following groups is a meta director? a. –Cl *b. –CHO c. –OCH3 d. –OH e. –Ar 4.24. In electrophilic aromatic substitution reactions, which of the following molecules are considered to be less reactive than benzene?. CO2H CH3 OCH3 *a. b. c. OH d. e. 4.25. Which of the following groups are ortho, para-directing? a. —CO2CH3 b. —CONH2 c. —SO3 H + d. NH(CH3 )2 *e. —SCH3 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 73 4.26. Among the following groups, which ones are meta-directing? 1. –Cl 2. –NO2 3. –SO3 H 4. –CH3 5. –COCH3 a. 1 and 4 b. 1, 2 and 3 *c. 2, 3 and 5 d. 2 and 5 e. 1 and 2 4.27. Which of the following molecules is the most reactive toward electrophilic aromatic substitution?. NO2 NO2 a. b. c. CH3 CO2H. OH *d. e. NH2 + NH3. 4.28. Which group is both ortho, para-directing and ring-deactivating? *a. –Br b. –Ar c. –NO2 d. –CHO e. –OCH3 4.29. The relative rates of nitration of CH3 H3C CH3 SO3H. 1. 2. 3.. 4. CH3 are a. 1 > 2 > 3 > 4 b. 4 > 2 > 1 > 3 c. 2 > 1 > 4 > 3 d. 3 > 4 > 2 > 1 *e. 3 > 2 > 1 > 4 Copyright © Houghton Mifflin Company. All rights reserved. 74 PART III 4.30. The only group among the following that is m-directing is. O O a. O C R b. Cl *c. C OR. d. C(CH3)3 e. N(CH3)2. 4.31. Among the following groups, which ones are o,p-directing?. 1. OCH3 2. NO2 3. Br 4. CN 5. CH2CH3.. *a. 1, 3, and 5 b. 1 and 5 c. 2 and 4 d. 2, 3, and 4 e. 1 and 3 Reactions of Benzene and Substituted Benzenes 4.32. Which electrophile is used to make acetophenone from benzene? + + + +.. a. CH3 *b. CH3CO c. SO3 d. NO2.. e. CH3CH2 4.33. The name of the product of the following reaction is: H2SO4 + HNO3 ? a. benzenesulfonic acid b. aniline c. benzoic acid *d. nitrobenzene e. anisole 4.34. If p-nitrophenol is treated with chlorine in the presence of AlCl3, the only trisubstituted product observed is: *a. 2-chloro-4-nitrophenol b. 3-chloro-4-nitrophenol c. 3-chloro-5-nitrophenol d. 4-chloro-2-nitrophenol e. 4-chloro-3-nitrophenol 4.35. What is the name of the major product from the following sequence of reactions? 1) SO3, H2SO4 ? 2) NaOH, 200oC a. aniline b. anisole c. benzoic acid *d. phenol e. toluene Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 75 4.36. The expected product from the following reaction is: CH3 AlCl3 + CH3CH2Cl ? H3C. CH3 CH3 CH3 CH2CH3 a. b. *c. CH2CH3. CH2CH3 CH3 CH2CH3 CH2CH3 CH3 d. e. CH3 CH3. CH3 4.37. What is the final product of the following reaction sequence? 1) CH2 + CH2, H ?. 2) KMnO4,. OH CH CH2 CHCH3 CO2H. a. b. *c. CH2CH3 CH2CO2H d. e. Copyright © Houghton Mifflin Company. All rights reserved. 76 PART III 4.38. The predominant product from sequential nitration and bromination of benzenesulfonic acid is. Br SO3H Br *a. b. HO3S NO2 NO2 O2N SO3H O2N c. d. Br HO3S SO3H Br NO2 e. Br. 4.39. The predominant product from the sequential bromination and nitration of benzene is: Br NO2 Br a. b. c. NO2 Br Br Br *d. e. NO2 NO2 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 77 4.40. What is the product of the following reaction? CH3 O AlCl3 + CH3C Cl CH3. CH3 CH3 *a. b. c. CH3 C C O CH3 O CH3 CH3 CH3 Cl d. e. Al. Electrophilic Aromatic Substitution in Synthesis 4.41. What is the best sequence of reactions to synthesize m-nitrophenol? OH OH HNO3 1) HNO3, H2SO4 a. b. H2SO4 2) H2O, 1) H2SO4, OH 1) H2SO4, c. d. 2) NaOH, 200oC 2) NaOH, 200oC 3) HNO3, H2SO4 1) HNO3, H2SO4 *e. 2) H2SO4, 3) NaOH, 200oC Copyright © Houghton Mifflin Company. All rights reserved. 