CH 8

Chapter Eight
MULTIPLE CHOICE QUESTIONS
Topic: General Information

Section: 8.1
Difficulty Level: Medium
1. The thermodynamic parameters at 298 K for the following reaction are given below.
gas phase
CH2=CH2 + HCl CH3CH2Cl H = -64.9 kJ mol-1
S = -131 J K-1 mol-1
G = -25.8 kJ mol-1
Which of the following statements is true of the reaction?
A) Both H and S favor product formation.
B) Neither H nor S favors product formation.
C) The entropy term is unfavorable but the formation of ethyl chloride is favored.
D) The entropy term is favorable but the formation of ethyl chloride is not favored.
E) The sign of G indicates that the reaction cannot occur as written.
Ans: C
Topic: Reaction Products

Section: 8.1A
Difficulty Level: Easy
2. The interaction of the bond of an alkene with an electrophile can initially result in the
formation of a species termed a complex. Which of these cannot combine with an
alkene to form a complex?
A) H+
B) NH3
C) Ag+
D) Hg2+
E) BF3
Ans: B
201
Section: 8.2
3. Markovnikov addition of HI to 2-methyl-2-butene involves:

A) initial attack by an iodide ion.
B) initial attack by an iodine atom.
C) isomerization of 2-iodo-2-methylbutene.
D) formation of a carbocation at C-2.
E) formation of carbocation at C-3.
Ans: D

Section: 8.2
4. What is the major product for the following reaction?
HI
A)
I
B)
+ enantiomer
I
C)
+ enantiomer
I
D) I
+ enantiomer
E) I
+ enantiomer
Ans: A
202
Section: 8.2
5. What would be the major product of the following reaction?

HCl
Cl Cl
Cl Cl
I II III
Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
203
Section: 8.2
6. Treating 1-methylcyclohexene with HCl would yield primarily which of these?

H3C H3C H3C
Cl
Cl Cl
I II III
H3C Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Section: 8.2
7. How many compounds are possible from the addition of bromine to CH2=CHCH2CH3
(counting stereoisomers separately)?
A) One
B) Two
C) Three
D) Four
E) Five
Ans: B
204
Section: 8.2
8. (R)-3-Chloro-1-butene reacts with HCl by Markovnikov addition, and the products are
separated by gas chromatography. How many total fractions would be obtained and
how many would be optically active?
A) One optically active fraction only
B) One optically active fraction and one optically inactive
C) Two optically active fractions
D) One optically active fraction and two optically inactive
E) Two optically active fractions and one optically inactive
Ans: B

Section: 8.2
HBr
A)
+ enantiomer
Br
B)
+ enantiomer
Br
C) Br
+ enantiomer
D)
+ enantiomer
Br
E) More than one of the above
Ans: C
205
Section: 8.2
HCl
A)
Cl
B)
Cl
C)
Cl
D)
Cl
E) Cl
Ans: E
206
Section: 8.2
HBr
A)
Br
B) Br
C)
+ enantiomer
Br
D) Br

Ans: D
207
Section: 8.2
12. What product would you expect from addition of deuterium chloride to 2-cyclohexyl-4-
methyl-2-pentene?
Cl D
D
D H Cl
Cl
I II III
Cl
D D
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B

Section: 8.2
13. Addition of hydrogen chloride to the following molecule would produce:

HCl
?
Cl
Cl Cl Cl Cl
Cl
Cl Cl Cl Cl Cl
I II III IV V
A) I and II
B) II and III
C) I and IV
D) V
E) All of the above are equally likely to be formed
Ans: A
208
Section: 8.2
14. Consider the addition of HCl to 3-methyl-1-butene. The major product of the reaction
would be:
A) 1-Chloro-2-methylbutane
B) 1-Chloro-3-methylbutane
C) 2-Chloro-2-methylbutane
D) 2-Chloro-3-methylbutane
E) 1-Chloropentane
Ans: C

Section: 8.2
Difficulty Level: Hard
15. What are possible products for the following reaction?
HBr
A)
Br
B) Br
+ enantiomer
C) Br
D) A) and C)
E) None of the above
Ans: D
209
Topic: Reaction Sequences
Section: 6.5, 8.2
16. What is the major product of the following reaction sequence?

1. HBr
2. NaCN, DMSO
A)
CN
B)
CN + enantiomer
Cl
C)
CN + enantiomer
CN
D)

Ans: E
210
Section: 7.6C, 8.2

1. HI
2. t-BuOK, t-BuOH
A)
B)
C)
D)

Ans: B
211
Section: 7.6C, 8.2

1. HCl
2. t-BuOK, t-BuOH
A)
B)
C)
D)
E)
O
Ans: C
212
Section: 7.6C, 8.2

Cl 1. t-BuOK, t-BuOH
2. HBr
A) Br
B) Br
Br
C)
Br
D) Br

Ans: C

Section: 8.2B
20. In general, when the addition of an unsymmetrical electrophilic reagent to an

unsymmetrical alkene forms the product predicted by Markovnikov's rule, that occurs
because:
A) the product is statistically favored.
B) steric hindrance favors its formation.
C) it is formed via the more/most stable carbocation.
D) it is the more/most stable product.
E) All of the above are reasons.
Ans: C
213
Section: 8.2B
21. What is the chief product of the reaction of IBr with 2-methyl-2-pentene?
A) 2-bromo-3-iodo-2-methylpentane
B) 3-bromo-2-iodo-2-methylpentane
C) 1-bromo-2-iodo-2-methylpentane
D) 2-bromo-1-iodo-2-methylpentane
E) All of the above
Ans: A

Section: 8.5
22. Treating 1-methylcyclohexene with H3O+ would yield primarily which of these?
HO HO
HO
I II III
HO
OH
IV V
A) I and V
B) II
C) III and V
D) IV
E) I, III and V
Ans: D
214
Section: 8.5
23. Which product would you expect from the following reaction?
H3O+
H2O
OH
OH
OH
I II III
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D

Section: 8.5
24. What is the chief product of the acid-catalyzed hydration of 2,5-dimethyl-2-hexene?

