Test Bank For Organic Chemistry Standalone Book 10th Edition

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Test Bank for Organic Chemistry – Standalone10th Edition

Test Bank for Organic Chemistry – Standalone10th


Edition

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1. Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why?

A. The double bond is much stronger and thus more difficult to rotate.
B.Overlap of the two 2p orbitals of the π bond would be lost.
C. The shorter bond length of the double bond makes it more difficult for the attached groups to pass each other.
D. Overlap of the sp2orbitals of the carbon-carbon σ bond would be lost.

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Easy
Gradable: automatic
Section: 07.03
Subtopic: Physical properties of alkenes
Topic: Alkenes

2. What is the IUPAC name of the following compound?

A. 2,5-dimethyl-1-hexene
B. 2,5-dimethyl-2-hexene
C. 1,4-dimethyl-1-hexene
D. 2,5-dimethyl-5-hexene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.01
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

7-1
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
3.
What is the IUPAC name of the following compound?

A. 2-methyl-3-propyl-2-pentene
B.2,3-dimethyl-2-hexene
C.4-ethyl-5-methyl-4-hexene
D. 4-methyl-3-propyl-3-pentene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.01
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

4. What is the IUPAC name of the following compound?

A. 3-ethyl-8-methyl-3-nonene
B. 1,1-diethyl-6-methyl-3-heptene
C. 7-ethyl-2-methyl-6-nonene
D. 3-ethyl-7-isopropyl-3-octene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.01
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

7-2
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
5. How many isomeric alkenes of formula C4H8, including stereoisomers, are possible?

A. two
B. three
C. four
D. five

Accessibility: Keyboard Navigation


Bloom's Level: 3. Apply
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.03
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

6. How many isomeric alkenes of formula C5H10, including stereoisomers, are possible?

A. three
B. four
C. five
D. six

Accessibility: Keyboard Navigation


Bloom's Level: 3. Apply
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.03
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

7. What is the IUPAC name of the following compound?

A. 3-bromo-2-methylcyclohexene
B.1-bromo-2-methyl-2-cyclohexene
C.6-bromo-1-methylcyclohexene
D. 2-bromo-1-methylcyclohexene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.01
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

7-3
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
8. What is the IUPAC name of the following compound?

A. 3-ethyl-propyl-1-heptene
B. 4,6-diethyl-1-octene
C. ethyl-3-vinyloctane
D. 3,5-diethyl-1-octene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.01
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

9. Which of the following alkenes exhibit E-Z isomerism?

A. I and II
B. I and III
C. II and IV
D. I, II, and III

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.04
Subtopic: IUPAC Nomenclature of alkenes
Subtopic: Physical properties of alkenes
Topic: Alkenes

7-4
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
10. Which of the following alkenes exhibit E-Z isomerism?

I. 1-chloropropene II. 2-chloropropene III. 3-chloropropene

A. only I
B. I and II
C. II and III
D. I and III

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.04
Subtopic: IUPAC Nomenclature of alkenes
Subtopic: Physical properties of alkenes
Topic: Alkenes

11. What is the IUPAC name of the following compound?

A.
(E)-3-bromo-1-fluoro-2-methylpropene

B.
(Z)-3-bromo-1-fluoro-2-methylpropene

C.
(E)-1-bromo-3-fluoro-2-methylpropene

D.
(Z)-1-bromo-3-fluoro-2-methylpropene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.04
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

7-5
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
12. Which of the following C6H12 isomers has the highest heat of combustion?

A. 1-hexene
B. trans-3-hexene
C. cis-3-hexene
D. 2-methyl-2-pentene

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.06
Subtopic: Relative stability of alkenes
Topic: Alkenes

13.Identify the major organic product expected from the acid-catalyzed dehydration of 2-methyl-2-pentanol.

A. 2-methyl-1-pentene
B.2-methyl-2-pentene
C.3-methyl-1-pentene
D. cis-3-methyl-2-pentene

Accessibility: Keyboard Navigation


Bloom's Level: 3. Apply
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.10
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-6
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
14.
Which alcohol below would undergo acid-catalyzed dehydration most readily?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.12
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

15. What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-2-propanol?

A. Protonation of the alcohol to form an oxonium ion.


B. Loss of water from the oxonium ion to form a carbocation.
C.Loss of a β-hydrogen from the carbocation to form an alkene.
D.The simultaneous loss of a β-hydrogen and water from the oxonium ion.

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Easy
Gradable: automatic
Section: 07.12
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-7
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
16. Which of the following carbocations is(are) likely to undergo a rearrangement?

A. only I
B. I and III
C. II and III
D. I, II, and III

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.13
Subtopic: Carbocations
Topic: Substitution and Elimination Reactions

7-8
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
17. Predict the major product of the following reaction.

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.13
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

18. Which of the following expressions is the experimentally observed rate law for an E2 reaction of an alkyl halide?

A. rate = k[RX]
B. rate = k[RX][base]
2
C. rate = k[RX]
D. rate = k[base]

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Easy
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-9
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
19. Which of the following most readily undergoes an E2 reaction with sodium ethoxide (NaOCH2CH3)?

