8 PDF

Package title: Solomons Test Bank
Course Title: Solomons 11e

Chapter Number: 8
Question type: Multiple choice
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.
Answer: C
Topic: General Information

Section: 8.1
Difficulty Level: Medium
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
Answer: B
Topic: Reaction Products

Section: 8.1
Difficulty Level: Easy
3) Markovnikov addition of HI to 2-methyl-2-butene involves:
1
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.
Answer: D

Section: 8.2
4) What is the major product for the following reaction?
HI
A) I
+ enantiomer
B) I
+ enantiomer
C) I
I
+ enantiomer
D)
I
+ enantiomer
E)
Answer: A

Section: 8.2
5) What would be the major product of the following reaction?
2
HCl
Cl Cl
Cl Cl
I II III
Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: B

Section: 8.2
6) Treating 1-methylcyclohexene with HCl would yield primarily which of these?

H 3C H3 C H3 C
Cl
Cl Cl
I II III
H 3C Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: C
3
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
Answer: B

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
Answer: B

Section: 8.2
HBr
+ enantiomer
A) Br
4
+ enantiomer
B) Br
Br
+ enantiomer
C)
+ enantiomer
D) Br
E) More than one of these choices.
Answer: C

Section: 8.2
HCl
A) Cl
B) Cl
C) Cl
D) Cl
Cl
E)
Answer: E

Section: 8.2
5
HBr
Br
A)
Br
B)
+ enantiomer
C) Br
Br
D)
Answer: D

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
6
E) V
Answer: 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 these choices are equally likely to be formed.
Answer: A

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
Answer: C

Section: 8.2
7
15) What are possible products for the following reaction?
HBr
Br
A)
Br
+ enantiomer
B)
Br
C)
D) Two of these choices.
E) None of these choices.
Answer: D

Section: 8.2
Difficulty Level: Hard
16) What are the major product(s) formed by treating treating methylcyclopentene with HBr and
MeO-OMe?
A) I
A) II
B) III
C) Two of these choices.
D) None of these choices.
8
Answer: D

Section: 8.2
17) What is the major product of the following reaction sequence?

1. HBr
2. NaCN, DMSO
A) CN
CN + enantiomer
B) Cl
CN + enantiomer
C) CN
D)
Answer: E
Topic: Reaction Sequences

Section: 6.5, 8.2

1. HI
2. t-BuOK, t-BuOH
A)
B)
9
C)
D)
Answer: B

Section: 7.6, 8.2

1. HCl
2. t-BuOK, t-BuOH
A)
B)
C)
D)
E) O
Answer: C

Section: 7.6, 8.2
10
Cl 1. t-BuOK, t-BuOH
2. HBr
Br
A)
Br
Br
B)
C) Br
Br
D)
Answer: C

Section: 7.6, 8.2
21) 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 these choices are reasons.
Answer: C

Section: 8.2
22) 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
11
C) 1-bromo-2-iodo-2-methylpentane
D) 2-bromo-1-iodo-2-methylpentane
E) All of these choices.
Answer: A

Section: 8.2
23) 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
Answer: D

Section: 8.4
24) What is the product(s) formed by treating 3,3 dimethylcyclopentene with H3O+ and heating?
12
A) I only
B) II and IV
C) I and III
D) IV and V
E) none of these choices
Answer: B

Section: 8.4
25) 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
13
E) V
Answer: D

Section: 8.4
26) 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
Answer: B

Section: 8.4
27) 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
Answer: A

Section: 8.4
28) 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
14
E) (CH3)2CHCH2OCH2CH3
Answer: C

Section: 8.4
29) 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-1-butene
E) All of these would be equally reactive.
Answer: D

Section: 8.4
a. Hg(OAc)2, H2O
b. NaBH4, NaOH
A)
OH
+ enantiomer
B)
C) OH
HO
D)
15
Answer: B

Section: 8.5
31) What is the product(s) formed by treating 3,3 dimethyl-1-cyclopentene with Hg(OAc)2 in
THF/water followed by treatment with NaBH4 in NaOH(aq)?
HO HO
HO
+ enantiomer + enantiomer + enantiomer
I II III
OH
HO HO
+ enantiomer meso compound