A) 2,5-dimethyl-1-hexanol
B) 2,5-dimethyl-2-hexanol
C) 2,5-dimethyl-3-hexanol
D) 2,5-dimethyl-2,3-hexanediol
E) 2,5-dimethyl-3,4-hexanediol
Ans: B
215
Section: 8.5
25. Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?

A) (CH3)2C(OH)CH2CH3
B) CH2OHCH(CH3)CH2CH3
C) (CH3)2CHCHOHCH3
D) (CH3)2CHCH2CH2OH
E) CH3CH2CH(CH3)CH2OH
Ans: A

Section: 8.5
26. When either cis- or trans-2-butene is treated with hydrogen chloride in ethanol, the
product mixture that results includes:
A) CH3CH2CH2CH2Cl
B) CH3CH2CH2CH2OCH2CH3
C) CH3CH2CH(CH3)OCH2CH3
D) (CH3)3CCl
E) (CH3)2CHCH2OCH2CH3
Ans: C

Section: 8.5
27. Which alkene would you expect to be most reactive toward acid-catalyzed hydration?
A) 1 pentene
B) trans-2-pentene
C) cis-2-pentene
D) 2-methyl-1butene
E) All of these would be equally reactive.
Ans: D
216
Section: 8.6
a. Hg(OAc)2, H2O
b. NaBH4, NaOH
A)
B) OH
+ enantiomer
C)
OH
D) HO

Ans: B
217
Section: 8.6
a. Hg(OAc)2, H2O
b. NaBH4, NaOH
A) O
H
O
B)
+ enantiomer
OH
C) OH
D)
+ enantiomer
OH
Ans: C
218
Section: 8.6
a. Hg(OAc)2, H2O
b. NaBH4, NaOH
A) OH
+ enantiomer
B) OH
+ enantiomer
OH
C) OH
+ enantiomer
D)
+ enantiomer
HO
E) OH
+ enantiomer
Ans: D
219
Section: 8.6
a. Hg(O2CCF3)2, CH3OH
b. NaBH4, NaOH
A)
+ enantiomer
O
B)
+ enantiomer
O
C) OH
D) O

Ans: D
220
Section: 8.6
a. Hg(O2CCF3)2, EtOH
b. NaBH4, NaOH
A)
O
B)
O
C) O
D)
HO
+ CO2
O
E)
HO
Ans: B
221
Section: 6.16, 8.6

Br
1. NaOEt, HOEt, heat
2a. Hg(O2CCF3)2, CH3OH

2b. NaBH4, NaOH
A)
OCH3
B)
OH
C) OCH3
D) OH

Ans: A
222
Section: 7.15A, 8.6

1. H2, Pd/CaCO3, quinoline
2a. Hg(OAc)2, H2O

2b. NaBH4, NaOH
A)
OH
B)
OH
C)
O
D) HO
E) HO
Ans: B
223
Section: 6.16, 8.7, 8.8, 8.9

1. EtOH, EtONa, heat
Cl 2a. BH3:THF
2b. H2O2, NaOH
A)
HO
B)
+ enantiomer
OH
C)
+ enantiomer
OH
D)
E) An equal mixture of B) and C)

Ans: C
224
Section: 7.15A, 8.7, 8.8, 8.9

1. H2, Pd/CaCO3, quinoline
2a. BH3:THF
2b. H2O2, NaOH
A)
OH
B)
H
O
C)
HO
D)
E)
OH
Ans: E
225
Section: 6.16, 8.8, 8.9, 8.10

Br 1. EtOH, EtONa, 60 oC
2a. O3, CH2Cl2, -78 oC

2b. Me2S
A) O
O
B) CHO
CHO
C) OH OH
+ enantiomer
D) O
CHO

Ans: D
226
Section: 6.17, 8.8, 8.9, 8.10

Br
1. EtOH, 70 oC
2a. O3, CH2Cl2, -78 oC

2b. Me2S
A) O
O
B) OH
OH
C) O
O
D) CHO
CHO
Ans: A
227
Section: 8.7, 8.8, 8.9
a. BH3:THF
b. H2O2, NaOH
A) OH
+ enantiomer
B)
C)
OH
D) H
+ HCHO
O
E)
OH
Ans: E
228
Section: 8.7, 8.8, 8.9
a. BH3:THF
b. H2O2, NaOH
A) HO
B) O
+ CO2
OH
C)
D) OH
+ enantiomer
E) OH
+ enantiomer
OH
Ans: A
229
Section: 8.7, 8.8, 8.9
a. BH3:THF
b. H2O2, NaOH
A)
HO
B) HO
+ enantiomer
C) HO
+ enantiomer
D) OH
+ enantiomer

Ans: B
230
Section: 8.7, 8.8, 8.9
a. BH3:THF
b. H2O2, NaOH
A)
+ enantiomer
OH
OH
B) O
H
O
C)
+ enantiomer
OH
D)
OH
E)
+ enantiomer
OH
Ans: E
231
Section: 8.7, 8.8, 8.9
a. BH3:THF
b. H2O2, NaOH
A)
+ enantiomer
OH
B)
OH
C) OH
+ enantiomer
D) All the above are major products