A. (CH3)3CF
B. (CH3)3CCl
C. (CH3)3CBr
D. (CH3)3CI

Accessibility: Keyboard Navigation


Bloom's Level: 4. Analyze
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

20. How many isomeric alkenes are possible, including stereoisomers, in the following reaction?

A. two
B. three
C. four
D. five

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-10
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
21. In the dehydrohalogenation of 2-bromobutane, which conformation below leads directly to the formation of cis-2-
butene?

A. only I
B. only II
C. only III
D. I and II

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

.
22 Which of the following cannot undergo an E2 reaction?

A. only I
B. only II
C. only III
D. I and III

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-11
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
23. Which of the following would you predict to be the best method for doing the following conversion with the highest
yield?

A. H2SO4, heat
B. NaOCH2CH3
C. H3PO4
D. (1) PBr3 (2) KOC(CH3)3

Bloom's Level: 5. Evaluate


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.14
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

24. When a strong base is used in the elimination reaction of an alkyl halide the mechanism, in general, is

A. E1.
B. E2.
C. E1 for tertiary halides, E2 for primary and secondary halides.
D. E2 for tertiary halides, E1 for primary and secondary halides.

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-12
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
25. Which of the following sets of conditions most favors the E1 mechanism?

A. when the alkyl halide is tertiary and the base is a weak base
B. when the alkyl halide is tertiary and the base is a strong base
C. when the alkyl halide is primary or secondary and the base is a weak base
D. when the alkyl halide is primary or secondary and the base is a strong base

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-13
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
26. Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-14
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
27. What is the first step in the mechanism of the dehydration reaction of a tertiary alcohol with sulfuric acid to form an
alkene?

-
A.the loss of OH to form a carbocation
B. the protonation of the hydroxyl group
C. the loss of the proton from the hydroxyl group to give an alkoxide ion
D.the removal of a β-hydrogen from the alcohol

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Easy
Gradable: automatic
Section: 07.09
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

28. Which of the following does not give 1,2-dimethylcyclohexene as one of the acid-catalyzed dehydration products?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.13
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-15
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
29. Including E-Z isomers, how many E2 products are possible in the following reaction?

A. one
B. two
C. three
D. four

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

30. Which of the following compounds gives a single E2 product on reaction with sodium ethoxide, NaOCH 2CH3?

A. I and II
B. I and III
C. II and III
D. I, II, and III

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-16
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
31. Which of the following will give 2-methyl-1-butene as the only alkene product on treatment with KOC(CH3)3 in
dimethyl sulfoxide?

A. 2-bromo-3-methylbutane
B. 2-bromo-2-methylbutane
C. 1-bromo-3-methylbutane
D. 1-bromo-2-methylbutane

Accessibility: Keyboard Navigation


Bloom's Level: 3. Apply
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.14
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

32. If the following E2 reaction proceeds through an antiperiplanar transition state, what product or products are
expected?

A. only 1-methylcyclohexene
B. only 3-methylcyclohexene
C. only 4-methylcyclohexene
D. equal amounts of 1-methylcyclohexene and 3-methylcyclohexene

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-17
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
33. Which of the following stereoisomers gives the exclusive E2 product shown?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.16
Topic: Substitution and Elimination Reactions

7-18
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
34. Zaitsev's rule can be used to predict the major product for which of the following reactions?

A. 2-methylpentane + Br2(with light)


B. 2-bromo-2-methylpentane + NaOCH2CH3 (in ethanol)
C. 2-methyl-2-pentanol + PBr3
D. 2-methyl-2-pentanol + HCl

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Easy
Gradable: automatic
Section: 07.10
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

35. The acid-catalyzed dehydration of the alcohol shown below gives a major product which results from a carbocation
rearrangement. Identify this major product.

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.13
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Subtopic: Substitution reactions SN1 and SN2
Topic: Substitution and Elimination Reactions

7-19
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
36.
Considering the SN1, SN2, E1, and E2 mechanisms, the energy diagram shown below corresponds to

A. only the SN1 mechanism.


B.both the SN1 and E1 mechanisms.
C.only the SN2 mechanism.
D.both the SN2 and E2 mechanisms.

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Substitution reactions SN1 and SN2
Topic: Substitution and Elimination Reactions

37. How many different E2 products are expected in the reaction of 3-bromo-1,1-dimethylcyclohexane with
NaOCH2CH3?

A. only 1
B. 2
C. 3
D. 4

Accessibility: Keyboard Navigation


Bloom's Level: 3. Apply
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-20
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
38. Which one of the following compounds cannot undergo an E2 reaction?