78 PART III 4.42. Which is the best reaction sequence to synthesize m-bromobenzenesulfonic acid from benzene?. SO3H 1) 2) Br. a. 1) Br2 , AlBr3 , 2) H2SO4 , SO3 *b. 1) H2SO4 , SO3 2) Br2 , AlBr3 c. 1) ethene, HF, 2) Br2 , AlBr3 d. 1) CH3Cl, AlCl3, 2) Br2 , AlBr3 e. 1) Br2 , AlBr3 , 2) CH3COCl, AlCl3 4.43. Which is the best sequence of reagents to use in synthesizing 2-bromo-4-nitrotoluene from benzene: a. Br2 , FeBr3; then CH3Cl, AlCl3; then HNO3 , H2SO4 b. CH3Cl, AlCl3; then Br2 , FeBr3; then HNO3 , H2SO4 *c. CH3Cl, AlCl3; then HNO3 , H2SO4; then Br2 , FeBr3 d. SO3 , H2SO4; then HNO3 , H2SO4; then Br2 , FeBr3 e. HNO3 , H2SO4; then Br2 , FeBr3; then CH3Cl, AlCl3 4.44. Which is the best reaction sequence to synthesize p-bromobenzenesulfonic acid from benzene?. SO3H 1) 2). Br *a. 1) Br2 , AlBr3 , 2) H2SO4 , SO3 b. 1) H2SO4 , SO3 , 2) Br2 , AlBr3 c. 1) CH3Cl, AlCl3, 2) Br2 , AlBr3 d. 1) Br2 , AlBr3 , 2) CH3COCl, AlCl3 e. 1) HBr, ethane, 2) H2SO4 , SO3 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 79 Polycyclic Aromatic Hydrocarbons 4.45. A common polycyclic aromatic hydrocarbon is named naphthalene. What is the structure of naphthalene? *a. b. c. d. e. 4.46. The number of possible mononitration products of anthracene is: a. 1 b. 2 *c. 3 d. 4 e. 5 4.47. The polycyclic aromatic hydrocarbon benzo[a]pyrene is a known carcinogen found in soot and tobacco smoke. What is its structure? a. b. c. d. *e. Copyright © Houghton Mifflin Company. All rights reserved. Chapter 5  Chapter 5 Stereoisomerism Definitions 5.1. Which of the following objects is chiral? a. socks b. pencil c. cross country skis d. basketball *e. shoes 5.2. Chiral molecules that have nonsuperimposable mirror images are called: *a. enantiomers b. diastereomers c. meso compounds d. stereogenic e. symmetrical 5.3. Which of the following molecules has a mirror plane of symmetry?. CH3 CH3 CH3 CH3 H Cl Cl H H Cl H Cl. C C C C C C C C Cl H Cl H Cl Cl H3C Cl CH3 CH3 CH3 CH3 1 2 3 4 a. 1 *b. 2 c. 3 d. 4 e. all of them 5.4. What is the process that separates enantiomers? a. separation b. decoupling c. resetting *d. resolution e. selective binding 5.5. A 50:50 mixture of enantiomers a. is a meso form. b. is a pair of diastereomers. *c. is a racemic mixture. d. rotates plane polarized light. e. is a pair of conformers. 5.6. The terms that best describe the isomeric relationship between staggered and eclipsed ethane are a. configurational, achiral, diastereomers. b. conformational, chiral, enantiomers. *c. conformational, achiral, diastereomers. d. configurational, chiral, enantiomers. e. conformational, achiral, enantiomers. 80 Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 81 Stereogenic Centers 5.7. Which of the molecules below has a stereogenic carbon atom? OH Br CH3 CH3CHCH3 CH3CHCHCH3 CH3CHCHCH3 CH3 CH3 1 2 3 a. 1 *b. 2 c. 3 d. 2 and 3 e. 1, 2, and 3 5.8. How many stereogenic centers are present in the following molecule? CH3 CH3 CH3CHCHCHCH2CH3 CH3 a. 1 *b. 2 c. 3 d. 4 e. 5 5.9. How many stereogenic centers are present in the following molecule?. H3C CH3 C C OH H3C CHCHCH3 OH. a. 1 *b. 2 c. 4 d. 6 e. 8 5.10. How many chiral stereoisomers can be drawn for CH 3CHClCHBrCH3 ? a. 1 b. 2 c. 3 *d. 4 e. 8 5.11. How many stereogenic carbons are in the following molecule? CH3 H3C a. 0 b. 1 *c. 2 d. 3 e. 4 5.12. How many stereoisomers can be obtained from the monobromination of butane? a. 1 *b. 2 c. 3 d. 4 e. 5 Copyright © Houghton Mifflin Company. All rights reserved. 82 PART III 5.13. How many stereoisomers with the formula CH3CHICHICH3 are possible? a. 1 b. 2 *c. 3 d. 4 e. 5 5.14. The number of stereogenic centers in progesterone is O C CH3 O progesterone (no stereochemistry shown) a. 2 b. 3 c. 4 d. 5 *e. 6 5.15. The total number of possible stereoisomers of CH3CHCHCHCH3 F Cl Br. is a. 2 b. 4 c. 6 *d. 8 e. 0 5.16. The total number of possible stereoisomers of 2-methyl-1-chlorocyclohexane is a. 2 *b. 4 c. 6 d. 8 e. 0 Optical Activity 5.17. An unknown sample is tested with a polarimeter for optical activity. The results of the test required no movement of the analyzer. What samples would give this result? a. pure enantiomer b. meso compound c. racemic mixture *d. both b and c e. none of these 5.18. An unknown sample is tested with a polarimeter for optical activity. The results of the test require movement of the analyzer. What samples would give this result? *a. pure enantiomer b. meso compound c. racemic mixture d. both b and