E) A mixture of A) and C)
Ans: E
232
Section: 8.7, 8.8, 8.9, 8.11
a. BD3:THF
b. CH3CO2D
A)
+ enantiomer
OH
B)
+ enantiomer
D
C)
+ enantiomer
D D
D)
+ enantiomer
D D
E)
D
Ans: D
233
Section: 8.7, 8.8, 8.9, 8.11
a. BH3:THF
b. CH3CO2D
A)
+ enantiomer
D
B) OH + enantiomer
C) D + enantiomer
D) O2CCH3 + enantiomer
Ans: C

Section: 8.12

Br2, CCl4
?
CH3 CH3 CH3 CH3

H Br Br H H Br Br H
H Br Br H Br H H Br
C3H7 C3H7 C3H7 C3H7
I II III IV
A) Equal amounts of I and II

B) Equal amounts of II and III
C) Equal amounts of III and IV
D) I and II as major products, III and IV as minor products
E) All of the above in equal amounts
Ans: A
234
Section: 8.12

Br2, CCl4
?
C2H5 C2H5 C2H5 C2H5

H3C Br Br CH3 H3C Br Br CH3
H Br Br H Br H H Br
C3H7 C3H7 C3H7 C3H7
I II III IV

Ans: A

Section: 8.12
48. Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the

product would:
A) be a racemic form and, in their most stable conformation, they would have both bromine
atoms equatorial.
B) be a racemic form and, in their most stable conformation, they would have one bromine
atom equatorial and one axial.
C) be a meso compound and, in its most stable conformation, it would have both bromine
atoms equatorial.
D) be a meso compound and, in its most stable conformation, it would have one bromine
atom equatorial and one axial.
E) be a pair of diastereomers and, in their most stable conformation, one would have the
bromines equatorial and axial, and the other would have the bromines equatorial and
equatorial.
Ans: A
235
Section: 2.16, 4.16, 8.12
49. Compound X has the molecular formula C6H10. X decolorizes bromine in carbon
tetrachloride. X also shows IR absorption at about 3300 cm-1. When treated with excess
hydrogen and a nickel catalyst, X yields 2-methylpentane. The most likely structure for
X is:
A)
B)
C)
D)
E)
Ans: D

Section: 7.10, 8.12

1. Br2, CCl4
2a. NaNH2 (excess), NH3

2b. H3O+
A)
B)
C)
D)
Br
Ans: B
236
Topic: Synthetic Strategy
Section: 7.10, 7.15A, 8.12
51. A synthetic strategy for converting trans-2-butene into pure cis-2-butene would consist
of which of the following?
A) Reaction with H2, Ni2B (P-2)
B) Reaction with i) Br2, CCl4; ii) 2 NaNH2, NH3(l); iii) Na, NH3 (l)
C) Reaction with H3O+, heat
D) Reaction with i) Br2, CCl4; ii) 2 NaNH2, NH3(l); iii) H2, Ni2B (P-2)
E) None of these will successfully effect the desired transformation.
Ans: D

Section: 7.15A, 8.12

1. H2, P-2
2. Br2, CCl4
A) Br
+ enantiomer
Br
B) Br
+ enantiomer
Br
C) Br
+ enantiomer
D)
+ enantiomer
Br
E) Br Br
Br Br
Ans: B
237

1. H2, Lindlars catalyst
2. Br2, CCl4
A) Br
+ enantiomer
Br
B) Br
+ enantiomer
Br
C) Br
+ enantiomer
D)
+ enantiomer
Br
E) Br Br
Br Br
Ans: B

Section: 7.10, 7.15B, 8.12
54. Which reaction sequence would convert cis-2-butene to trans-2-butene?

A) Br2/CCl4; then 2 NaNH2; then H2/Ni2B(P-2)
B) Br2/CCl4; then 2 NaNH2; then Li/liq. NH3
C) H3O+, heat; then cold dilute KMnO4
D) HBr; then NaNH2; then H2, Pt
E) None of these
Ans: B
238
Section: 8.2, 8.12
55. The reaction of BrCl (bromine monochloride) with 1-methylcyclopentene will produce
as the predominant product:
CH3 CH3 CH3 CH3 CH2Cl

Br Br Cl Br
Cl
Cl Br Cl Br
+ + + + +
enantiomer enantiomer enantiomer enantiomer enantiomer
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Structure Elucidation

Section: 8.4, 8.12
56. Which of these compounds will react with cold concd. H2SO4, as well as Br2 in CCl4 ?
A) CH3CH2CH=CHCH3
B) CH3CH2CH2CH=CH2
C) CH3CH2CCCH3
D) (CH3)2CHCCH
E) All of these
Ans: E
239
Section: 8.13
57. Which reaction is NOT stereospecific?
Br2/CCl4 Br2/H2O
trans-2-Butene cis-2-Pentene
I II
D2/Pd
1-Methylcyclohexene
III
dil KMnO4 HBr

2-Methyl-2-heptene trans-2-Hexene
5oC
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E
240
Section: 8.12, 8.13
Br2, CCl4
A)
Br
B)
Br + enantiomer
Br
C)
+ enantiomer
Br
Br
D)
Br
Ans: B
241
Section: 8.12, 8.13
Cl2, CCl4
A) Cl
B)
Cl
+ enantiomer
Cl
C)
Cl
+ enantiomer
Cl
D)
Cl
+ enantiomer

Ans: C
242
Section: 8.12, 8.13
60. Reaction of trans-2-hexene with a solution of Br2 in CCl4 produces:

H Br H
Br H Br
Br H H
H Br Br
I II III
Br
H
Br H H
H Br Br
IV V
A) I and II
B) II and V
C) III and IV
D) IV and V
E) V
Ans: C