IV V
A) I only
B) II and IV
C) I and III
D) IV and V
Answer: C

Section: 8.5
a. Hg(OAc)2, H2O
b. NaBH4, NaOH
16
O
A) O
+ enantiomer
B) OH
OH
C)
+ enantiomer
D) OH
Answer: C

Section: 8.5
a. Hg(OAc)2, H2O
b. NaBH4, NaOH
OH
+ enantiomer
A)
OH
+ enantiomer
B) OH
OH
+ enantiomer
C)
17
+ enantiomer
D) HO
OH
+ enantiomer
E)
Answer: D

Section: 8.5
+ enantiomer
A) O
+ enantiomer
B) O
OH
C)
O
D)
Answer: D

Section: 8.5
18
A) O
B)
O
C)
HO
+ CO2
D) O
HO
E)
Answer: B

Section: 8.5
OCH3
A)
OH
B)
19
OCH3
C)
OH
D)
Answer: A

Section: 6.16, 8.5

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

2b. NaBH4, NaOH
A) OH
B) OH
C) O
HO
D)
HO
E)
Answer: B

Section: 7.15, 8.5
20
1. EtOH, EtONa, heat
Cl 2a. BH3:THF
2b. H2O2, NaOH
A) HO
+ enantiomer
B) OH
+ enantiomer
C) OH
D)
E) An equal mixture of two of these choices.
Answer: C

Section: 6.16, 8.6, 8.7, 8.8

1. H 2, Pd/CaCO 3, quinoline
2a. BH 3:THF
2b. H 2O 2, NaOH
OH
A)
B) O
21
C) HO
D)
OH
E)
Answer: E

Section: 7.15, 8.6, 8.7, 8.8

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

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

Section: 6.16, 8.7, 8.8, 8.9
22
41) Which of the following would be produced upon ozonolysis of camphene?
1) O3
2) Me2S
Camphene
CH3
O
O
CO2
II III
I
OH
OH
CH2O
V
IV
A) I, II, V
B) II, III
C) I, V
D) II, V
E) III, IV
Answer: C
Topic: Reaction Product

Section: 8.9

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

2b. Me2S
A) O
23
OH
B) OH
O
C) O
CHO
D) CHO
Answer: A

Section: 6.17, 8.7, 8.8, 8.9
a. BH3:THF
b. H2O2, NaOH
OH
+ enantiomer
A)
B)
C) OH
H
+ HCHO
D) O
24
E) OH
Answer: E

Section: 8.6, 8.7, 8.8
a. BH3:THF
b. H2O2, NaOH
HO
A)
O
+ CO2
B) OH
C)
OH
+ enantiomer
D)
OH
+ enantiomer
E) OH
Answer: A

Section: 8.6, 8.7, 8.8
a. BH3:THF
b. H2O2, NaOH
HO
A)
25
HO
+ enantiomer
B)
HO
+ enantiomer
C)
OH
+ enantiomer
D)
Answer: B

Section: 8.6, 8.7, 8.8
a. BH3:THF
b. H2O2, NaOH
+ enantiomer
OH
A) OH
O
B) O
+ enantiomer
C) OH
D) OH
+ enantiomer
E) OH
26
Answer: E

Section: 8.6, 8.7, 8.8
a. BH3:THF
b. H2O2, NaOH
+ enantiomer
A) OH
B) OH
OH
+ enantiomer
C)
D) All of these choices are major products.
E) A mixture of two of these choices.
Answer: E

Section: 8.6, 8.7, 8.8
a. BD3:THF
b. CH3CO2D
+ enantiomer
A) OH
+ enantiomer
B) D
27
+ enantiomer
D D
C)
+ enantiomer
D D
D)
E) D
Answer: D

Section: 8.6, 8.7, 8.8, 8.10
a. BH3:THF
b. CH3CO2D
+ enantiomer
A) D
OH + enantiomer
B)
D + enantiomer
C)
O2CCH3 + enantiomer
D)
Answer: C

Section: 8.6, 8.7, 8.8, 8.10
50) How many of the products shown below are possible in the following reaction?
28
A) 1
B) 2
C) 4
D) All of them.
E) None of them.
Answer: C

Section: 8.11

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.
29
C) Equal amounts of III and IV.
D) I and II as major products, III and IV as minor products.
E) All of these choices in equal amounts.
Answer: A