A. 1-bromo-2,2-dimethylbutane
B. 1-bromo-3,3-dimethylbutane
C. 1-bromo-2,3-dimethylbutane
D. 2-bromo-2,3-dimethylbutane

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

39. Which of the following compounds gives 4,4-dimethylcyclohexene as the exclusive E2 product?

A. A
B. B
C. C
D. both A and B

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.16
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-21
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
40. How many stereoisomers are possible for the following diene?
CH3CH=CHCH2CH2CH=CHCH2CH2CH3

A. only 1
B. two
C. three
D. four

Accessibility: Keyboard Navigation


Bloom's Level: 3. Apply
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.03
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

7-22
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
41. Based on Zaitsev's rule, which of the following is the major product of the reaction below?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-23
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
42. Which of the alkenes below has the Z-configuration?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.04
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

43. Which alkene of formula C5H10 gives off the least heat (per mol) when burned?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.06
Subtopic: Relative stabilities of alkenes
Topic: Alkenes

7-24
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
44. When a C=C is present in a molecule, what is the minimum number of atoms that must lie in a single plane?

A. 2
B. 4
C. 6
D. 8

Accessibility: Keyboard Navigation


Bloom's Level: 2. Understand
Chapter: 07
Difficulty: Easy
Gradable: automatic
Section: 07.02
Subtopic: Physical properties of alkenes
Topic: Alkenes

45. If you wanted to make compound III, starting with compound I or II, what would you do?

A.React I with H2SO4.


B.React II with NaOEt.
C.Either of the reactions in A or B above would work.
D.Neither of the reactions in A or B above would work.

Bloom's Level: 4. Analyze


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.15
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-25
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
46. Considering E2 reactions involving the labeled deuterium atoms, which compound would have the slowest reaction
rate?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand


Bloom's Level: 3. Apply
Bloom's Level: 4. Analyze
Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.17
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-26
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
47.
Which of the following bases works best to maximize the E2 product in the reaction shown below?

A. KOCH2CH3
B.NaOCH2CH3
C.NaOC(CH3)3
D.NaOH

Bloom's Level: 4. Analyze


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-27
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
48. In the solvolysis of t-butyl chloride, a minor product is 2-methylpropene, which results from the:

-
A. E2 mechanism with OH acting as the base.
B.E2 mechanism with H2O acting as the base.
-
C.E1 mechanism with OH acting as the base.
D.E1 mechanism with H2O acting as the base.

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Factors affecting elimination reactions
Topic: Substitution and Elimination Reactions

7-28
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
49. What would be the proper name of the molecule below?

A. (E)-2-ethyl-2-butene
B.(Z)-3-methyl-3-pentene
C.(E)-3-methyl-2-pentene
D.(Z)-2-isohexene

Bloom's Level: 4. Analyze


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.04
Subtopic: IUPAC Nomenclature of alkenes
Topic: Alkenes

50. Identify the mechanistic pathways, respectively, for the products in the following reaction.

A. E1, SN1
B. E1, SN2
C. E2, SN1
D. E2, SN2

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Substitution reaction mechanisms: SN1 and SN2
Topic: Substitution and Elimination Reactions

7-29
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
51. Identify the mechanistic pathways, respectively, for the products in the following reaction.

A. E1, SN1
B. E1, SN2
C. E2, SN1
D. E2, SN2

Bloom's Level: 2. Understand


Chapter: 07
Difficulty: Medium
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Substitution reaction mechanisms: SN1 and SN2
Topic: Substitution and Elimination Reactions

7-30
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McGraw-Hill Education.
52. What is the major product in the following reaction?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply


Chapter: 07
Difficulty: Hard
Gradable: automatic
Section: 07.19
Subtopic: Elimination reaction mechanisms: E1 and E2
Subtopic: Substitution reaction mechanisms: SN1 and SN2
Topic: Substitution and Elimination Reactions

7-31
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
Category # of Questions
Accessibility: Keyboard Navigation 17
Bloom's Level: 2. Understand 22
Bloom's Level: 3. Apply 24
Bloom's Level: 4. Analyze 7
Bloom's Level: 5. Evaluate 1
Chapter: 07 52
Difficulty: Easy 6
Difficulty: Hard 12
Difficulty: Medium 34
Gradable: automatic 52
Section: 07.01 5
Section: 07.02 1
Section: 07.03 4
Section: 07.04 5
Section: 07.06 2
Section: 07.09 1
Section: 07.10 2
Section: 07.12 2
Section: 07.13 4
Section: 07.14 2
Section: 07.15 8
Section: 07.16 8
Section: 07.17 1
Section: 07.19 7
Subtopic: Carbocations 1
Subtopic: Elimination reaction mechanisms: E1 and E2 33
Subtopic: Factors affecting elimination reactions 29
Subtopic: IUPAC Nomenclature of alkenes 13
Subtopic: Physical properties of alkenes 4
Subtopic: Relative stabilities of alkenes 1
Subtopic: Relative stability of alkenes 1
Subtopic: Substitution reaction mechanisms: SN1 and SN2 3
Subtopic: Substitution reactions SN1 and SN2 2
Topic: Alkenes 17
7-32
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.
Test Bank for Organic Chemistry – Standalone10th Edition

Topic: Substitution and Elimination Reactions 35

7-33
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McGraw-Hill Education.
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