Section: 8.12, 8.13
61. The reaction of Br2/CCl4 to cyclohexene would produce the compound(s) represented by
structure(s):
H H H
H Br Br
Br Br Br
Br H H
I II III
A) I alone
B) II alone
C) II and III
D) III alone
E) I , II and II
Ans: C
243
Section: 8.14
62. Which of these is not a possible product when cyclopentene reacts with an aqueous
solution of bromine?
Br OH Br Br OH
OH Br Br Br OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E

Section: 8.14

Br2, H2O
?
Br Br OH Br OH
OH Br Br Br OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A
244
Section: 8.14
Cl2, H2O
A) Cl
OH
B) OH
+ enantiomer
Cl
C) Cl
OH
D) OH
Cl

Ans: C

Section: 8.14
65. Which of these compounds belongs to the class of substances commonly known as
"halohydrins"?
A) BrCH2CH2Cl
B) ClCH2CO2H
C) ICH2CH2OH
D) FCH2CH2NH2
E) HOCH2COCl
Ans: C
245
Section: 8.14
Br2, H2O
A)
+ enantiomer
HO
Br
B)
+ enantiomer
HO
OH
C)
+ enantiomer
Br
OH
D)
+ enantiomer
HO
Br
E)
+ enantiomer
Br
OH
Ans: A
246
Section: 8.14
Br2, CH3OH
A)
OH
+ enantiomer
Br
B) OCH3
+ enantiomer
Br
C)
Br
+ enantiomer
H3CO
D)
OCH3
+ enantiomer
Br
Ans: D
247
Section: 6.5, 8.14

1. Br2, H2O
2. NaH, THF
A)
Br + enantiomer
OH
B)
O- Na+ + enantiomer
Br
C)
OH + enantiomer
Br
D)
O + enantiomer

Ans: D

Section: 8.12, 8.14
69. Which of these compounds is not formed when gaseous ethene is bubbled into an
aqueous solution of bromine, sodium chloride and sodium nitrate?
A) BrCH2CH2Br
B) BrCH2CH2Cl
C) BrCH2CH2OH
D) ClCH2CH2OH
E) BrCH2CH2ONO2
Ans: D
248
Section: 8.15B
CHCl3
t-BuOK
A) Cl
Cl
+ enantiomer
B)
C)
Cl + enantiomer
Cl
D) Cl
Cl + enantiomer

Ans: A
249
Section: 7.15B, 8.15B

1. Li, CH3CH2NH2
2. t-BuOK, CHCl3
A) Cl Cl
+ enantiomer
B)
Cl
+ enantiomer
Cl
C)
Cl
+ enantiomer
Cl
D) Cl Cl
+ enantiomer

Ans: D
250
Section: 8.15C
I2CH2
Zn(Cu)
A) I I
B)
C) I
D)

Ans: D
251
Section: 8.16
73. What product would result from the following reaction?
KMnO4, H2O
?
cold, dilute
CO2H
O
K MnO4 OH OH
I II III
OH OH OH OH
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Section: 8.16
74. Which reagent(s) given below could be used to synthesize cis-1,2-cycloheptanediol

from cycloheptene?
A) KMnO4, OH, 5oC
B) KMnO4, H3O+, 75oC
C) H2SO4, heat
D) All of these
E) None of these
Ans: A
252
Section: 8.16
75. Cyclohexene is treated with cold dilute alkaline KMnO4. Assuming syn addition, the
spatial arrangement of the two hydroxyl groups in the product would be:
A) equatorial-axial
B) axial-axial
C) equatorial-equatorial
D) coplanar
E) trans
Ans: A

Section: 8.16
76. Hydroxylation of cis-2-pentene with cold alkaline KMnO4 yields
CH3 CH3 CH3 CH3

H OH HO H H OH HO H
H OH HO H HO H H OH
C2H5 C2H5 C2H5 C2H5
I II III IV
Ans: A
253
Section: 8.16
77. 3,3-dimethylcyclohexene is subjected to reaction with cold, dilute KMnO4, to give 3,3-
dimethyl-1,2-cyclohexanediol. In the most stable conformation of the product, the
hydroxyl groups would be:
A) both axial
B) both equatorial
C) axial-equatorial
D) coplanar
E) None of these
Ans: C

Section: 2.16, 4.16, 8.16
78. An optically active compound, Y, with the molecular formula C7H12 gives a positive test
with cold dilute KMnO4 and shows IR absorption at about 3300 cm-1. On catalytic
hydrogenation, Y yields Z(C7H16) and Z is also optically active. Which is a possible
structure for Y?
A) CH3CH2CH2CH2CH2CCH
B) (CH3)2CHCH2CH2CCH
C) CH3CH2CH(CH3)CH2CCH
D) CH3CH2CH(CH3)CCCH3
E) CH2=CHCH(CH3)CH2CH=CH2
Ans: C
254
Section: 2.16, 4.16, 7.13, 8.16
79. An optically active compound, A, with the molecular formula C7H12 reacts with cold
dilute KMnO4 and gives IR absorption at about 3300 cm-1. On catalytic hydrogenation,
A is converted to B (C7H16) and B is also optically active. Which is a possible structure
for A?
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E

80. Which alkene would react with cold dilute alkaline permanganate solution to form an
optically inactive and irresolvable product?
A)
B)
C)
D)
E)
Ans: C
255
Section: 6.16, 8.16

Cl
2. KMnO4, NaOH, cold
A) O
+
O OH
B)
OH + CO2
O
C)
+ enantiomer
OH
OH
D)
+ enantiomer
OH OH
Ans: C
256
82. What is the final product of the following synthesis?
H2 i. OsO4
2-Butyne C4H8 Final Product
Ni2B (P-2) ii. NaHSO4
CH3 CH3 CH3 CH3

HO OH HO H HO H H OH
H H HO H H OH HO H
CH3 CH3 CH3 CH3
I II III IV
A) I
B) II
C) III
D) IV
E) An equimolar mixture of III and IV
Ans: B

Section: 8.4, 8.12, 8.16
83. Which of the following reagents might serve as the basis for a simple chemical test that
would distinguish between pure 1-pentene and pure pentane?
A) Bromine in carbon tetrachloride
B) Dilute aqueous potassium permanganate
C) Concentrated sulfuric acid
D) All of the above
E) Answers A) and B) only
Ans: D
257
Section: 8.4, 8.12, 8.16
84. Which reagent or test could be used to distinguish between 2-methyl-2-pentene and 2-
methylpentane?
A) Br2/CCl4
B) KMnO4, OH
C) Concd. H2SO4
D) Two of the above
E) All of the above
Ans: E

Section: 5.12A, 4.16, 8.12, 8.16
85. Which reaction would yield a meso compound?

