Organic Chemistry, 9e (Wade)

Chapter 8 Reactions of Alkenes

1) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 1
Section: 8.3
LO: 8.1, 8.4
MCAT LO: MCAT8.1

2) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 1
Section: 8.3
LO: 8.1, 8.4
MCAT LO: MCAT8.1
3) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 1
Section: 8.3
LO: 8.1, 8.4
MCAT LO: MCAT8.1

4) HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the
peroxide serve in this reaction?
A) nucleophile
B) electrophile
C) radical chain initiator
D) acid catalyst
E) solvent
Answer: C
Diff: 2
Section: 8.3
LO: 8.1
GO: G2
MCAT LO: MCAT8.1
5) Predict the major product of the following reaction.

A)

B)

C)

D)

Answer: B
Diff: 2
Section: 8.3
LO: 8.1, 8.4
GO: G2
MCAT LO: MCAT8.1

6) Name the major product which results when HBr is added to 3-ethyl-3-hexene.
Answer: 3-bromo-3-ethylhexane
Diff: 2
Section: 8.3
LO: 8.1
GO: G2
MCAT LO: MCAT8.1
7) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.3
LO: 8.1
GO: G2
MCAT LO: MCAT8.1

8) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.3
LO: 8.1, 8.4
GO: G2
MCAT LO: MCAT8.1
9) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.3
LO: 8.1, 8.4
MCAT LO: MCAT8.1

10) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.3
LO: 8.1, 8.4
GO: G2
MCAT LO: MCAT8.1

11) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.3
LO: 8.1, 8.4
GO: G2
MCAT LO: MCAT8.1
12) Based on the relative stabilities of the intermediates involved, explain the basis for
Markovinkov's rule in the addition of hydrogen halides to alkenes.
Answer: The rate-determining step in this reaction is the production of a carbocation
intermediate. Since this step is endothermic, Hammond's postulate allows one to gauge the
relative stabilities of the transition states by comparing the relative stabilities of the carbocation
intermediates. The reaction pathway which produces the more substituted carbocation will thus
occur more rapidly.
Diff: 2
Section: 8.3
LO: 8.6
GO: G8
MCAT LO: MCAT8.3

13) Complete the following reaction and provide a detailed, step-by-step mechanism for the
process.

Answer:

Diff: 2
Section: 8.3
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

14) When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which
of the following structures are formed during the mechanism?

A)
B)

C)
D) H∙
Answer: B
Diff: 2
Section: 8.3
LO: 8.6
GO: G2
MCAT LO: MCAT8.3
15) Using any alkene as your starting material, how could you make the alkyl halide shown?

Answer:

Diff: 3
Section: 8.3
LO: 8.2, 8.7
GO: G2

16) Draw the major regioisomeric product generated in the reaction below.

Answer:

Diff: 3
Section: 8.3
LO: 8.1, 8.4
MCAT LO: MCAT8.1
17) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.3
LO: 8.1
MCAT LO: MCAT8.1

18) Draw a full and complete mechanism to account for the formation of the product in the
reaction shown below.

Answer:

Diff: 3
Section: 8.3
LO: 8.6
GO: G2
MCAT LO: MCAT8.3
19) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.3
LO: 8.1, 8.4
GO: G2
MCAT LO: MCAT8.1

20) Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.
Answer: The reaction proceeds via the addition of Br∙ to the alkene. Two competing pathways
are possible, but the transition state leading to the more substituted alkyl radical is lower in
energy. This process ultimately makes the addition anti-Markovnikov in nature.
Diff: 3
Section: 8.3
LO: 8.6
GO: G8
MCAT LO: MCAT8.3

21) When 3,6-dimethylcyclohexene is reacted with dry gaseous HBr, one of the products is 1-
bromo-1,4-dimethylcyclohexane. Provide a detailed step-by-step mechanism to explain the
formation of this product.
Answer:

Diff: 3
Section: 8.3
LO: 8.6
GO: G2
MCAT LO: MCAT8.3
22) Which radical is an intermediate in the following reaction?

