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Chapter Twelve MULTIPLE CHOICE QUESTIONS Topic: General Carbonyl Information Section: 12.1 Difficulty Level: Easy 1. Which of the following resonance structures is not a significant contributor to the hybrid for the carbonyl group? C

O

I

A) B) C) D) E)

C

O

C

II

O

III

I II III Neither II nor III is important. All are significant contributors. Ans: B

Topic: General Carbonyl Information Section: 12.1 Difficulty Level: Easy 2. When nucleophilic addition to a carbonyl group occurs, the carbon attacked undergoes this hybridization change: A) sp2  sp3 B) sp  sp2 C) sp  sp3 D) sp3  sp2 E) sp2  sp Ans: A

799

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Easy 3. The following transformation would be considered a(n)? OH

A) B) C) D) E)

O

reduction oxidation addition elimination rearrangement Ans: B

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Easy 4. The following transformation would be considered a(n)?

A) B) C) D) E)

reduction oxidation addition elimination rearrangement Ans: A

800

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Easy 5. The following transformation would be considered a(n)? O

O

H

A) B) C) D) E)

OH

reduction oxidation addition elimination rearrangement Ans: B

Topic: Redox Section: 12.2 Difficulty Level: Easy 6. A) B) C) D) E)

Which reaction is an oxidation? RCHO  RCO2H RCH2OH  RCHO RCH2OH  RCO2H None of these All of these Ans: E

801

Topic: Synthetic Strategy, Redox Section: 12.2 Difficulty Level: Easy 7. Which product is formed from the following transformation: O

1. LAH ?

O

2. H3O+

A) O OH

B) HO OH

C) O

D) H HO O

E) O

OCH3

Ans: B

Topic: Redox Section: 12.2 Difficulty Level: Easy 8. A) B) C) D)

Which of these transformations cannot be classified as a reduction? RCH2Cl  RCH3 RCH=CH2  RCH2CH3 RCOOH  RCH2OH O

RCH2OH + R'OH E) All of these are reductions. Ans: E RCOR'

802

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 9. List the following compounds in order of increasing level of oxidation: OH

III

II

I

A) B) C) D) E)

O

I, II, III I, III, II II, I, III III, II, I III, I, II Ans: E

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 10. List the following compounds in order of increasing level of oxidation: OH

II

I

A) B) C) D) E)

NH

III

I, II, III I, III, II II, I, III III, I, II III, II, I Ans: D

803

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 11. List the following compounds in order of increasing level of oxidation: Cl

NH2

III

II

I

A) B) C) D) E)

NH

I, II, III III, II, I II, I, III III, I, II I, III, II Ans: A

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 12. List the following compounds in order of increasing level of oxidation: O

II

I

A) B) C) D) E)

III

I, II, III III, II, I II, I, III III, I, II I, III, II Ans: D

804

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 13. List the following compounds in order of increasing level of oxidation: CH3CH2NH2 CH3CN H2NCH2CH2NH2 I

II

A) B) C) D) E)

III

I, II, III III, II, I II, I, III III, I, II I, III, II Ans: B

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 14. List the following compounds in order of increasing level of oxidation: CH2Cl2 CH3OH HCOOH I

II

A) B) C) D) E)

III

I, II, III III, II, I II, I, III III, I, II I, III, II Ans: D

805

Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 15. The following transformation would be considered a(n)? CH3Cl CH 3MgCl A) reduction B) oxidation C) addition D) elimination E) rearrangement Ans: A Topic: Oxidation-Reduction Section: 12.2 Difficulty Level: Medium 16. List the following alkyl halides in order of increasing ease of Grignard formation: RF RCl RBr RI II

I

A) B) C) D) E)

III

IV

I, II, III, IV III, I, II , IV IV, II, I, III III, I, IV, II I, IV, III, II Ans: C

Topic: Synthetic Strategy, Redox Section: 12.2 Difficulty Level: Medium 17. Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CHO into CH3CH2CH2CH2CH2CH2CH2OH? A) KMnO4 B) NaBH4 C) Br2 in CCl4 D) H2, Ni E) Two of the above Ans: D

806

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Easy 18. Which of these compounds will not be reduced by LiAlH4? A) CH3CH2CH2CH=CH2 H B) C)

CH3CH 2CH2C O

O

D)

CH3CH2CH2COH O

E)

CH3CH 2CH2COCH 3 O CH3CH2CH2CCH3

Ans: A Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Easy 19. Which reagent(s) is/are capable of reducing the following ester to a primary alcohol ? O O

A) B) C) D) E)

LiAlH4 / ether NaBH4 / H2O Na / C2H5OH H2 / Ni, atmospheric pressure All can be used successfully. Ans: A