A) Br2/CCl4
cis-2-Butene
B) H2/Pd
cis-2-Butene
C) cis-2-Butene i) OsO4
ii) NaHSO3
D) dil KMnO4
trans-2-Butene
5oC
E) None of these
Ans: C

Section: 5.14A, 8.5, 8.12, 8.16
86. Which reaction would give a meso compound as the product?

A) Cyclopentene + Br2/CCl4
B) Cyclopentene + OsO4, then NaHSO3
C) Cyclopentene + H3O+
D) Cyclopentene + Cl2, H2O
E) More than one of these
Ans: B
258
Section: 8.2, 8.12, 8.13, 8.16
87. A pair of enantiomers results from which of these reactions?

A) cyclopentene + cold, dil. KMnO4
B) trans-2-butene + Br2
C) 1-pentene + HCl
D) cis-2-butene + D2/Pt
E) cyclobutene + OsO4, then Na2SO3
Ans: C

Section: 8.2, 8.12, 8.13, 8.16
88. Which of the following reactions would yield the final product as a racemic form?
A) Cyclohexene + Br2, CCl4
B) Cyclohexene + cold, dilute KMnO4 and OH-
C) Cyclohexene + HCl
D) Cyclohexene + OsO4, then NaHSO3
E) Cyclohexene + D2/Pt
Ans: A
259
Section: 8.2, 8.12, 8.13, 8.16
89. Which reaction is regioselective?

Cl
ICl I
I
Br2 Br
II
Br
OH
III KMnO4
OH
H
D2/Ni D
IV
D
H
A) I
B) II
C) III
D) IV
E) None of these
Ans: A

Section: 8.2, 8.4, 8.12, 8.13, 8.14, 8.16
90. Which reaction would yield a racemic product?

A) Cyclopentene + D2/Pt
B) Cyclopentene + OsO4, then Na2SO3
C) Cyclopentene + Br2/H2O
D) Cyclopentene + cold, dilute KMnO4
E) Cyclopentene + dilute H2SO4
Ans: C
260
Section: 8.6, 8.7, 8.8, 8.9, 8.12, 8.13, 8.16
91. Which reaction of an alkene proceeds with anti addition?

A) Hydroboration/oxidation
B) Bromination
C) Oxidation with cold KMnO4
D) Hydrogenation
E) Oxymercuration-demercuration
Ans: B

Section: 8.16A
a. OsO4, pyridine
b. H2O, NaHSO3
A) OH
+ enantiomer
OH
B) OH
+ enantiomer
OH
C) O
H
+
H
O
D) CH3CO2H + (CH 3)2CHCO 2H

Ans: A
261
Section: 6.16, 8.16A

Br
1. EtOH, EtONa
2a. OsO4, pyridine

2b. H2O, NaHSO3
A) OH
HO
B) OH
HO
C) Br
+ enantiomer
HO
D) O O
+
H
Ans: C
262
Section: 8.17A
94. The most resistant compound to the action of hot alkaline KMnO4 is:
A) Pentane
B) 1-Pentene
C) 2-Pentene
D) 2-Pentyne
E) Cyclopentene
Ans: A

Section: 8.17A
a. KMnO4, NaOH, heat
b. H3O+
A) O
OH
HO + enantiomer
O
B) HO
HO + enantiomer
C) O
OH
HO
O
D) O
H
O
E) O
OH
O
Ans: E
263
Section: 8.17A
96. Which alkene would yield only CH3CH2COOH on oxidation with hot alkaline
potassium permanganate (followed by acid work-up)?
A) (E)-2-hexene
B) (Z)-2-hexene
C) 2-methyl-2-pentene
D) (E)-3-hexene
E) (E)-4-methyl-2-pentene
Ans: D

97. Determine a possible structure for an alkene, X, formula C9H14, on the basis of the
following information: X adds one mole of hydrogen on catalytic hydrogenation. On
treatment with hot basic KMnO4 followed by acidification, X yields the following
dicarboxylic acid.
HO O
O OH
A possible structure for X might be:
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
264
Section: 8.5, 8.12, 8.13, 8.17A
98. Which of the following reactions of cyclobutene would yield a meso product?
A) Reaction with H3O+, H2O
B) Reaction with Br2, CCl4
C) Reaction with Cl2, CCl4
D) Reaction with D2, Pt
E) Reaction with hot, alkaline KMnO4, followed by acid workup
Ans: D

Section: 8.17B
a. O3, CH2Cl2, -78 oC
b. Me2S
A)
OH
+ enantiomer
OH
B) O
HO
O
C) O
H
O
D) O
H
H
O
Ans: C
265
Section: 8.17B
a. O3, CH2Cl2, -78 oC
b. Me2S
A)
CO2H + CO2
B)
SMe2
C) OH
+ enantiomer
OH
D)
CHO + HCHO