A)

B)

C)

D)

Answer: A
Diff: 3
Section: 8.3
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

23) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 1
Section: 8.4
LO: 8.1, 8.3
MCAT LO: MCAT8.1
24) The mechanism for the acid-catalyzed hydration of alkenes is simply the reverse of the
mechanism by which alcohols are dehydrated using concentrated acid. This is an illustration of
the principle of ________.
Answer: microscopic reversibility
Diff: 1
Section: 8.4
LO: 8.6
MCAT LO: MCAT8.3

25) Acid catalyzed hydration (H2SO4/water/△) of an unknown compound (A) with a chemical
formula C6H12, yielded a racemic mixture of product C6H13OH. Which, if any, of the
following compounds is/are possible structures for the initial compound (A)?

A) compound 1 only
B) compounds 2 and 3
C) compound 2 only
D) compounds 1 and 3
E) none of the above
Answer: E
Diff: 2
Section: 8.4
LO: 8.3
GO: G2
MCAT LO: MCAT8.1

26) Name the major alcohol product which results when 3,3-dimethylbut-1-ene is treated with
dilute acid.
Answer: 2,3-dimethyl-2-butanol
Diff: 2
Section: 8.4
LO: 8.1, 8.3
GO: G2
MCAT LO: MCAT8.1
27) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.4
LO: 8.1, 8.3
MCAT LO: MCAT8.1

28) What is the major product of the following reaction?

A)

B)

C)

D)

Answer: D
Diff: 2
Section: 8.4
LO: 8.1, 8.3
GO: G2
MCAT LO: MCAT8.1
29) Draw the major organic product(s) generated in the reaction below. Pay particular attention
to regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.4
LO: 8.3
MCAT LO: MCAT8.1

30) Which of the following intermediates is thought to occur in the mechanism by which alkenes
are hydrated in the presence of acid?
A) carbanion
B) carbocation
C) free radical
D) carbene
E) alkyne
Answer: B
Diff: 2
Section: 8.4
LO: 8.6
GO: G2
MCAT LO: MCAT8.3
31) Complete the following reaction and provide a detailed, step-by-step mechanism for the
process.

Answer:

Diff: 2
Section: 8.4
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

32) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-

B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O
Answer: B
Diff: 2
Section: 8.4
LO: 8.7
GO: G7
33) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 3
Section: 8.4
LO: 8.1, 8.3
MCAT LO: MCAT8.1

34) Treatment of an alkene with an alcohol in the presence of an acid catalyst produces an ether
as the major organic product. Provide a mechanism that shown how this product is formed.

Answer:

Diff: 3
Section: 8.4
LO: 8.6
MCAT LO: MCAT8.3
35) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.4
LO: 8.1, 8.3
GO: G2
MCAT LO: MCAT8.1

36) Which one of these alkene would be likely to experience a carbocation rearrangement when
treated with aqueous acid?

A)

B)

C)

D) None of these would undergo a rearrangement.

Answer: B
Diff: 3
Section: 8.4
LO: 8.6
GO: G2
MCAT LO: MCAT8.3
37) Provide the reagents necessary to complete the following transformation.

Answer: 1) Br2, hν
2) H2O, Δ
or
1) Br2, hν
2) NaOCH3, CH3OH
3) H3O+ or Hg(OAc)2, H2O; NaBH4
Diff: 3
Section: 8.4
LO: 8.7
GO: G7

38) Which of the following is the best reaction sequence to use if one wants to accomplish a
Markovnikov addition of water to an alkene with minimal skeletal rearrangement?
A) water + dilute acid
B) water + concentrated acid
C) oxymercuration-demercuration
D) hydroboration-oxidation
E) none of the above
Answer: C
Diff: 1
Section: 8.5
LO: 8.2
GO: G2
MCAT LO: MCAT8.1

39) What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration

sequence?
A) Markovnikov addition of H2O wherein skeletal rearrangement is promoted
B) Markovnikov addition of H2O wherein skeletal rearrangement is prevented
C) anti-Markovnikov addition of H2O wherein skeletal rearrangement is promoted
D) anti-Markovnikov addition of H2O wherein skeletal rearrangement is prevented
E) syn-hydroxylation
Answer: B
Diff: 2
Section: 8.5
LO: 8.3
GO: G2
MCAT LO: MCAT8.1
40) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.5
LO: 8.3
GO: G2
MCAT LO: MCAT8.1

41) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.5
LO: 8.3
GO: G2
MCAT LO: MCAT8.1
42) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.5
LO: 8.3
GO: G2
MCAT LO: MCAT8.1

43) Which one of these alkene would be likely to experience a carbocation rearrangement when
treated with Hg(OAc)2 in water, followed by reaction with sodium borohydride?