Section: 8.11

Br2, CCl4
?
C 2H 5 C 2 H5 C2 H5 C2 H5
H 3C Br Br CH3 H3C Br Br CH3
H Br Br H Br H H Br
C 3H 7 C 3 H7 C3 H7 C3 H7
I II III IV

Answer: A

Section: 8.11
53) 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.
30
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.
Answer: A

Section: 8.11
54) 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)
Answer: D
Topic: Structure Elucidation

Section: 2.16, 4.16, 8.11

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

2b. H3O+
A)
B)
31
C)
D) Br
Answer: B

Section: 7.10, 8.11
56) What reagent sequence might accomplish the following transformation?
A) 1) Br2, 2)excess KOH, 3)H3O+

B) 1) HBr, 2)excess KOH, 3) H3O+
C) 1) HBr, 2)excess NaNH2, 3) H3O+
D) 1) Br2, 2) excess NaNH2, 3) H3O+
Answer: D

Section: 7.10, 8.11
57) 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.
Answer: D
Topic: Synthetic Strategy

Section: 7.10, 7.15, 8.11
32

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

Section: 7.15, 8.11

1. H2, Lindlars catalyst
2. Br2, CCl4
Br
+ enantiomer
A) Br
33
Br
+ enantiomer
B) Br
Br
+ enantiomer
C)
+ enantiomer
D) Br
Br Br
E) Br Br
Answer: B

Section: 7.15, 8.11
60) 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
Answer: B

Section: 7.10, 7.15, 8.11
61) The reaction of BrCl (bromine monochloride) with 1-methylcyclopentene will produce
which of the following as the predominant product:
34
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
Answer: D

Section: 8.2, 8.11
62) 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
Answer: E

Section: 8.4, 8.11
63) Which reaction is NOT stereospecific?
35
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
Answer: E

Section: 8.12
Br2, CCl4
A) Br
Br + enantiomer
B) Br
+ enantiomer
Br
C) Br
36
D) Br
Answer: B

Section: 8.11, 8.12
Cl2, CCl4
Cl
A)
Cl
+ enantiomer
B) Cl
Cl
+ enantiomer
C) Cl
Cl
+ enantiomer
D)
Answer: C

Section: 8.11, 8.12
66) What are the major product(s) formed by treating 1,2-dimethyl cyclopentene with Br2?
37
Bt
Br Br
Br
Br Br
I II III
H
H
Br
Br
IV V
A) I,II
B) II, III
C) IV, V
D) I, III
Answer: D

Section: 8.11, 8.12
67) 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
Answer: C
38
Section: 8.11, 8.12
68) 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
Answer: C

Section: 8.11, 8.12
69) 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
Answer: E

Section: 8.13
39
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
Answer: A

Section: 8.13
Cl2, H2O
Cl
A) OH
OH
+ enantiomer
B) Cl
Cl
C) OH
OH
Cl
D)
Answer: E
40
Section: 8.13
72) Which of these compounds belongs to the class of substances commonly known as
"halohydrins"?
A) BrCH2CH2Cl
B) ClCH2CO2H
C) ICH2CH2OH
D) FCH2CH2NH2
E) HOCH2COCl
Answer: C

Section: 8.13
Br2, H2O
+ enantiomer
HO
A) Br
+ enantiomer
HO
B) OH
+ enantiomer
Br
C) OH
+ enantiomer
HO
D) Br
41
+ enantiomer
Br
E) OH
Answer: A

Section: 8.13
Br2, CH3OH
OH
+ enantiomer
A) Br
OCH3
+ enantiomer
B) Br
Br
+ enantiomer
C) H3CO
OCH3
+ enantiomer
D) Br
Answer: D

Section: 8.13
42
1. Br2, H2O
2. NaH, THF
Br + enantiomer
A) OH
O- Na+ + enantiomer
B) Br
OH + enantiomer
C) Br
O + enantiomer
D)
Answer: D

Section: 6.5, 8.13
76) 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
Answer: D

Section: 8.12, 8.13
43
CHCl3
t-BuOK
Cl
Cl
+ enantiomer
A)
B)
Cl + enantiomer
C) Cl
Cl
Cl + enantiomer
D)
Answer: A

Section: 8.14

1. Li, CH3CH2NH2
2. t-BuOK, CHCl3
Cl Cl
+ enantiomer
A)
Cl
+ enantiomer
B) Cl
Cl
+ enantiomer
C) Cl
44
Cl Cl
+ enantiomer
D)
Answer: A