Ans: D

Section: 8.17B
101. Which substance would undergo the following reaction?
i. O3 H
? ii. Zn, HOAc +
O H O
A) 4-Hexen-1-yne
r
B) 3-methyl-1-hexene
C) (E)-2-hexene
D) (Z)-2-hexene
E) 4-methyl-1-pentene
Ans: E
266
Section: 8.17B
a. O3, CH2Cl2, -78 oC
b. Me2S
A)
HO
B)
O
(Racemic)
C)
O
+ CO2
D)
O
+ HCHO

Ans: D
267
Section: 8.17B
103. Ozonolysis of compound Z yields the products shown below. What is the structure of Z?
O O O
1) O3
Z 2HCH + CH3CCH2CH
2) Zn, HOAc
I II III
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B
268
Section: 8.17B
104. An alkene with the molecular formula C10H18 is treated with ozone and then with zinc
and acetic acid. The only product isolated from these reactions is:
O
O
What is the structure of the alkene?
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Section: 8.17B
105. Consider the ozonolysis products obtained from all the unbranched and unsymmetrical
isomers of heptene. The reaction product in each case would consist of:
A) a single aldehyde.
B) an aldehyde and a ketone.
C) two different ketones.
D) two different aldehydes.
E) a single ketone.
Ans: D
269
Section: 4.16, 8.17B
106. An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane.

Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single
organic product. The structure of the alkene is:
A) CH3
CH3CH=C-CHCH2CH3 (cis or trans)
CH3
B) CH3
CH3CH2C=CCH3 (cis or trans)
CH2CH3
C) CH3
CH2=CCH2CHCH2CH3
CH3
D) CH2
CH3CH2CCHCH2CH3
CH3
E) CH3
CH3CH2CHCHCH=CH2
CH3
Ans: B
270
107. Compound C has the molecular formula C7H12. On catalytic hydrogenation, 1 mol of C
absorbs 1 mol of hydrogen and yields a compound with the molecular formula C7H14.
On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only:
O
O
The structure of C is:
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E

108. An alkene with the molecular formula C8H16 undergoes ozonolysis to yield a mixture of
(CH3)2C=O and (CH3)3CCHO. The alkene is:
A) 2,2-Dimethyl-2-hexene
B) 2,3-Dimethyl-2-hexene
C) 2,4-Dimethyl-2-hexene
D) 2,4,4-Trimethyl-2-pentene
E) More than one of the above is a possible answer.
Ans: D
271

Br
2a. KMnO4, NaOH, heat
2b. H3O+
A)
OH
+ enantiomer
OH
B) O
H
H
O
C) O
O
D) O
OH
HO
O
E)
+ CO2
O
Ans: C
272
Section: 7.6C, 8.17B

1. t-BuOK, t-BuOH
Cl
2a. O3, CH2Cl2, -78 oC

2b. Me2S
A) O
+ HCHO
B) O
H
O
C) OH
OH
D)
OH + enantiomer
OH
Ans: A

Section: 2.16, 4.16, 7.13, 8.17B
111. One mole of an optically active compound, X, with the molecular formula C6H8 reacts
with three moles of hydrogen in the presence of a catalyst to yield an optically inactive
product that cannot be resolved. X also exhibits IR absorption at approximately 3300
cm-1. Which is a possible structure for X?
A) (E)-4-hexen-1-yne
B) (Z)-4-hexen-1-yne
C) (E)-2-hexen-4-yne
D) 2-methyl-1-penten-3-yne
E) 3-methyl-1-penten-4-yne
Ans: E
273
Section: 7.15B, 8.17B

1. Li, CH3CH2NH2, -78 oC
2a. O3, CH2Cl2, -78 oC

2b. Me2S
A)
OH
+ enantiomer
OH
B)
+ HCHO
CHO
C)
+ CO2
CO2H
D)
OH
Ans: A
274
Section: 8.18
113. Select the structure of the major product formed in the following reaction.
2 Cl2
?
Cl Cl Cl
Cl Cl
Cl Cl
I II III
Cl Cl Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
275
Section: 8.19
114. Select the structure of the major product formed in the following reaction.
2 HCl
?
Cl
Cl Cl
Cl
I II III
Cl Cl Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D

Section: 8.19
115. Addition of 2 mol of HCl to 1-butyne would yield:

A) CH3CH2CH2CHCl2
B) CH3CH2CCl2CH3
C) CH3CH2CHClCH2Cl
D) CH3CH2CH=CHCl
E) CH3CHClCHClCH3
Ans: B
276
Section: 8.19
116. Addition of excess HCl to 2-methyl-3-heptyne would produce:
2-methyl-3,3-dichloroheptane 2-methyl-2,3-dichloroheptane
I II
2-methyl-4,4-dichloroheptane 2-methyl-3,4-dichloroheptane
III IV
2-methyl-3-chloroheptene
A) I and II
B) I and III
C) II and IV
D) V
E) All of the above
Ans: B

Section: 7.10, 8.19
117. The conversion of ethylene to vinyl bromide can be accomplished by use of these
reagents in the order indicated.
A) (1) HBr; (2) NaOC2H5
B) (1) Br2; (2) NaOC2H5
C) (1) Br2; (2) H2O
D) (1) NaNH2; (2) HBr
E) (1) HBr; (2) H2SO4
Ans: B
277
Section: 8.2, 8.19

1. HBr (1 equiv)
2. HCl (1 equiv)
A) Cl
Br
B) Br
Cl
C) Cl Br
D) Cl
Br
Ans: C
278
Section: 8.20
a. KMnO4, NaOH, heat
b. H3O+
A)
OH
OH
B) CHO
+ HCHO
C) CO2H
+ CO2
D) CO2H

