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Organic Chemistry 9th Edition Carey Test Bank 1
Organic Chemistry 9th Edition Carey Test Bank 1
1. Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why?
A) The double bond is much stronger and thus more difficult to rotate.
B) Overlap of the two 2p orbitals of the bond would be lost.
C) The shorter bond length of the double bond makes it more difficult for the
attached groups to pass each other.
D) Overlap of the sp2 orbitals of the carbon-carbon bond would be lost.
Ans: B
A) 2,5-dimethyl-1-hexene C) 2,5-dimethyl-2-hexene
B) 1,4-dimethyl-1-hexene D) 2,5-dimethyl-5-hexene
Ans: A
A) 2-methyl-3-propyl-2-pentene C) 4-ethyl-5-methyl-4-hexene
B) 2,3-dimethyl-2-hexene D) 4-methyl-3-propyl-3-pentene
Ans: B
Page 58
Chapter 5: Structure and Preparation of Alkenes – Elimination Reactions
A) 3-ethyl-8-methyl-3-nonene C) 1,1-diethyl-6-methyl-3-heptene
B) 7-ethyl-2-methyl-6-nonene D) 3-ethyl-7-isopropyl-3-octene
Ans: A
5. How many isomeric alkenes of formula C4H8, including stereoisomers, are possible?
A) two B) three C) four D) five
Ans: C
6. How many isomeric alkenes of formula C5H10, including stereoisomers, are possible?
A) three B) four C) five D) six
Ans: D
A) 3-bromo-2-methylcyclohexene C) 6-bromo-1-methylcyclohexene
B) 1-bromo-2-methyl-2-cyclohexene D) 2-bromo-1-methylcyclohexene
Ans: C
A) 3-ethyl-propyl-1-heptene C) 4,6-diethyl-1-octene
B) ethyl-3-vinyloctane D) 3,5-diethyl-1-octene
Ans: D
Page 59
Chapter 5: Structure and Preparation of Alkenes – Elimination Reactions
I. CH3CH2CH CHCH2CH3
A) (E)-3-bromo-1-fluoro-2-methylpropene
B) (Z)-3-bromo-1-fluoro-2-methylpropene
C) (E)-1-bromo-3-fluoro-2-methylpropene
D) (Z)-1-bromo-3-fluoro-2-methylpropene
Ans: A
12. Which of the following C6H12 isomers has the highest heat of combustion?
A) 1-hexene B) trans-3-hexene C) cis-3-hexene D) 2-methyl-2-pentene
Ans: A
13. Identify the major organic product expected from the acid-catalyzed dehydration of 2-
methyl-2-pentanol.
A) 2-methyl-1-pentene C) 3-methyl-1-pentene
B) 2-methyl-2-pentene D) cis-3-methyl-2-pentene
Ans: B
14. Which alcohol below would undergo acid-catalyzed dehydration most readily?
A) A B) B C) C D) D
Ans: D
Page 60
Chapter 5: Structure and Preparation of Alkenes – Elimination Reactions
15. What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-
2-propanol?
A) A B) B C) C D) D
Ans: C
Page 61
Chapter 5: Structure and Preparation of Alkenes – Elimination Reactions
18. Which of the following expressions is the experimentally observed rate law for an E2
reaction of an alkyl halide?
A) rate = k[RX]
B) rate = k[RX][base]
C) rate = k[RX]2
D) rate = k[base]
Ans: B
19. Which of the following most readily undergoes an E2 reaction with sodium ethoxide
(NaOCH2CH3)?
A) (CH3)3CF B) (CH3)3CCl C) (CH3)3CBr D) (CH3)3CI
Ans: D
20. How many isomeric alkenes are possible, including stereoisomers, in the following
reaction?
Page 62
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