A)

B)

C)

D) None of these would undergo a rearrangement.

Answer: D
Diff: 3
Section: 8.4
LO: 8.6
GO: G2
MCAT LO: MCAT8.3
44) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.5
LO: 8.3
MCAT LO: MCAT8.1

45) When an alkene is subjected to treatment with Hg(OAc)2 in alcohol followed by reaction
with NaBH4, what new class of compound is formed?
A) ether
B) epoxide
C) alkane
D) syn diol
E) alkyne
Answer: A
Diff: 2
Section: 8.6
LO: 8.3
MCAT LO: MCAT8.1
46) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.6
LO: 8.3
MCAT LO: MCAT8.1

47) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol.

Answer: 1) conc. H2SO4
2) H3O+ or Hg(OAc)2, H2O followed by NaBH4
or
1) PBr3
2) NaOCH3, CH3OH
3) H3O+ or Hg(OAc)2, H2O followed by NaBH4
Diff: 2
Section: 8.6
LO: 8.7
GO: G7

48) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.6
LO: 8.3
GO: G2
MCAT LO: MCAT8.1
49) Treatment of 2-methylpropene with which of the following reaction conditions results in an
anti-Markovnikov addition product?
A) dry gaseous HBr with peroxides present
B) BH3-THF, followed by alkaline H2O2
C) aqueous Hg(OAc)2, followed by alkaline NaBH4
D) dilute H2SO4 and heat
E) both A and B
Answer: E
Diff: 1
Section: 8.7
LO: 8.3
GO: G2
MCAT LO: MCAT8.2

50) How many moles of BH3 need to be added to completely react with 1 mole of hex-1-ene?
A) 1 mole of BH3
B) 3 mole of BH3
C) 1/3 mole of BH3
D) 1/2 mole of BH3
Answer: C
Diff: 2
Section: 8.7
GO: G2

51) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.7
LO: 8.3
MCAT LO: MCAT8.1
52) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.7
LO: 8.3
MCAT LO: MCAT8.1

53) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.7
LO: 8.3
GO: G2
MCAT LO: MCAT8.1

54) Complete the following reaction by filling in the appropriate reagents.

Answer:

Diff: 2
Section: 8.7
LO: 8.2, 8.7
GO: G2
55) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-

B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O
Answer: A
Diff: 2
Section: 8.7
LO: 8.2, 8.7
GO: G2

56) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 3
Section: 8.7
LO: 8.5
MCAT LO: MCAT8.2
57) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.7
LO: 8.5
MCAT LO: MCAT8.2

58) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.7
LO: 8.5
MCAT LO: MCAT8.2

59) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

(Z)-3-hexene →
Answer:

Diff: 3
Section: 8.7
LO: 8.3
GO: G2
MCAT LO: MCAT8.2

60) Use a transition state to explain the regiochemistry of the reaction below. Make sure to
include correct partial charges.

Answer:

The boron adds to the less sterically hindered carbon. The partial positive charge ends up on the
more substituted carbon.
Diff: 3
Section: 8.7
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

61) Which of the following additions to alkenes occur(s) specifically in an anti fashion?
A) hydroboration-oxidation
B) addition of Br2
C) addition of H2
D) addition of H2O in dilute acid
E) both A and B
Answer: B
Diff: 1
Section: 8.8
LO: 8.5
GO: G2
MCAT LO: MCAT8.2

62) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 1
Section: 8.8
LO: 8.4
GO: G2
MCAT LO: MCAT8.2
63) Complete the following reaction and provide a detailed, step-by-step mechanism for the
process.

Answer:

Diff: 1
Section: 8.8
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

64) Addition of Br2 to (E)-hex-3-ene produces ________.

A) a meso dibromide
B) a mixture of enantiomeric dibromides which is optically active
C) a mixture of enantiomeric dibromides which is optically inactive
D) (Z)-3,4-dibromo-3-hexene
E) (E)-3,4-dibromo-3-hexene
Answer: A
Diff: 2
Section: 8.8
LO: 8.5
MCAT LO: MCAT8.2
65) Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at
room temperature?