Section: 7.15, 8.14
I2CH2
Zn(Cu)
I I
A)
B)
I
C)
D)
Answer: D

Section: 8.14
80) What product would result from the following reaction?
45
A) I
B) II
C) III
D) IV
E) V
Answer: C

Section: 8.15
81) 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 choices.
Answer: A

Section: 8.15
82) Which set of reagents might be used to convert bromocyclohexane into cis-1,2-
cyclohexanediol?
A) 1) Potassium tert-butoxide, 2) H3O+

46
B) 1) Potassium tert-butoxide, 2) OsO4, pyridine then NaHSO4(aq)
C) 1) KOH, 2) KMnO4, H+, heating
D) 1) NaOH, 2) H3O+, heating
Answer: B

Section: 8.15
83) 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
Answer: A

Section: 8.15
84) 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

Answer: A

Section: 8.15
47
85) 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
Answer: C

Section: 8.15
86) 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
Answer: C

Section: 2.16, 4.16, 8.15
87) 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?
48
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: E

Section: 2.16, 4.16, 7.13, 8.15
88) Which alkene would react with cold dilute alkaline permanganate solution to form an
optically inactive and irresolvable product?
A)
B)
C)
D)
E)
Answer: C

Section: 5.12, 8.15
49
1. NaOEt, HOEt, heat
Cl
2. KMnO4, NaOH, cold
O
+
A) O OH
OH + CO2
B) O
+ enantiomer
OH
C) OH
+ enantiomer
D) OH OH
Answer: C

Section: 6.16, 8.15
90) 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
50
B) II
C) III
D) IV
E) An equimolar mixture of III and IV.
Answer: B

Section: 7.15, 8.15
91) 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 these choices.
E) Bromine in carbon tetrachloride and dilute aqueous potassium permanganate only
Answer: D

Section: 8.4, 8.11, 8.15
92) 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
Answer: E

Section: 8.4, 8.11, 8.15
93) Which reaction would yield a meso compound?
51
Br2/CCl4
A) cis-2-Butene
H2/Pd
B) cis-2-Butene
i) OsO 4
cis-2-Butene
C) ii) NaHSO3
dil KMnO 4
trans-2-Butene
D) 5 oC
Answer: C

Section: 5.12, 4.16, 8.11, 8.15
94) 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
Answer: B

Section: 5.14, 8.5, 8.11, 8.15
95) 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
Answer: C

Section: 8.2, 8.11, 8.12, 8.15
52
96) Which of the following reactions would yield the final product as a racemic form?
A) Cyclohexene + Br2, H2O

B) Cyclohexene + cold, dilute KMnO4 and OH-
C) Cyclohexene + HCl
D) Cyclohexene + OsO4, then NaHSO3
E) Cyclohexene + D2/Pt
Answer: A

Section: 8.2, 8.11, 8.12, 8.15
97) 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
Answer: A

Section: 8.2, 8.11, 8.12, 8.15
53
98) 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
Answer: C

Section: 8.2, 8.4, 8.11, 8.12, 8.13, 8.15
99) Which reaction of an alkene proceeds with anti addition?
A) Hydroboration/oxidation
B) Bromination
C) Oxidation with cold KMnO4
D) Hydrogenation
E) Oxymercuration-demercuration
Answer: B

Section: 8.5, 8.6, 8.6, 8.8, 8.11, 8.12, 8.15
100) What is the major product of the following reaction?
a. OsO4, pyridine
b. H2O, NaHSO3
OH
+ enantiomer
A) OH
OH
+ enantiomer
B) OH
54
O
H
+
H
O
C)
D) CH3CO2H + (CH3)2CHCO2H
Answer: A

Section: 8.15

Br
1. EtOH, EtONa
2a. OsO 4, pyridine

2b. H2O, NaHSO 3
OH
HO
A)
OH
HO
B)
Br
+ enantiomer
C) HO
O O
+
D) H
Answer: E

Section: 6.16, 8.15
102) The most resistant compound to the action of hot alkaline KMnO4 is:
55
A) Pentane
B) 1-Pentene
C) 2-Pentene
D) 2-Pentyne
E) Cyclopentene
Answer: A