807

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Easy 20. Which of the reagents listed below would efficiently accomplish the transformation of 3-methyl-3-cyclopentenone into 3-methyl-3-cyclopentenol? O

OH

? A) B) C) D) E)

i) LiAlH4; ii) H2O NaBH4,H2O H2, Pd A) and B) A), B) and C) of the above Ans: D

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Easy 21. Which of the reagents listed below would efficiently accomplish the transformation of ethyl-3-pentenoate into 3-penten-1-ol? O HO ? O

A) B) C) D) E)

i) LiAlH4; ii) H2O NaBH4,H2O H2, Pd A) and B) A), B) and C) of the above Ans: A

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Easy

22. A) B) C) D) E)

Which reagent(s) would you use to convert CH3(CH2)6CO2H to CH3(CH2)6CH2OH? NaBH4/H2O LiAlH4/ether, then H3O+ PCC/CH2Cl2 Zn, H3O+ H2, Pt Ans: B

808

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Easy 23. Which of these compounds cannot be reduced by sodium borohydride? H A) B)

(CH 3 )2CHC O

C)

CH3CH2CCH3 O

O

C6H5COH

D)

O CH3(CH2 ) 4COCH3

E) Neither C) nor D) can be reduced. Ans: E Topic: Redox, Reaction Mechanisms Section: 12.3 Difficulty Level: Easy 24. A) B) C) D) E)

In the reaction of carbonyl compounds with LiAlH4, the effective reducing species is: Li+ Al+3 AlH4AlH3 HAns: E

809

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Medium 25. Select the correct reagent(s) for the following reaction: OH

O CH3CCH 2CH2 CO 2CH3

A) B) C) D) E)

CH3CHCH 2CH2 CH2 OH

LiAlH4/ether; then H3O+ NaBH4; then H3O+ H2 with Pt/C A) and B) A), B) and C) Ans: A

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Medium 26. Select the correct reagent(s) for the following reaction: O

OH

CH3CCH2CH2CO2CH3

A) B) C) D) E)

CH3CHCH2CH2CO2CH3

LiAlH4/ether; then H3O+ NaBH4; then H3O+ H2 with Pt/C B) and C) A), B) and C) Ans: D

810

Topic: Synthetic Strategy, Redox Section: 12.3 Difficulty Level: Medium 27. Which reagent(s) is/are capable of reducing the following ester to an aldehyde ? O O

A) B) C) D) E)

LiAlH4 / ether NaBH4 / H2O Na / C2H5OH H2 / Ni, atmospheric pressure None of the above can be used successfully. Ans: E

Topic: Reactions and Reaction Sequences (Redox) Section: 12.3A Difficulty Level: Medium 28. Predict the product(s) of the following reaction: O

1. LiAlH4 ? H

2. H3O+

CH3

OH

H CH3

H CH3 CH3

H

I

A) B) C) D) E)

H3C

H

II

OH

OH

OH

CH3 H

CH3 H CH3

H

III

A mixture of I and II A mixture of I and III A mixture of II and III A mixture of II and IV A mixture of III and IV Ans: B

811

H3C

H

IV

Topic: Reactions and Reaction Sequences Section: 12.3A Difficulty Level: Medium 29. What product(s) is/are formed in the following reaction? O D2O LiAlD4 ? ether CH3CH 2CH2 COCH2CH 3 A) B) C) D) E)

CH3CH2CH2CH2OD + CH3CH2OD CH3CH2CH2CD2OD + CH3CH2OD CH3CH2CH2CD2OH + CH3CH2OH CH3CH2CH2CHDOD + CH3CH2OD OD CH3CH 2CH2 CDOCH2CH 3

Ans: B Topic: Reactions and Reaction Sequences (Redox) Section: 12.3A Difficulty Level: Medium 30. Predict the product(s) of the following reaction: O

1. LiAlD4 ?

H H

CH3

OH

OH H

CH3

H3C

H

I

II

A) B) C) D) E)

A mixture of I and II A mixture of I and III A mixture of II and III A mixture of II and IV A mixture of III and IV Ans: B

OH

OH

D H

D H

H D

D H

2. H3O+

H

CH3

III

812

H3 C

H

IV

Topic: Reactions and Reaction Sequences (Redox) Section: 12.3B Difficulty Level: Easy 31. What would be the product, A, of the following reaction ? i) NaBD4 A ii) H2O O A) OD

B)

D

OH

C) D

OD

D) OH

E) D O

Ans: B Topic: Synthetic Strategy, Redox Section: 12.3B Difficulty Level: Easy 32. Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CHO into CH3CH2CH=CHCH2CH2CH2OH? A) KMnO4 B) NaBH4 C) Br2 in CCl4 D) H2, Ni E) Two of the above Ans: B