A)

B)

C)

D)

E) both Band D
Answer: B
Diff: 2
Section: 8.8
LO: 8.5
MCAT LO: MCAT8.2

66) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.8
LO: 8.5
MCAT LO: MCAT8.2

67) Draw the major organic product(s) generated in the reaction below. Pay particular attention
to regio- and stereochemical detail.
Answer:

Diff: 2
Section: 8.8
LO: 8.5
MCAT LO: MCAT8.2

68) Provide a detailed, step-by-step mechanism for the reaction shown below.

Answer:

Diff: 2
Section: 8.8
LO: 8.6
MCAT LO: MCAT8.3
69) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.8
LO: 8.5
MCAT LO: MCAT8.2

70) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.8
LO: 8.5
MCAT LO: MCAT8.2

71) Consider how the I—Cl bond is polarized and predict the product which results when this
mixed halogen adds to 1-methylcyclohexene.
Answer:

Diff: 3
Section: 8.8
LO: 8.4, 8.5
MCAT LO: MCAT8.2
72) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.9
LO: 8.4, 8.5
MCAT LO: MCAT8.2

73) Predict the product of the following reaction. Include any relevant stereochemistry.

Answer:

Diff: 3
Section: 8.9
LO: 8.4, 8.5
MCAT LO: MCAT8.2
74) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.9
LO: 8.4
GO: G2
MCAT LO: MCAT8.2

75) Using any alkene as a starting material, how would you make the compound shown below?

Answer:

Diff: 3
Section: 8.9
LO: 8.7
GO: G2
76) Draw a full and complete mechanism for the following reaction.

Answer:

Diff: 3
Section: 8.9
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

77) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 1
Section: 8.10
LO: 8.4
MCAT LO: MCAT8.1

78) Both (E)- and (Z)-hex-3-ene can be treated with D2 in the presence of a platinum catalyst.
How are the products from these two reactions related to each other?
A) The (E)- and (Z)-isomers generate the same products but in differing amounts.
B) The (E)- and (Z)-isomers generate the same products in exactly the same amounts.
C) The products of the two isomers are related as constitutional isomers.
D) The products of the two isomers are related as diastereomers.
E) The products of the two isomers are related as enantiomers.
Answer: D
Diff: 2
Section: 8.10
LO: 8.4
GO: G7
MCAT LO: MCAT8.1
79) ________ is the use of an optically active reagent or catalyst to convert an optically inactive
starting material into an optically active product.
A) Asymmetric induction
B) Racemization
C) Optical reduction
D) Meso effection
E) Chiralization
Answer: A
Diff: 2
Section: 8.10

80) Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is
hydrogenated in the presence of platinum catalyst, 0.75 mol of H2 reacts with the humulene to
produce a monocyclic hydrocarbon of formula C15H30. What is the molecular formula of
humulene?
Answer: C15H24
Diff: 2
Section: 8.10
LO: 8.4
GO: G4
MCAT LO: MCAT8.1

81) Draw the major organic product(s) generated in the reaction below. Pay particular attention
to regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.10
LO: 8.4
GO: G2
MCAT LO: MCAT8.1
82) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.11
GO: G2
MCAT LO: MCAT8.1

83) One method of making a carbene uses diazomethane, CH2N2, which is zwitterionic. Draw
the Lewis Structure of diazomethane and any additional resonance structures of this compound.
Answer:

Diff: 3
Section: 8.11
LO: 1.3
GO: G7
MCAT LO: MCAT1.2

84) Complete the following reaction by filling in the necessary reagents.

Answer:

Diff: 3
Section: 8.11
LO: 8.7
GO: G2
85) Provide the reagents necessary to complete the following transformation.

Answer: 1) Br2, hν
2) NaOCH3, CH3OH
3) CH2I2, Zn(Cu)
Diff: 3
Section: 8.11
LO: 8.7
GO: G2

86) Name the compound PhCO3H and give its most common use as a reagent.
Answer: peroxybenzoic acid; an oxidizing agent which converts alkenes to epoxides
Diff: 1
Section: 8.12
LO: 8.4
GO: G2
MCAT LO: MCAT8.1

87) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.12
LO: 8.4
GO: G2
MCAT LO: MCAT8.1
88) Draw a mechanism that shows how the product is formed.