Section: 8.16
a. KMnO4, NaOH, heat
b. H3O+
O
OH
HO + enantiomer
O
A)
HO
HO + enantiomer
B)
O
OH
HO
C) O
O
H
D) O
O
OH
E) O
Answer: E

Section: 8.16
56
104) 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
Answer: D

Section: 8.16
105) 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
Answer: C
57
Section: 4.16, 8.16
106) 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
Answer: D

Section: 8.4, 8.11, 8.12, 8.16
107) What reagents might be used to convert cis-2-butene into trans-2-butene?
A) 1)Br2; 2)NaOEt, EtOH

B) 1)HBr; 2)NaOEt, EtOH
C) 1) H3O+, heat; 2) NaOEt, EtOH
D) 1) H2, Pd/C, 2) NaOEt, EtOH
E) None of these choices
Answer: B

Section: 8.4, 8.11, 8.12, 8.16
a. O3, CH2Cl2, -78 oC
b. Me2S
OH
+ enantiomer
A) OH
58
O
HO
B) O
O
C) O
O
H
H
D) O
Answer: C

Section: 8.16
109) An unknown compound X was subjected to ozonolysis and was found to the following
products. Determine which of the following compounds listed below could be the unknown X?
A) I
B) II
C) III
D) IV
E) V
Answer: E
59
Section: 4.16, 8.16
a. O3, CH2Cl2, -78 oC
b. Me2S
CO2H + CO2
A)
SMe2
B)
OH
+ enantiomer
C) OH
CHO + HCHO
D)
Answer: D

Section: 8.16
111) 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
Answer: E
60
Section: 8.16
a. O3, CH2Cl2, -78 oC
b. Me2S
HO
A)
O
(Racemic)
B)
O
+ CO2
C)
O
+ HCHO
D)
Answer: D

Section: 8.16
113) Ozonolysis of compound Z yields the products shown below. What is the structure of Z?
61
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
Answer: B

Section: 8.16
114) 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
62
D) IV
E) V
Answer: C

Section: 8.16
115) 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.
Answer: D

Section: 8.16
116) 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:
CH3
CH3CH=C-CHCH2CH3 (cis or trans)
A) CH3
CH3
CH3CH2C=CCH3 (cis or trans)
B) CH2CH3
CH3
CH2=CCH2CHCH2CH3
C) CH3
CH2
CH3CH2CCHCH2CH3
D) CH3
63
CH3
CH3CH2CHCHCH=CH2
E) CH3
Answer: B

Section: 4.16, 8.16
117) 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
Answer: E

Section: 4.16, 8.16
118) 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
64
C) 2,4-Dimethyl-2-hexene
D) 2,4,4-Trimethyl-2-pentene
E) More than one of these choices is a possible answer.
Answer: D

Section: 4.16, 8.16

1. NaOEt, HOEt, heat
Br
2a. KMnO 4, NaOH, heat
2b. H 3O+
OH
+ enantiomer
OH
A)
O
H
H
B) O
O
C) O
O
OH
HO
D) O
+ CO2
E) O
Answer: C

Section: 6.16, 8.16
65
1. t-BuOK, t-BuOH
Cl
2a. O3, CH2Cl2, -78 oC

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

Section: 7.6, 8.16
121) 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
Answer: E

Section: 2.16, 4.16, 7.13, 8.16
66
1. Li, CH3CH2NH2, -78 oC
2a. O3, CH2Cl2, -78 oC

2b. Me2S
OH
+ enantiomer
A) OH
+ HCHO
B) CHO
+ CO2
C) CO2H
D) OH
Answer: B

Section: 7.15, 8.16
123) 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
67
A) I
B) II
C) III
D) IV
E) V
Answer: C

Section: 8.17
124) 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
Answer: D

Section: 8.18
125) Addition of 2 mol of HCl to 1-butyne would yield:
A) CH3CH2CH2CHCl2
B) CH3CH2CCl2CH3
C) CH3CH2CHClCH2Cl
68
D) CH3CH2CH=CHCl
E) CH3CHClCHClCH3
Answer: B

Section: 8.18
126) 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
Answer: B

Section: 8.18
127) 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
69
E) (1) HBr; (2) H2SO4
Answer: B