813

Topic: Synthetic Strategy, Redox Section: 12.3B Difficulty Level: Easy 33. Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2C≡CCH2CH2CHO into CH3CH2C≡CCH2CH2CH2OH? A) KMnO4 B) NaBH4 C) Br2 in CCl4 D) H2, Ni E) Two of the above Ans: B Topic: Reactions and Reaction Sequences (Redox) Section: 12.3B Difficulty Level: Medium 34. Predict the product(s) of the following reaction: O

1. NaBH4 H

CH3

OH

OH H

CH3

H3C

H

I

II

A) B) C) D) E)

A mixture of I and II A mixture of I and III A mixture of II and III A mixture of II and IV A mixture of III and IV Ans: B

OH

OH

CH3 H

CH3 H

H CH3

CH3 H

?

2. H3O+

H

CH3

III

814

H3C

H

IV

Topic: Reactions and Reaction Sequences Section: 12.3B Difficulty Level: Hard 35. What would be the major product of the following reaction? O i) NaBH4

ii) ethylene oxide, HA

O

OH

I HO

HO

O

O

O

III

II O

A

O

OH

OH

IV A) B) C) D) E)

V

I II III IV V Ans: A

Topic: Reactions and Reaction Sequences (Redox, SN2) Section: 12.3B and Various Difficulty Level: Hard 36. What would be the major product of the following reaction?

O

i) NaBH4 ii) NaH, Et2O iii) O

S

A

O

OCH2CH3

A) B) C) D) E)

CH3CH2OCH(CH3)CH2CH2CH2CH3 (CH3CH2O)2CHCHOHCH2CH2CH3 (CH3CH2)2CHOHCH2CH2CHOHCH3 CH3OCH(C2H5)CH2CH2CH2CH3 CH3CH2CH(OCH3)CH2CH2CHOHCH3 Ans: A

815

OH

Topic: Redox, Reaction Mechanisms Section: 12.4 Difficulty Level: Easy 37. The reagent PCC in methylene chloride is successful in the selective oxidation of primary alcohols to aldehydes because: A) PCC is a relatively weak oxidizing agent. B) primary alcohols cannot oxidize any further. C) hydration of the intermediate aldehyde is unable to take place in methylene chloride. D) methylene chloride is a reducing agent. E) None of the above Ans: C Topic: Redox, Reaction Mechanisms Section: 12.4 Difficulty Level: Easy 38. A) B) C) D) E)

Fundamentally, 2-methyl-2-pentanol does not undergo oxidation by H2CrO4 because: the intermediate chromate ester is not formed. the oxidant isn't in a sufficiently high oxidation state. the alcohol undergoes dehydration. the intermediate chromate ester cannot lose hydrogen. Actually, this oxidation does occur. Ans: D

Topic: Synthetic Strategy, Redox Section: 12.4 Difficulty Level: Medium 39. Which of the reagents listed below would efficiently accomplish the transformation of 2-methyl-3-cyclopentenol into 2-methyl-3-cyclopentenone? OH

O

? A) B) C) D) E)

KMnO4(aq, alkaline) CrO3/H2SO4 H2, Pt Br2, CCl4 Two of the above Ans: B

816

Topic: Reactions and Reaction Sequences (Chemical Tests) Section: 12.4 Difficulty Level: Medium 40. A) B) C) D) E)

When 1-pentanol is treated with alkaline potassium permanganate, the color changes from orange to blue. the color changes from purple to colorless. the color changes from blue to red. the color changes from orange to green. the color changes from green to orange. Ans: B

Topic: Reactions and Reaction Sequences (Redox) Section: 12.4A Difficulty Level: Easy 41. What is the predominant product from the reaction of 2-hexanol with PCC in CH2Cl2? A) CH3CO2H B) CH3(CH2)3CO2H O C) CH3(CH2)3CCH3

D) CH3(CH2)4CO2H E) A) and B) Ans: C Topic: Synthetic Strategy, Redox Section: 12.4A Difficulty Level: Easy 42. Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO ? A) KMnO4(aq, alkaline) B) CrO3 / H2SO4 C) PCC in CH2Cl2 D) Br2, CCl4 E) Two of the above Ans: C

817

Topic: Reactions and Reaction Sequences (Redox) Section: 12.4B Difficulty Level: Easy 43. What is the predominant product from the reaction of 2-hexanol with KMnO4? A) CH3CO2H B) CH3(CH2)3CO2H O C) CH3(CH2)3CCH3

D) CH3(CH2)4CO2H E) A) and B) Ans: C Topic: Reactions and Reaction Sequences (Redox) Section: 12.4C Difficulty Level: Easy 44. What is the predominant product from the reaction of 2-hexanol with Na2Cr2O7/H+? A) CH3CO2H B) CH3(CH2)3CO2H O C) CH3(CH2)3CCH3