Answer:

Diff: 2
Section: 8.12
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

89) Draw the major organic product(s) generated in the reaction below. Pay particular attention
to regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.12
LO: 8.4
MCAT LO: MCAT8.1
90) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-

B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O
Answer: D
Diff: 2
Section: 8.12
LO: 8.7
GO: G2

91) Treatment of cyclopentene with peroxybenzoic acid ________.

A) results in oxidative cleavage of the ring to produce an acyclic compound
B) yields a meso epoxide
C) yields an equimolar mixture of enantiomeric epoxides
D) gives the same product as treatment of cyclopentene with OsO4
E) none of the above
Answer: B
Diff: 3
Section: 8.12
LO: 8.4
GO: G2
MCAT LO: MCAT8.1

92) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.12
LO: 8.4
MCAT LO: MCAT8.1
93) Which of the following steps would successfully complete the following reaction?

A) I only
B) II & III
C) I & IV
D) I, II, & IV
Answer: A
Diff: 3
Section: 8.12
LO: 8.7
GO: G2

94) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.13
LO: 8.4
MCAT LO: MCAT8.1
95) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-

B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O
Answer: E
Diff: 2
Section: 8.13
LO: 8.7
GO: G2

96) Provide the structure of the major organic product of the reaction below.

Answer:

Diff: 3
Section: 8.13
LO: 8.4
MCAT LO: MCAT8.1
97) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.13

98) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.13
LO: 8.4
MCAT LO: MCAT8.1
99) Provide a detailed, step-by-step mechanism for the reaction shown below.

Answer:

Diff: 3
Section: 8.13
LO: 8.6
GO: G2
MCAT LO: MCAT8.3

100) A reaction of an unknown alkene with MCPBA in dichloromethane followed by work-up

with H2O/H+ yielded, as the major product, a racemic mixture of (2S,3S) and (2R,3R)-3-
methylpentan-2,3-diol. What is the specific structure of the alkene used in the reaction?
A) (Z)-3-methylpent-2-ene
B) (E)-3-methylpent- 2-ene
C) 2-methylpent-2-ene
D) 2,3-dimethylbut-2-ene
E) none of the above
Answer: A
Diff: 3
Section: 8.13
LO: 8.4
GO: G2
MCAT LO: MCAT8.2
101) Provide the reagents necessary to complete the following transformation.

Answer: 1) NaOCH3, CH3OH

2) MCPBA or CH3CO3H
3) H3O+ or -OH
Diff: 3
Section: 8.13
LO: 8.7
GO: G7

102) Which of the following additions to alkenes occur(s) specifically in an syn fashion?
A) dihydroxylation using OsO4, H2O2
B) addition of H2
C) hydroboration
D) addition of HCl
E) A, B, and C
Answer: E
Diff: 1
Section: 8.14
LO: 8.5
GO: G2
MCAT LO: MCAT8.2

103) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.14
LO: 8.5
MCAT LO: MCAT8.2
104) Provide the major organic product of the following reaction.

Answer:

Diff: 2
Section: 8.14
LO: 8.5
MCAT LO: MCAT8.2

105) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.14
LO: 8.5
MCAT LO: MCAT8.2
106) Draw the major organic product(s) generated in the reaction below. Pay particular attention
to regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.14
LO: 8.5
MCAT LO: MCAT8.2

107) Provide the reagents necessary to complete the following transformation.

Answer: 1) NaOCH3, CH3OH

2) OsO4, H2O2 or cold, dilute KMnO4, -OH
Diff: 2
Section: 8.14
LO: 8.7
GO: G7
108) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-

B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O
Answer: C
Diff: 2
Section: 8.14
LO: 8.7
GO: G7

109) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.14
LO: 8.5
MCAT LO: MCAT8.2

110) Give the structure of the alkene which would yield the following products upon ozonolysis-
reduction.

CH3CH2CH2CH2CHO + CH2O
Answer: CH3CH2CH2CH2CH CH2
Diff: 1
Section: 8.15
LO: 8.8
GO: G2
111) Give the structure of the alkene which would yield the following products upon ozonolysis-
reduction.

