Test Bank for Organic

Chemistry 10th Edition

Carey Giuliano
0073511218
9780073511214
Full download link at:

Test bank: https://testbankpack.com/p/test-bank-

for-organic-chemistry-10th-edition-carey-
giuliano-0073511218-9780073511214/

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 6-2

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1. Identify the nucleophile in the following reaction.

A. CH3Br

¯
B. OH

C. H2O

¯
D. Br

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Easy

Gradable: automatic

Section: 06.05

2.
Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

Identify the leaving group in the following reaction.

6-3

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A. CH3CH2Br

¯
B. HS

¯
C. Br

D. CH3OH

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Easy

Gradable: automatic

Section: 06.02

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

3. Which of the following cannot act as a nucleophile?

A. NH3

6-4

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B. H2O
¯
C. I

D. CH4

Accessibility: Keyboard Navigation

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Easy

Gradable: automatic

Section: 06.05

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

6-5

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 In the SN2 reaction, the "2" stands for
4.

A. two reactants in the reaction.

B.two steps in the reaction.

C.two intermediates in the reaction.

D.bimolecular kinetics for the reaction.

Accessibility: Keyboard Navigation

Bloom's Level: 1. Remember

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

5. Which of the following undergoes a substitution reaction with sodium cyanide in DMSO at the fastest rate?

6-6

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A. CH3CH2F

B. CH3CH2Cl

C. CH3CH2Br

D. CH3CH2I

Accessibility: Keyboard Navigation

Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.02

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

6. 1-Chloro-4-fluorobutane is reacted with one equivalent of sodium iodide in acetone. During the reaction a precipitate
forms. What is the precipitate?

A. FCH2CH2CH2CH2I

B. ClCH2CH2CH2CH2I

C. NaCl

D. NaF

6-7

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 Accessibility: Keyboard Navigation

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Hard

Gradable: automatic

Section: 06.02

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactio

6-8

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7. e rate law for the following reaction is
T
h

A. rate = k[CH3CH2CH2Cl].

B.rate = k[CH3CH2CH2Cl][NaCN].

2
C.rate = k[CH3CH2CH2Cl][NaCN] .

D. rate = k[NaCN].

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Section: 06.04

8.
Subtopic: Substitution reaction mechanisms: SN1 and SN2

6-9

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 T titution and Elimination Reactions
o
pi
c:
Su
Which of the following reacts the fastest by the SN2 mechanism?
bs

A. CH3Br

B. CH3CH2Br

C. (CH3)2CHBr

D. (CH3)3CBr

Accessibility: Keyboard Navigation

Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-10

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9. Give the product(s) of the following reaction.

6-11

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A. A

B. B

C. C

D. a mixture of A and B

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.01

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-12

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10. Which halide ion reacts the fastest with cyclopentylp-toluenesulfonate in ethanol/water?

A. A

B. B

C. C

D. D

6-13

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 Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.05

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

6-14

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11. Which one of the following species forms the strongest ion-dipole attraction with 18-crown-6?

-
A. F

+
B. K

C. Cr2O72-

D. Br2

Bloom's Level: 2. Understand

6-15

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 Chapter: 06

Difficulty: Easy

Gradable: automatic

Section: 06.09

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

12. Identify the major product(s) in the reaction of (R)-2-bromopentane with sodium cyanide in DMSO.

A. (R)-2-cyanopentane

B.(S)-2-cyanopentane

C. racemic mixture of 2-cyanopentane

D. trans-2-pentene

Accessibility: Keyboard Navigation

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

6-16

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 Topic: Substitution and Elimination Reactions

6-17

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13. Which of the following reacts fastest with methanol by the SN1 mechanism?

A. A

B. B

C. C

D. D
6-18

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 Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.06

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

14. A pentacoordinate carbon is a transition state in the _____ mechanism.

A. SN1

B. SN2

C. E1

D. E2

Accessibility: Keyboard Navigation

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Easy

6-19

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 Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-20

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15.What is the leaving group in the following reaction?