c e. none of these 5.19. Which of the following statements about enantiomers is INCORRECT? a. they cannot be differentiated by spectra b. they have the same melting and boiling points c. the mirror image of the R stereoisomer is the S stereoisomer d. the specific rotation of each stereoisomer has the same magnitude *e. without exception the R stereoisomers will rotate light to the right Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 83 5.20. The observed rotation for 100 mL of an aqueous solution containing 1 g of sucrose, placed in a 2-decimeter sample tube, is +1.33° at 25°C. What is the specific rotation of sucrose? *a. +66.5° b. +266° c. +41.5 d. +133° e. 108° Relationships Between Stereoisomers 5.21. Which of the following molecules are the same? CH3 CH3 CH2CH3 CH3 H C Cl CH3CH2 C Cl H3C C Cl H3C C Cl CH2CH3 H H CH2CH3 1 2 3 4 a. 1 and 2 b. 3 and 4 *c. 1 and 3 d. 2 and 3 e. 2 and 4 5.22. Which of the three molecules below is the enantiomer of the following molecule? CH3 H Br I H CH3 CH3 I Br H Br Br CH3 H I I I II III *a. I b. II c. III d. there are no enantiomers e. both II and III 5.23. Which of the three molecules below is a diastereomer of the following molecule? H3C CH3 HO OH H H H3C OH H3C CH3 H3C CH3 HO H H H H OH H CH3 HO OH HO H I II III a. I b. II *c. III d. there are no diastereomers e. both I and II Copyright © Houghton Mifflin Company. All rights reserved. 84 PART III 5.24. Which of the following are achiral conformers? *a. staggered and eclipsed forms of ethane b. cis and trans-2-butene c. meso and (2R,3R)-2,3-dibromobutane d. (R) and (S)-lactic acid e. E- and Z-2-pentene 5.25. Which of the following would constitute a pair of enantiomers? a. staggered and eclipsed forms of ethane b. cis and trans-2-butene c. meso- and (2R,3R)-2,3-dibromobutane *d. (2R,3R) and (2S,3S)-tartaric acid e. none of these 5.26. The terms that best describe the relationship between (2R,3R)-2,3-butanediol and (2S,3S)-2,3-butanediol are a. configurational, achiral, diastereomers. b. conformational, chiral, enantiomers. c. conformational, achiral, diastereomers *d. configurational, chiral, enantiomers. e. configurational, achiral, enantiomers. 5.27. The terms that best describe the relationship between (2R,3S)-2-bromo-3-chlorobutane and (2R,3R)-2-bromo-3-chlorobutane are a. configurational, achiral, diastereomers. b. conformational, chiral, diastereomers. c. configurational, achiral, enantiomers. d. conformational, chiral, enantiomers. *e. configurational, chiral, diastereomers. 5.28. Which of the following statements about the pair of molecules shown below is not true? Cl Cl and H CH2CH3 H H3C CH3CH2 CH3 a. They have the same boiling point. b. One rotates plane polarized light in the opposite direction from the other. c. They have the same density. *d. One rotates plane polarized light a different number of degrees than the other. e. They are mirror images of each other. The R-S and E-Z Conventions 5.29. According to the R-S convention, which priority is correct for the following sets of groups? a. NH2 > Cl > CH3 > H *b. Cl > NH2 > CH3 > H c. Cl > CH3 > NH2 > H d. H > Cl > CH3 > NH2 e. CH3 > NH2 > Cl > H Copyright © Houghton Mifflin Company. All rights reserved.  Test Bank 85 5.30. (R)-2-chlorobutane is correctly represented by which of the following: CH3 CH3 CH3 H C Cl Cl C H H3C C Cl CH2CH3 CH2CH3 CH2CH3 I II III. CH2CH3 CH3 Cl C H Cl C CH2CH3 CH3 CH3 IV V a. I *b. II c. III d. IV e. V 5.31. Which of the following groups has the highest priority for assigning R-S absolute configuration? a. CH2=CH− b. (CH3 )2CH− *c. (CH3 )3C− d. CH3CH2− e. CH3− 5.32. The correct IUPAC name for the following molecule is: H3C Cl C C Br CH2CHCH3 CH3 *a. (E)-2-bromo-3-chloro-5-methyl-2-hexene b. (E)-2-bromo-3-chloro-5-methyl-3-hexene c. (Z)-2-bromo-3-chloro-5-methyl-3-hexene d. (Z)-2-bromo-3-chloro-5-methyl-2-hexene e. (Z)-5-bromo-4-chloro-2-methyl-4-hexene Copyright © Houghton Mifflin Company. All