Chapter 7 Haloalkanes

Multiple Choice
1. Which of the following structures have the correct IUPAC name? (Sec. 7.2)

Cl
H

C CH CH CH
2
2
3
CH3

CH3
F

R-2-chloropentane
I

R-4-fluoro-4-methylcyclohexene
II

H3CO
Br

CH3
Cl

Br
H

S-2-chloro-2-fluorobutane
IV

I, II
III, IV
I, III
II, IV

2. Which of the following structures have correct common names? (Sec. 7.2)

H3C
H2C

CHCH2F

CHCH2Br
H3C

allyl fluoride
I

isobutyl bromide
II
I

HCCl3
methylene chloride
III
a)
b)
c)
d)

CH2CH3

OCH3

meso-1,2-dibromo-1,2-dimethoxyethane
III
a)
b)
c)
d)

H3C

CH CH2CH3

isopropyl iodide
IV

I, II
III, IV
I, III
II, IV

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Chapter 7 Haloalkanes

3. Which of the following compounds are secondary halides? (Sec. 7.6)

I) Isobutyl bromide
a)
b)
c)
d)

II) 2-iodobutane

III) isopropyl fluoride

IV) neopentyl chloride

I, II
III, IV
II, III
I, IV

4. Which compounds are primary halides? (Sec. 7.6)

H
H3C

CH3

CH3
H3C

CH3

Cl

H3C

CH2 CBr3

FH2C

CH3

II

III

IV

I, II
III, IV
II, III
I, IV

5. Which of the following halides is prepared from the following reactions? (Sec. 7.1, 5.3)

HBr

Br
Br

Br
Br

Br
a)

b)

c)

d)

6. Which is the best reaction condition for preparing 2-iodohexane from 1-hexene? (Sec. 7.1, 5.3)
a)
b)
c)
d)

CH2 CH

CH3

I
a)
b)
c)
d)

CH3

I2 / CCl4
HI
NaI
HIO4

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Chapter 7 Haloalkanes

7. Arrange the nucleophiles in order of increasing reactivity (least first). (Sec. 7.6)

NH3

H2O

OH

II

III

a)
b)
c)
d)

CH3O
IV

I, IV, II, III

IV, II, I, III
II, I, III, IV
IV, III, I, II

8. Arrange the nucleophiles in order of increasing reactivity (least first). (Sec. 7.6)

O
H3CCO

H3CO

Br

H2O

II

III

IV

I
a)
b)
c)
d)

III, II, I, IV
IV, I, II, III
I, III, II, IV
III, I, IV, II

9. Arrange the leaving groups in order of increasing leaving group ability (least first). (Sec. 7.6)

O
H3CCO
I
a)
b)
c)
d)

H3CO

Br

HO

II

III

IV

I, III, II, IV
III, I, IV, II
VI, II, I, III
IV, III, II, I

10. Arrange the leaving groups in order of increasing leaving group ability (least first). (Sec. 7.6)

a)
b)
c)
d)

Cl

Br

II

III

IV

IV, I, III, II
III, I, IV, II
II, IV, I, III
II, III, I, IV

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Chapter 7 Haloalkanes
11. Arrange the alkyl halides in order of increasing reactivity in an SN2 reaction with KI in acetone (least first).
(Sec. 7.6-7.7)

Cl
CH2CH2Br

Cl

Br

CCH3
CH3

I
a)
b)
c)
d)

II

III

I, IV, III, II
IV, I, III, II
II, III, I, IV
III, II, IV, I

12. Which are optimum conditions for an SN2 reaction? (Sec. 7.6-7.7)

I.

II.

acetone

CH2Cl

NaSH

Cl

CH3OH

CH3S Na

NaI

CH3
III.

IV.

a)
b)
c)
d)

Cl

CH2Br

I, II
II, III
III, IV
I, IV

78

H2O

DMSO

DMSO

IV

Chapter 7 Haloalkanes

13. Which nucleophilic substitution reactions will proceed? (Sec. 7.6-7.7)

I. NaCl + CH3CH2OH

II. NH3

acetone

Br

ethanol

III. CH3CH2O + CH3CH2CH2Cl ethanol

IV. LiCl + CH4
a)
b)
c)
d)

acetone

I, II
II, III
III, IV
I, IV

14. Which reactions will proceed with inversion of configuration? (Sec. 7.6-7.7)

OCH2CH3
R-2-bromohexane
CH3CH2OH

S-2-iodobutane

OH
R-3-bromo-3-methylhexane
CH3CH2OH
III.

R-2-bromohexane
IV.

I, II
III, IV
II, III
I, IV

15. Which solvents are polar aprotic? (Sec. 7.6)

I) DMSO
II) H2O
III) Acetone
IV) Formic acid
a)
b)
c)
d)

acetone

II.

I.

a)
b)
c)
d)

NaSCH3

II, III
III, IV
I, III
II, IV

79

CH3OH
heat

Chapter 7 Haloalkanes
16. Arrange the alkyl halides in order of increasing rate of solvolysis (slowest first)? (Sec. 7.6)

CH3
H3C

H3CH2C

CCl

CHCl

H3CH2C

CH3
I
a)
b)
c)
d)

H3C

CHCl

H3C
III

II

IV, III, II, I

I, II, III, IV
III, II, I, IV
II, III, I, IV

17. Which conditions are optimum for an SN1 reaction? (Sec. 7.6-7.7)

a)

CH3CH2Cl

NaCN

CHCl

CH3OH

CH3CH2CH2Br

NaSH

NaCN

acetone

H3C
b)

H2O

H3C
c)

DMSO

CH3
d)