-
A. OH

B. H2O

C. CH3CH2+

-
D. C1

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.06

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

16.Which of the following is the rate law for the SN1 mechanism of an alkyl halide with a nucleophile?

6-21

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A.rate = k[alkyl halide]

B.rate = k[nucleophile]

C.rate = k[alkyl halide][nucleophile]

D. rate = k[alkyl halide]2[nucleophile]

Accessibility: Keyboard Navigation

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Easy

Gradable: automatic

Section: 06.06

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-22

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17.
Which of the following does not correctly describe SN2 reactions of alkyl halides?

A. Tertiary halides react faster than secondary halides.

B. Rate of reaction depends on the concentrations of both the alkyl halide and the nucleophile.

C. The mechanism consists of a single step with no intermediates.

D. The transition state species has a pentavalent carbon atom.

Accessibility: Keyboard Navigation

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-23

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18. Identify the substitution product(s) in the following reaction.

6-24

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A. A

B. B

C. C

D. a mixture of A and B

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.07

6-25

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 Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-26

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19. What is the rate limiting step in the following reaction?

A. A

B. B

C. C

D. D

6-27

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 Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.06

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-28

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20.
The mechanism of the following reaction is

A.SN1.

B.SN2.

C.SN1/2.

D.SN1-2.

6-29

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 Bloom's Level: 2.
Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Subtopic: Substitution
reaction mechanisms:
SN1 and SN2

Topic: Substitution
and Elimination
Reactions

6-30

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21. Which of the following reacts the slowest with sodium cyanide, NaCN?

A. A

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B. B

C. C

D. D

Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.04

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

6-32

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22. How would you synthesize the following compound starting with optically pure (R) or (S)-2-butanol?

A. (1) (R)-2-butanol + TsCl (2) NaCN/DMSO

B. (1) (S)-2-butanol + TsCl (2) NaCN/DMSO

C. (1) (S)-2-butanol + H2SO4 (heat) (2) HBr (3) NaCN/DMSO

D. (R)-2-butanol + NaCN/DMSO

23.

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 Difficulty: Hard

Blo
om' Gradable: automatic
s
Lev
Section: 06.11
el:
4.
Ana
Subtopic: Substitution reaction mechanisms: SN1 and SN2
lyze

Topic: Substitution and Elimination Reactions

Cha
pter
: 06

Starting with optically pure (R) or (S)-2-butanol which method below would give the best yield of the following ether?

A. (1) (R)-2-butanol + TsCl (2) CH3ONa

B. (1) (S)-2-butanol + TsCl (2) CH3ONa

C. (1) (R)-2-butanol + Na (2) CH3I

D. (1) (S)-2-butanol + Na (2) CH3I

6-34

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 Bloom's Level: 5. Evaluate

Chapter: 06

Difficulty: Hard

Gradable: automatic

Section: 06.11

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-35

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24. Which of the following conditions favor the SN1 mechanism as opposed to the SN2 mechanism?

I. tertiary alkyl halide

II. primary alkyl halide

III. polar solvent

A. only I

B. only II

C. I and III

D. II and III

Accessibility: Keyboard Navigation

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Easy

Gradable: automatic

Section: 06.06

Subtopic: Factors affecting substitution reactions

6-36

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 Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

25. The species shown below represents the transition state for the

A. reaction of 1-propanol with HBr.

-
B. reaction of 1-bromopropane with OH .

C. elimination of HBr from 1-bromopropane.

D. addition of HBr to propene with peroxides.

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

6-37

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 Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-38

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26. The species shown below represents the transition state for the

A. reaction of 1-propanol with HBr.

-
B. reaction of 1-bromopropane with OH .

C. addition of HOBr to 1-propene.

D. addition of HBr to propene with peroxides.

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.06

Subtopic: Substitution reaction mechanisms: SN1 and SN2

6-39

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 Topic: Substitution and Elimination Reactions

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27. Which of the following is the double substitution product of the reaction below?