D) CH3(CH2)4CO2H E) A) and B) Ans: C Topic: Reactions and Reaction Sequences (Redox) Section: 12.4C Difficulty Level: Easy 45. What is the predominant product from the reaction of 2-hexanol with H2CrO4? A) CH3CO2H B) CH3(CH2)3CO2H O C) CH3(CH2)3CCH3

D) CH3(CH2)4CO2H E) A) and B) Ans: C

818

Topic: Functional Group Tests Section: 12.4C Difficulty Level: Easy 46. CrO3 in H2SO4/H2O will fail to give a positive test with which of these compounds? A) CH3CH2CH2CH2OH B) CH3CHCH2CH3 OH

C) (CH3)3COH H D) CH3CH2CH2C

O

E) More than one of these Ans: C Topic: Functional Group Tests Section: 12.4E Difficulty Level: Easy 47. A) B) C) D) E)

Which reagent(s) will distinguish between cyclopentanol and cyclopentane? Br2/CCl4 KMnO4 (cold) CrO3/aqueous H2SO4 NaOH (aq) A) and B) Ans: C

Topic: Functional Group Tests Section: 12.4E Difficulty Level: Easy 48. Which reagent(s) will distinguish between 2-methylcyclopentanol and 1methylcyclopentanol? A) Br2/CCl4 B) KMnO4 C) CrO3/aqueous H2SO4 D) NaOH (aq) E) B) and C) Ans: E

819

Topic: Functional Group Tests Section: 12.4E Difficulty Level: Easy 49. Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)3COH and (CH3)2CHCH2OH ? A) NaH B) NaOH/H2O C) Br2 in CCl4 D) Cold conc. H2SO4 E) CrO3 in H2SO4 Ans: E Topic: Functional Group Tests Section: 12.4E Difficulty Level: Medium 50. Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between CH3CH=CHCH3 and CH3CHOHCH2CH3? A) CrO3 in H2SO4 B) KMnO4 C) Br2 in CCl4 D) Two of these E) All of these Ans: D Topic: Functional Group Tests Section: 12.4E Difficulty Level: Medium 51. Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between CH3CH=CHCH2OH and CH3CH2CH2CH2OH ? A) CrO3 in H2SO4 B) Cold conc. H2SO4 C) Br2 in CCl4 D) NaOH/H2O E) NaBH4 Ans: C

820

Topic: Functional Group Tests Section: 12.4E Difficulty Level: Medium 52. Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)2C=CHCH2CH2OH and (CH3)2CHCH2CH2CH2OH ? A) CrO3 in H2SO4 B) Cold conc. H2SO4 C) Br2 in CCl4 D) NaOH/H2O E) NaBH4 Ans: C Topic: Functional Group Tests Section: 12.4E Difficulty Level: Medium 53.

CH3 CHCH

A) B) C) D) E)

2OH. Consider the molecule CH3CHC Which reagent will not give a positive test with this compound? Cold conc. H2SO4 Br2/CCl4 NaOH (aq) CrO3/H2SO4 Dilute KMnO4/H2O Ans: C

Topic: Reactions and Reaction Sequences (Chemical Tests) Section: 12.4E Difficulty Level: Medium 54. A) B) C) D) E)

When 2-pentanol is treated with chromic acid, the color changes from orange to blue. the color changes from purple to colorless. the color changes from blue to red. the color changes from orange to green. the color changes from green to orange. Ans: D

821

Topic: Reactions and Reaction Sequences (Chemical Tests) Section: 12.4E Difficulty Level: Medium 55. A) B) C) D) E)

When 3-methyl-3-pentanol is treated with chromic acid, the color changes from orange to blue. the color changes from purple to colorless. the purple color remains unchanged. the color changes from orange to green. the orange color remains unchanged. Ans: E

Topic: Functional Group Tests Section: 2.16A and 12.4E Difficulty Level: Medium 56. Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-2-ol and 2-methyl-5-hexyn-1-ol? A) CrO3 in H2SO4 B) IR spectroscopy C) Br2 in CCl4 D) A) and B) E) All of the above Ans: D Topic: Functional Group Tests Section: 2.16A and 12.4F Difficulty Level: Medium 57. Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-1-ol and 2-methyl-5-hexyn-1-ol? A) CrO3 in H2SO4 B) Cold conc. H2SO4 C) Br2 in CCl4 D) NaBH4 E) IR spectroscopy Ans: E

Topic: Functional Group Tests

822

Section: 2.16B and 12.4F Difficulty Level: Medium 58. Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between CH3CH2CH=CHCH2CH2CHO and CH3CH2CH=CHCH2CH2CH2OH? A) KMnO4 B) IR spectroscopy C) Br2 in CCl4 D) A) and B) E) All of the above An...