H3C

CCl

DMSO

CH3
18. Which solvents are polar protic? (Sec. 7.6)
I) ethanol
II) hexane
III) DMSO
IV) water
a)
b)
c)
d)

III, IV
II, III
I, IV
I, III

80

CH3CH2CH2Cl

IV

Chapter 7 Haloalkanes

19. Which statements apply to an SN1 reaction? (Sec. 7.6)

I) The rate limiting step of the reaction involves the alkyl halide and the nucleophile.
II) The order of reactivity is methyl > 1>2>3.
III) The rate limiting step of the reaction involves only the alkyl halide.
IV) There is an intermediate carbocation.
a)
b)
c)
d)

I, II
III, IV
I, IV
III

20. Which statements apply to an SN2 reaction? (Sec. 7.6)

I) The rate limiting step of the reaction involves the alkyl halide and the nucleophile.
II) The order of reactivity is methyl > 1>2>3.
III) The rate limiting step of the reaction involves only the alkyl halide.
IV) There is an intermediate carbocation.
a)
b)
c)
d)

I, II
III, IV
I, IV
II, IV

21. Which conditions are optimum for an E2 reaction? (Sec. 7.8-7.9)

a)

CH3I

CH3
b) CH3CHCl

CH3
+

CH3CO K

CH3OH

CH3O

CH3
d) CH3CHCH2Br

DMSO

CH3

CH3
c) CH3CHCH2Cl

DMSO

H2O

H2O

22. What is the major product from an elimination reaction starting with 2-bromopentane? (Sec. 7.8-7.9)
a)
b)
c)
d)

1-pentene
cis-2-pentene
trans-2-pentene
a mixture of cis and trans-2-pentene

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Chapter 7 Haloalkanes

23. Which alkyl halide leads to the product shown, in an E2 reaction? (Sec. 7.8-7.9)

CH2

Cl

CH2Cl

CH3
CH3

a)

b)

CH3
c)

d)

Cl

Cl

24. Which statements are true for an E1 reaction? (Sec. 7.9)

I) The rate limiting step of the reaction involves only the alkyl halide.
II) The rate limiting step of the reaction involves the alkyl halide and the base.
III) There is an intermediate carbocation.
IV) The order of reactivity is 1>2>3.
a)
b)
c)
d)

I, III
II
I, III, IV
II, IV

25. Which conditions are best for preparing isopropyl methyl ether? (Sec. 7.10)

H3C
a)

b)

Na OCH3

Na OCH

d)

CHBr

H3C

CH3
CH3

c)

CH3OH

CH3OH

CH3Br
H3C

CHBr

heat

CHOH

acid
catalysis

H3C
H3C
H3C

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Chapter 7 Haloalkanes
Fill in the Blank
1. The major product of the following reaction is,

KSCH3
Cl

DMSO
(Sec. 7.6)

2. The major product of the following reaction is,

KOH
Br

H2O

(Sec. 7.6)

3. The major product of the following reaction is,

NH3
H

(Sec. 7.6)

4. The major product of the following reaction is,

NaOCH2CH3
CH3CH2OH

(Sec. 7.9)

5. The major product of the following reaction is,

H2O
H Br

(Sec. 7.6)

6. The reagent needed to complete the following reaction is,

Cl
(Sec. 7.9)

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Chapter 7 Haloalkanes

7. The reagent needed to complete the following reaction is,

Br

OH

(racemic)
(Sec. 7.6)
8. The reagent needed to complete the following reaction is,

Br

H3CO

OCH3

+
(Sec. 7.6)
9. The starting material needed to complete the following reaction is,

KI
I
CH3CH2OH
(Sec. 7.6)
10. The starting material needed to complete the following reaction is,

HS

NaSH
acetone

(Sec. 7.6)

True-False
1. Polar aprotic solvents favor SN1 reactions. (Sec. 7.6)
2. The order of SN1 reactivity of the following alkyl halides are listed in decreasing order. (Sec. 7.6)

Cl > H3C Cl

>

Cl

>

Cl

3. The order of SN2 reactivity of the following alkyl halides are listed in decreasing order. (Sec. 7.6)

Br >

>

F >

Cl

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Chapter 7 Haloalkanes

4. The following nucleophiles are listed in decreasing order of reactivity in an SN2 reaction. (Sec. 7.6)

I- > Br- > Cl-

> F-

5. The following nucleophiles are listed in decreasing order of reactivity in an SN2 reaction. (Sec. 7.6)

F- > HO- > H2N6. The name of the following compound is cis- (1R,2S)-1-chloro-2-bromocyclohexane. (Sec. 7.2)

Cl
Br

7. The name of the following compound is R, E - 4-bromo-2-pentene. (Sec. 7.2)

Br

8. The major product of the reaction of R-2-bromobutane with sodium iodide in acetone is S-2-iodobutane.
(Sec. 7.6)
9. The major product of the reaction of R-2-bromobutane with water is a racemic alcohol. (Sec. 7.6)
10. The major product of the reaction of bromocyclohexane and potassium t-butoxide in water is an ether.
(Sec. 7.6)

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Chapter 7 Haloalkanes
Answers
Multiple Choice
1. c
2. a
3. c
4. b
5. a
6. b
7. c
8. b
9. c
10. a
11. d
12. d
13. b
14. a
15. c
16. a
17. b
18. c
19. b
20. a
21. b
22. c
23. c
24. a
25. b
Fill in the Blank
1.

H SCH3
2.

H OH
3.

H2N

86

Chapter 7 Haloalkanes

4.

5.

+
HO H

H OH

6. base
7. H2O
8. HOCH3
9.

Br or

Cl

10.

Cl

(or Br, -I)

True-False
1. F
2. F
3. F
4. T
5. F
6. F
7. T
8. T
9. T
10. F

87