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Organic Chemistry
Carey/Giuliano
8th edition
Chapter 5
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Question 1
Name the alkene below according to the
IUPAC system.
A) 2-bromo-5-heptane
B) 6-bromo-2-heptene
C) 2-bromo-5-heptene
D) 5-bromo-2-heptene
Question 2
How many alkenes will produce 3-ethylpentane
on catalytic hydrogenation?
A) 2
B) 3
C) 4
D) 5
Question 3
What is the major product of the dehydration of
2-methylcyclohexanol?
A) 1-methylcyclohexene
B) 2-methylcyclohexene
C) 3-methylcyclohexene
D) cyclohexene
Question 4
The major product of the dehydration of 1phenyl-2-propanol is
A)
B)
C)
D)
Question 5
Which alkene can have cis/trans stereoisomers?
A)
B)
C)
D)
Question 6
Of the compounds with the formula C3H5Cl,
which one has cis/trans isomers?
A) 1-chloropropene
B) 2-chloropropene
C) 3-chloropropene
D) all of them
Question 7
Assign the configuration of the alkenes below
as Z or E, respectively.
A) E,E
B) E,Z
C) Z,Z
D) Z,E
Question 8
Rank the following alkenes in order of
decreasing heat of combustion:
A) 3 > 1 > 2
B) 2 > 3 > 1
C) 1 > 2 > 3
D) 2 > 1 > 3
Question 9
The dehydration of 2-methyl-2-propanol cannot
be accomplished by using which of the
following reagents?
A) H2SO4
B) H3PO4
C) HCl
D) KHSO4
Question 10
What is the major product in the reaction of 2methyl-2-butanol with H2SO4 at 80°C?
A)
B)
C)
D)
Question 11
The reaction of 2-bromobutane with
KOCH2CH3 in ethanol produces trans-2butene. If the concentration of both
reactants is doubled, what would be the
effect on the rate of the reaction?
A) halve the rate
B) double the rate
C) quadruple the rate
D) no effect on the rate
Question 12
Which would react with KOCH2CH3 in ethanol
faster?
A) cis-2-tert-butylcyclohexyl bromide
B) trans-2-tert-butylcyclohexyl bromide
Question 13
Which would react with KOC(CH3)3/(CH3)3COH
faster?
A) cis-3-tert-butylcyclohexyl bromide
B) trans-3-tert-butylcyclohexyl bromide
Question 14
How many alkenes would you expect to be
formed from the E2 elimination of
3-bromo-2-methylpentane?
A) 2
B) 3
C) 4
D) 5
Question 15
Of the isomeric alcohols having the molecular
formula C5H12O, which one will undergo
acid-catalyzed dehydration most readily?
A) 2-pentanol
B) 2-methyl-1-butanol
C) 2-methyl-2-butanol
D) 3-methyl-2-butanol
Question 16
The heat of hydrogenation of cis-2-pentene is
117 kJ/mol. For which one of the following
alkenes is the heat of hydrogenation 126
kJ/mol?
A) 1-pentene
B) trans-2-pentene
C) 2-methyl-1-butene
D) 2,3-dimethyl-2-butene
Question 17
The molecular formula of β-Carotene is C40H56.
On catalytic hydrogenation, β-carotene is
converted to a saturated hydrocarbon of
molecular formula C40H78. How many rings
does β-carotene contain?
A) none
B) one
C) two
D) three
Question 18
Which one of the following best describes a
mechanistic feature of the reaction of
3-bromopentane with sodium ethoxide?
A) The reaction occurs in a single step which
is bimolecular.
B) The reaction occurs in two steps, both of
which are unimolecular.
C) The rate-determining step involves the
formation of the carbocation (CH3CH2)2CH+.
D) The carbon-halogen bond breaks in a rapid
step that follows the rate-determining step.
Question 19
Which of the following statements is false?
A) tert-Butyl alcohol reacts with sodium faster
than 1-butanol.
B) tert-Butyl alcohol reacts with hydrogen
bromide faster than sec-butyl alcohol.
C) tert-Butyl alcohol undergoes acid-catalyzed
dehydration faster than sec-butyl alcohol
does.
D) tert-Butyl alcohol undergoes E2 elimination
faster than tert-butyl fluoride does.
Question 20
The Zaitsev rule can be used to predict the
major product of which one of the following
reactions?
A) 2-methylbutane + Cl2 (heat)
B) 2-methyl-2-butanol + Na
C) 2-methyl-2-butanol with HCl
D) 2-bromo-2-methylbutane + NaOCH2CH3
in ethanol (heat)
Question 21
Which reaction would be most likely to proceed
by an E1 mechanism?
A) 2-chloro-2-methylbutane + NaCH2CH3 in
ethanol (heat)
B) 1-bromo-2-methylbutane + KOC(CH3)3 in
DMSO
C) 2-bromo-2-methylbutane in ethanol
(heat)
D) 2-methyl-2-butanol + K
Question 22
Which one of the following groups has the
highest rank when precedence is assigned
according to the Cahn-Ingold-Prelog system?
A) -CH2Cl
B) -CH=O
C) -C(CH3)3
D) CH2NH2
Question 23
How many alkenes, including stereoisomers,
contain a tert-butyl group and have the
molecular formula C7H14?
A) 3
B) 4
C) 5
D) 6
Answer Key – Chapter 5
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B
A
A
C
D
A
A
D
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B
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B
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C
A
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C
A
B