Ans: C

Section: 8.20
120. An unknown compound, A, has the molecular formula C7H12. On oxidation with hot
aqueous potassium permanganate, A yields CH3CH2COOH and (CH3)2CHCOOH.
Which of the following structures best represents A?
A)
B)
C)
D)
E)
Ans: C
279
Section: 8.17B, 8.20
121. What compound would yield an equimolar mixture of CH3CH2CH2CHO and CH3CHO
upon treatment with O3, followed by Zn/HOAc?
A) 1-Hexene
B) cis-2-Hexene
C) trans-2-Hexene
D) More than one of these
E) None of these
Ans: D

Section: 2.16, 8.18, 8.20
122. Which of the following could be used as the basis for a simple test that would
distinguish between 1-pentyne and pentane?
A) IR examination
B) Br2/CCl4
C) KMnO4/H2O
D) Two of these
E) All of these
Ans: E

Section: 2.16, 8.4, 8.18, 8.20
123. Which reagent or test could be used to distinguish between 3-pentyne and 1-pentyne?
A) Br2/CCl4
B) IR examination
C) Concd. H2SO4
D) KMnO4,OH-
E) None of these
Ans: B
280
Section: 2.16, 8.4, 8.12, 8.16, 8.18, 8.20
124. A reagent or test that could be used to distinguish between 1-pentene and 1-pentyne
would be:
A) Bromine in carbon tetrachloride
B) Dilute aqueous potassium permanganate
C) Chlorine in carbon tetrachloride
D) H2SO4
E) IR examination
Ans: E

Section: 2.16, 8.18, 8.19, 8.20
125. Which of the following could be used to distinguish between 1-octyne and 3-octyne?
A) Treatment with 2 mol of HX
B) Addition of water
C) Reaction with KMnO4
D) Decolorization of bromine in CCl4
E) IR examination
Ans: E

Section: 7.13, 8.18, 8.19, 8.20
126. 2-Pentyne will not react with:

A) H2, Pt
B) Br2
C) NH3
D) H2SO4
E) KMnO4/H2O
Ans: C
281
SHORT ANSWER QUESTIONS

Section: 8.1
127. bonds are quite susceptible to reaction with electron-seeking reagents, also referred to as
____________________.
Ans: electrophiles

Section: 8.2
128. The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is
called ____________________.
Ans: Markovnikov's Rule

Section: 8.2
129. Provide a mechanistic explanation for the following observation: The same major product is
obtained when 2-ethyl-1-hexene and 3-methyl-2-heptene are allowed to react with HCl.
Ans: HCl
Cl
HCl
most stable
carbocation
Both alkenes are unsymmetrically substituted: the major product is a consequence of

regioselective addition to the double bond. Upon reaction with HCl, electrophilic
addition of a proton results in the formation of the most stable intermediate carbocation,
which then reacts with Cl, to give the observed product.
282
Section: 8.2
130. Give a mechanistic explanation for the formation of the following product in significant yield.
What other product(s) might also be obtained? Explain clearly.
HI I
Ans:
H+ + fast I I
+
+ I
I
The regioselective addition of a proton first generates a secondary carbocation, which

can undergo rearrangement to a more stable 3o carbocation by two alternate pathways.
One pathway results in ring expansion to a more stable 5-membered ring. This pathway
is thus more likely, which would then lead to the observed product. The other pathway
is less likely, since ring strain is not relieved; however, this could lead to a minor
product, as shown above.

Section: 8.2C
131. When a reaction that could potentially yield two or more constitutional isomers instead
produces only one as the major product, the reaction is said to be
_____________________.
Ans: regioselective

Section: 8.7, 8.8, 8.9
132. Hydroboration-oxidation is a reaction with _________ stereochemistry and

________________ regiochemistry.
Ans: syn, anti-Markovnikov
283
Topic: Reaction Sequence
Section: 6.16, 8.7, 8.8, 8.9
133. Predict the final product(s) obtained when (2R,3R)-2-bromo-3-methylpentane is subjected to

the following sequence of reactions, briefly explaining your rationale. Provide regiochemical
and stereochemical details as relevant.
i) NaOC2H5/C2H5OH, heat
ii) BH3, THF
iii) H2O2, OH
Ans: Br H H
NaOC2H5 E-3-methyl-2-hexene
H3C H C2H5OH CH3
Hydroboration/oxidation:
(E2: anti
(2R,3R) overall
elimination)
Anti-Markovnikov,
syn addition of H2O
H OH HO H
+
H3C H H CH3
(2S,3R) (2R,3S)
3-methyl-2-pentanol
Heating with sodium ethoxide results in E2 elimination; the anti- elimination leads to
the formation of E-3-methyl-2-hexene as the major product. Subsequent hydroboration
oxidation is regioselective (anti-Markovnikov) and stereospecific (syn), resulting in the
formation of racemic (2S,3R & 2R,3S) 3-methyl-2-pentanol. The other diastereomer
pair (2S,3S & 2R,3R) is not expected to be obtained.