CH3COCH3 + CH3CH2CHO
Answer: (CH3)2C CHCH2CH3
Diff: 1
Section: 8.15
LO: 8.8
GO: G2

112) An unknown compound with empirical formula C3H5 was treated with Br2/CCl4. The
bromine solution went from orangish/red to clear immediately at room temperature. Upon
treatment with O3 followed by work-up with dimethylsulfide the following products were
identified. From the information provided what is/are the most likely structure(s) for this
unknown compound.

A)

B)

C)

D)

E) both A and D
Answer: A
Diff: 2
Section: 8.15
LO: 8.7
GO: G2

113) How many moles of carbon dioxide are generated when one mole of the compound shown
is treated with warm, concentrated KMnO4?

A) 1
B) 2
C) 3
D) 4
E) 8
Answer: C
Diff: 2
Section: 8.15
LO: 8.8

114) Provide the major organic product of the reaction below.

Answer:

Diff: 2
Section: 8.15
LO: 8.4
GO: G2
MCAT LO: MCAT8.1

115) Ozonolysis-reduction of an unknown alkene gives equal amounts of CH3CH2CHO and

CH3CH2CH2CHO. Name the unknown alkene.
Answer: Either (E)- or (Z)-3-heptene
Diff: 2
Section: 8.15
LO: 8.8
116) Provide the major organic product of the following reaction.

Answer:

Diff: 2
Section: 8.15
LO: 8.4
GO: G2
MCAT LO: MCAT8.1

117) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1
118) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 2
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1

119) β-Ocimene is a natural product with a pleasant odor. Based on the information below,
deduce the structure of β-ocimene.

Answer:

Diff: 2
Section: 8.15
LO: 8.8
GO: G5

120) What alkene, which contains no oxygen atoms and a single C C, will give
CH3CO(CH2)4CHO upon treatment with OsO4 followed by cleavage with periodic acid?
Answer: 1-methylcyclohexene
Diff: 2
Section: 8.15
LO: 8.8
121) Complete the following reaction by filling in the necessary reagents.

Answer: 1) O3
2) DMS
Diff: 2
Section: 8.15
LO: 8.7
GO: G2

122) Predict the structure of the products resulting from the reaction between limonene, a natural
terpene found in citrus fruit, and ozone, followed by work up with dimethyl sulfide.

Answer:

Diff: 3
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1
123) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1

124) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1
125) Draw the major organic product generated in the reaction below. Pay particular attention to
regio- and stereochemical detail.

Answer:

Diff: 3
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1

126) Provide the structure of the product which results when the alkene below is treated with O3
followed by (CH3)2S.

Answer:

Diff: 3
Section: 8.15
LO: 8.4
MCAT LO: MCAT8.1
127) Which of the following compounds is (are) appropriate to promote the cationic
polymerization of isobutylene?
A) H2SO4
B) BF3
C) ROOR
D) NaOH
E) both H2SO4 and BF3
Answer: E
Diff: 2
Section: 8.16

128) When isobutylene [CH2 C(CH3)2] is treated with BF3, polyisobutylene is formed. Provide
a step-by-step mechanism for this polymerization reaction.
Answer:

Diff: 2
Section: 8.16
LO: 8.6
MCAT LO: MCAT8.3

129) Why can methyl acrylate (H2C CHCO2CH3) be polymerized through anionic
polymerization?
Answer: The intermediate carbanion and the transition state leading to it are stabilized by the
electron-withdrawing capacity of the carbonyl group.
Diff: 2
Section: 8.16

130) What cyclic products results when 1,8-nonadiene is treated with Grubbs catalyst?
Answer: cycloheptene
Diff: 2
Section: 8.17
LO: 8.9

131) What cyclic product results when octa-1,7-diene is subjected to ring closing metathesis?
Answer: cyclohexene
Diff: 2
Section: 8.17
LO: 8.9
GO: G8
132) What is the expected product of the following reaction?

A)

B)

C)

D)

Answer: A
Diff: 2
Section: 8.17
LO: 8.9
GO: G2

133) Draw the product when trans-hex-3-ene reacts with MMPP in ethanol.
Answer:

Diff: 1
Section: 8.13
LO: 8.4
MCAT LO: MCAT8.1
134) What alkene, which contains no oxygen atoms and a single C C, will give benzophenone
(shown below) as the only product upon treatment with O3 followed by reaction with dimethyl
sulfide.

Answer:

Diff: 2
Section: 8.15
LO: 8.8
GO: G2