Section: 7.10, 8.18

1. HBr (1 equiv)
2. HCl (1 equiv)
Cl
Br
A)
Br
Cl
B)
Cl Br
C)
Cl
D) Br
Answer: C

Section: 8.2, 8.18
a. KMnO4, NaOH, heat
b. H3O+
70
OH
A) OH
CHO
+ HCHO
B)
CO2H
+ CO2
C)
CO2H
D)
Answer: C

Section: 8.19
130) 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)
Answer: C

Section: 8.19
131) What compound would yield an equimolar mixture of CH3CH2CH2CHO and CH3CHO
upon treatment with O3, followed by Zn/HOAc?
71
A) 1-Hexene
B) cis-2-Hexene
C) trans-2-Hexene
D) More than one of these choices.
Answer: D

Section: 8.16, 8.19
132) 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
Answer: E

Section: 2.16, 8.17, 8.19
133) 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-
Answer: B

Section: 2.16, 8.4, 8.17, 8.19
134) A reagent or test that could be used to distinguish between 1-pentene and 1-pentyne would
72
be:
A) Bromine in carbon tetrachloride

B) Dilute aqueous potassium permanganate
C) Chlorine in carbon tetrachloride
D) H2SO4
E) IR examination
Answer: E

Section: 2.16, 8.4, 8.11, 8.15, 8.17, 8.19
135) 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
Answer: E

Section: 2.16, 8.17, 8.18, 8.19
136) 2-Pentyne will not react with:
A) H2, Pt
B) Br2
C) NH3
D) H2SO4
E) KMnO4/H2O
Answer: C

Section: 7.13, 8.17, 8.18, 8.19
Question type: True/False
73
137) The reason why anti-Markovnikov addition is seen in the hydration of alkenes using
hydroboration-oxidation conditions is due to steric interactions with the boron group attaching to
the less substituted carbon more easily.
Answer: True

Section: 8.2
138) The yields for an acid catalyzed hydration of an alkene can be increased by using dilute
acid as this will help drive the equilibrium to products.
Answer: True
Topic: Hydration of an Alkene

Section: 8.4
139) Due to the formation of a mercurinium ion in hydration of an alkene using oxymercuration-
demercuration, we see overall anti-product form making this reaction stereospecific.
Answer: False
Topic: Oxymercuration-Demercuration
Section: 8.5
140) In halohydrin formation the reason why the halohydrin is the major product is because the
solvent is more reactive that the bromide nucleophile.
Answer: False
Topic: Halohydrins
Section: 8.13
141) Potassium permanganate is usually a preferred reagent for oxidative cleavage to form
aldehyde, as it is a much milder and less toxic reagent than osmium tetroxide.
74
Answer: False
Topic: Oxidation of Alkenes

Section: 8.15
Question type: fill-in-the-blank
bonds are quite susceptible to reaction with electron-seeking reagents, also referred to as
___.
Answer: electrophiles

Section: 8.1
143) The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is
called ___.
Answer: Markovnikov's Rule

Section: 8.2
144) The introduction of a small amount of a peroxide to a hydrogen halide addition of an alkene
will result in a(n) ___ addition where the hydrogen in the addition appears adds to the carbon
with the ___ number of hydrogens.
Answer: anti-Markovnikov, fewest

Section: 8.2
Question type: Essay
145) 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.
75
HCl
Cl
HCl
most stable
carbocation
Answer:
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.

Section: 8.2
146) 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
H+ + fast I I
+

+ I
I
Answer:
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: 8.2
147) Propose a mechanism for the following transformation accounting for the stereochemistry
76
in the final product:

H+, H2O
OH
Eucalyptol
Ans:
H H
O
H
HO
O
H+
OH

Section: 8.2
148) 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 ___.
Answer: regioselective

Section: 8.2
77
149) Hydroboration-oxidation is a reaction with ___ stereochemistry and ___ regiochemistry.
Answer: syn, anti-Markovnikov

Section: 8.6, 8.7, 8.8
150) 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.
NaOC2H5/C2H5OH, heat
BH3, THF
H2O2, OH
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)
Answer: 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.
Topic: Reaction Sequence

Section: 6.16, 8.6, 8.7, 8.8
151) Even when one or more stereogenic centers are produced as the result of an addition
78
reaction to an alkene, the product is always formed as a racemic mixture. Why is that?
Answer: Because alkenes are planar, and the reagent can add from either face.