Section: 8.3, 8.6C, 8.8A, 8.12A
134. Even when one or more stereogenic centers are produced as the result of an addition
reaction to an alkene, the product is always formed as a racemic mixture. Why is that?
Ans: Because alkenes are planar, and the reagent can add from either face.
284
Section: 8.13
135. When a particular stereoisomer reacts in such a way that it gives a particular
stereoisomer as a product, even if more than one stereoisomer is theoretically possible,
the reaction is said to be _____________.
Ans: stereospecific

Section: 8.13
136. A reaction in which the reactant is not necessarily chiral but still produces primarily one
stereoisomeric form of the product (or a specific subset of the possible stereoisomers) is
referred to as a _________________ reaction.
Ans: stereoselective

Section: 8.14
137. Draw Fischer projection formulas of the major product of the reaction between E-2-methyl-3-
hexene and aqueous Br2.
Ans: CH(CH ) CH(CH ) CH(CH ) CH(CH )
3 2 3 2 3 2 3 2
Br2 HO H H OH H Br Br H
H Br
+ Br H + HO H
+ H OH
H2O
C2H5 C2H5 C2H5 C2H5
The reaction takes place with anti stereospecificity. Since the alkene is symmetrically
substituted, Markovnikov rule is not applicable, and the reaction is not regioselective.
The product mixture would therefore consist of 2 pairs of enantiomers, that are
constitutional isomers of each other.
285
Section: 8.2, 8.14
138. Predict the major product(s) of the following reaction, giving regiochemical and/or
stereochemical details as relevant.
Br2, H2O
?
Ans:
OH + OH
Br Br
H H
The reaction takes place with Markovnikov regioselectivity and anti stereospecificity,
giving a racemic mixture of the halohydrin as the major product.

Section: 8.15
139. Carbenes are frequently produced by -elimination reactions. These are reactions in
which the proton being lost and the leaving group are ___________.
Ans: both attached to the same carbon

Section: 8.15
140. Neutral divalent carbon compounds are called ___________.

Ans: carbenes

Section: 8.15C
141. Predict the structure of product obtained when cis-2-hexene is allowed to react with Zn/CH2I2.
Ans: H H
Zn, CH2I2
H + H
The Zn/CH2I2 produces a carbene which reacts with the alkene to give the corresponding
cyclopropane derivative. The reaction proceeds with retention of alkene
stereochemistry, resulting in a racemic mixture of the two cis enantiomers.
286
Section: 8.16
142. Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-2-methyl-
3-hexene and cold, alkaline KMnO4.
Ans: CH(CH ) CH(CH )
3 2 3 2
cold, dil H OH HO H
H OH + HO H
KMnO4
C2H5 C2H5
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol
product.

Section: 8.16
143. Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-3-methyl-
3-hexene and cold, alkaline KMnO4.
Ans: CH2CH3 CH2CH3
cold, dil H3C OH HO CH3
H OH + HO H
KMnO4
C2H5 C2H5
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol
product.

Section: 8.17A
144. Predict the product(s) of the oxidation of 2,3,4-trimethyl-1,5-heptadiene with hot, alkaline
KMnO4.
Ans: OH
hot, alkaline CO + H O + O +
2 2 O
KMnO4 O
OH
287
Section: 4.16, 8.12, 8.17B
145. Deduce the structure of an unknown compound A, C8H14, from the following data. Briefly, but
clearly explain your rationale. A decolorizes Br2/CCl4, and upon reaction with excess H2/Ni,
affords 1-ethyl-2-methylcyclopentane. When A is subjected to ozonolysis, the following
product is obtained.
O O
Ans: A must be 3-ethyl-4-methylcyclopentene. This given data can be explained as shown

below:
C8H14: Index of Hydrogen Deficiency of A = 2
decolorizes Br2,CCl4: A must contain pi bonds
A H2, Ni
A must contain some the same carbon

ozonolysis skeleton and one pi bond
O
O O
O
pi bond position in A deduced from the

structure of the ozonolysis product

Section: 8.12, 8.18
146. The decolorization of molecular bromine is often used as a functional group test to
detect the presence of ________________.
Ans: carbon-carbon multiple bonds; or, alkenes and alkynes
288

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Chapter Eight

MULTIPLE CHOICE QUESTIONS

Topic: General Information

Topic: Reaction Products

3. Markovnikov addition of HI to 2-methyl-2-butene involves:

Topic: Reaction Products

4. What is the major product for the following reaction?

5. What would be the major product of the following reaction?

6. Treating 1-methylcyclohexene with HCl would yield primarily which of these?

Topic: Reaction Products

Topic: Reaction Products

9. What is the major product for the following reaction?

10. What is the major product for the following reaction?

11. What is the major product for the following reaction?

E) More than one of the above

Topic: Reaction Products

13. Addition of hydrogen chloride to the following molecule would produce:

Topic: Reaction Products

15. What are possible products for the following reaction?

16. What is the major product of the following reaction sequence?

E) None of the above

17. What is the major product of the following reaction sequence?

E) More than one of the above

18. What is the major product of the following reaction sequence?

19. What is the major product of the following reaction sequence?

E) None of the above

Topic: Reaction Products

20. In general, when the addition of an unsymmetrical electrophilic reagent to an

Topic: Reaction Products

Topic: Reaction Products

24. What is the chief product of the acid-catalyzed hydration of 2,5-dimethyl-2-hexene?

25. Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?

Topic: Reaction Products

Topic: General Information

28. What is the major product for the following reaction?

E) More than one of the above

29. What is the major product for the following reaction?

30. What is the major product for the following reaction?

31. What is the major product for the following reaction?

E) None of the above

32. What is the major product for the following reaction?

33. What is the major product of the following reaction sequence?

2a. Hg(O2CCF3)2, CH3OH

E) More than one of the above

34. What is the major product of the following reaction sequence?

2a. Hg(OAc)2, H2O

35. What is the major product of the following reaction sequence?

E) An equal mixture of B) and C)

36. What is the major product of the following reaction sequence?

37. What is the major product of the following reaction sequence?

2a. O3, CH2Cl2, -78 oC

E) More than one of the above

38. What is the major product of the following reaction sequence?

2a. O3, CH2Cl2, -78 oC

39. What is the major product for the following reaction?

40. What is the major product for the following reaction?

41. What is the major product for the following reaction?

E) More than one of the above

42. What is the major product for the following reaction?

43. What is the major product for the following reaction?

D) All the above are major products

44. What is the major product for the following reaction?