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A. A

B. B

C. C

D. D

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Hard

Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-42

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28. the following in decreasing order of leaving group ability.
Ra
nk

A. I > III > IV > II

B.I > III > II > IV

C.III > II > I > IV

D. II > I > III > IV

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

6-43

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 Section: 06.02

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

29. A limitation of substitution reactions with alkyl halides is that a competing elimination reaction often occurs. Consider the
reaction below. One of the products results from the substitution reaction, and the other product results from the
elimination reaction. What is being removed from the alkyl halide in the elimination reaction?

A. Br

B. OCH3

C. Br and OCH3

D. Br and H

Bloom's Level: 2. Understand

Chapter: 06

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 Difficulty: Medium

Gradable: automatic

Section: 06.12

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-45

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30. Which of the following mechanistic steps is the most likely route for the formation of the cyclic ether shown?

A. A

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B. B

C. C

D. D

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Hard

Gradable: automatic

Section: 06.03

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

31. In which of the solvents below would the reaction shown take place at the fastest rate?

A. ethanol

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B. acetic acid

C. dimethyl sulfoxide

D. water

Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.09

Subtopic: Factors affecting substitution reactions

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-48

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32. Which one of the following correctly describes the reaction below?

6-49

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McGraw-Hill Education.
A. A

B. B

C. C

D. D

Bloom's Level: 2. Understand

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-50

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33. Which of the following undergoes SN1 solvolysis in ethanol/water at the fastest rate?

A. A

B. B

C. C

D. D

Bloom's Level: 4. Analyze

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.02

Subtopic: Factors affecting substitution reactions

Topic: Substitution and Elimination Reactions

6-51

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34. The major product of the following reaction is an alcohol. Which of the following best describes this reaction?

A. SN2 with inversion of configuration

B. SN2 with racemization

C. SN1 with inversion of configuration

D. SN1 with racemization

Bloom's Level: 2. Understand

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 Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.07

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-53

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35. The major product(s) of this reaction would be

A. only (R)

B. only (S)

C. (R) and (S)

D. achiral

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.07

Subtopic: Substitution reaction mechanisms: SN1 and SN2

6-54

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 Topic: Substitution and Elimination Reactions

36. The major product(s) of this reaction would be

A. only (R)

B. only (S)

C. (R) and (S)

D. achiral

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

6-55

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 Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-56

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37. The major product(s) of this reaction would be

A. only (R)

B. only (S)

C. (R) and (S)

D. achiral

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.03

Subtopic: Substitution reaction mechanisms: SN1 and SN2

6-57

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 Topic: Substitution and Elimination Reactions

38. The major product expected from the reaction below would be

A. A

B. B

C. C

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D. D

Bloom's Level: 3. Apply

Chapter: 06

Difficulty: Medium

Gradable: automatic

Section: 06.07

Subtopic: Substitution reaction mechanisms: SN1 and SN2

Topic: Substitution and Elimination Reactions

6-59

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 Category # of Questions

Accessibility: Keyboard Navigation 10

Bloom's Level: 1. Remember 1

Bloom's Level: 2. Understand 20

Bloom's Level: 3. Apply 8

Bloom's Level: 4. Analyze 8

Bloom's Level: 5. Evaluate 1

Chapter: 06 38

Difficulty: Easy 7

Difficulty: Hard 5

Difficulty: Medium 26

Gradable: automatic 38

Section: 06.01 1

Section: 06.02 5

Section: 06.03 12

Section: 06.04 2

Section: 06.05 3

Section: 06.06 6

Section: 06.07 4

Section: 06.09 2

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Section: 06.11 2

Section: 06.12 1

Subtopic: Factors affecting substitution reactions 18

Subtopic: Substitution reaction mechanisms: SN1 and SN2 28

Topic: Substitution and Elimination Reactions 38

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