Section: 8.3, 8.5, 8.7, 8.11
152) 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 ___.
Answer: stereospecific

Section: 8.12
153) 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.
Answer: stereoselective

Section: 8.12
154) Draw Fischer projection formulas of the major product of the reaction between E-2-methyl-
3-hexene and aqueous Br2.
CH(CH3)2 CH(CH3)2 CH(CH3)2 CH(CH3)2

Br2 HO H H OH H Br Br H
H Br
+ Br H + HO H
+ H OH
H2O
C2H5 C2H5 C2H5 C2H5
Answer:
The reaction takes place with anti stereospecificity. Since the alkene is symmetrically
79
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.

Section: 8.13
155) Predict the major product(s) of the following reaction, giving regiochemical and/or
stereochemical details as relevant.
Br2, H2O
?
OH + OH
Br Br
Answer: H H
The reaction takes place with Markovnikov regioselectivity and anti stereospecificity, giving a
racemic mixture of the halohydrin as the major product.

Section: 8.2, 8.13
156) Carbenes are frequently produced by -elimination reactions. These are reactions in which
the proton being lost and the leaving group are ___.
Answer: both attached to the same carbon

Section: 8.14
157) Neutral divalent carbon compounds are called ___.
Answer: Carbenes

Section: 8.14
158) Predict the structure of product obtained when cis-2-hexene is allowed to react with
Zn/CH2I2.
80
H H
Zn, CH2I2
H + H
Answer:
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.

Section: 8.14
159) Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-2-
methyl-3-hexene and cold, alkaline KMnO4.
CH(CH3)2 CH(CH3)2
cold, dil H OH HO H
KMnO4 H OH + HO H
C2H5 C2H5
Answer:
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol product.

Section: 8.15
160) Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-3-
methyl-3-hexene and cold, alkaline KMnO4.
CH2CH3 CH2CH3
cold, dil H3C OH HO CH3
H OH + HO H
KMnO4
C 2H 5 C 2H 5
Answer:
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol product.

Section: 8.15
161) Predict the product(s) of the oxidation of 2,3,4-trimethyl-1,5-heptadiene with hot, alkaline
KMnO4.
81
OH
hot, alkaline CO + H O + O +
2 2 O
KMnO4 O
Answer: OH

Section: 8.16
162) 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
Answer: 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: 4.16, 8.11, 8.16
163) The decolorization of molecular bromine is often used as a functional group test to detect
the presence of ___.
Answer: carbon-carbon multiple bonds; or, alkenes and alkynes
82
Section: 8.11, 8.17
164) Predict the oxidative product(s) of 2-methyl-6-octyn-2-ene after undergoing ozonolysis.

Answer:
Topic: Oxidative Methods

Section: 4.16, 8.19
165) Devise a retrosynthetic strategy to make the epoxide shown below starting from
cyclohexanol and show the forward reaction with the necessary reagents and significant
intermediates.
Answer:
83
Br
Intramolecular Halohydrin
SN 2 f ormation
O
OH
Dehydration of
Alcohol
OH
OH Br
H+, heat Br2, H2O NaH
O
OH
Topic: Retrosynthetic Analysis

Section: 6.5, 8.13, 8.20
84

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Package title: Solomons Test Bank

Course Title: Solomons 11e

Question type: Multiple choice

A) Both H and S favor product formation.

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?

Topic: Reaction Products

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

Topic: Reaction Products

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

Topic: Reaction Products

Topic: Reaction Products

A) one optically active fraction only

Topic: Reaction Products

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

Topic: Reaction Products

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

Topic: Reaction Products

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

Topic: Reaction Products

Topic: Reaction Products

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

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

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

Topic: Reaction Sequences

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

Topic: Reaction Sequences

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

Topic: Reaction Sequences

20) What is the major product of the following reaction sequence?

Topic: Reaction Sequences

21) In general, when the addition of an unsymmetrical electrophilic reagent to an unsymmetrical

A) the product is statistically favored.

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

Topic: Reaction Products

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

Topic: Reaction Products

27) Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?

Topic: Reaction Products

Topic: Reaction Products

Topic: General Information

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

Topic: Reaction Products

+ enantiomer meso compound

Topic: Reaction Products

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

Topic: Reaction Products

33) What is the major product for the following reaction?

Topic: Reaction Products

34) What is the major product for the following reaction?

Topic: Reaction Products

Topic: Reaction Products

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

Topic: Reaction Sequences