Organic chemistry 10th edition solomons test bank

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Chapter Seven MULTIPLE CHOICE QUESTIONS

Topic: Nomenclature Section: 4.3, 4.5, 7.2 Difficulty Level: Easy 1. The correct IUPAC name for the following compound is: Br

A) 2-Bromo-4-methylenehexane B) 2-(2-Bromopropyl)-1-butene C) 4-Bromo-2-ethyl-1-pentene D) 2-Bromo-4-ethyl-1-pentene E) 2-Bromo-4-ethyl-4-pentene Ans: C Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 7.2 Difficulty Level: Medium 2. Name the following compound: OCH3

A) (cis)-3-methoxyhex-3-ene B) (Z)-4-methoxyhex-4-ene C) (Z)-3-methoxyhex-3-ene D) (E)-3-methoxyhex-3-ene E) 3-methoxyhex-3-ene Ans: C

386

Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 7.2 Difficulty Level: Medium 3. Name the following compound: HO

A) (E)-4-phenyl-4-methylbut-3-en-1-ol B) (E)-4-phenylpent-3-en-1-ol C) (Z)-4-phenylpent-3-en-1-ol D) (Z)-4-phenyl-4-methylbut-3-en-1-ol E) (E)-4-benzylpent-3-en-1-ol Ans: B Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 7.2 Difficulty Level: Medium 4. Which structure represents (Z)-4-bromohexa-1,3-diene?

A) Br

B) Br

C) Br

D)

Br

E) None of the above Ans: C

387

Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 7.2 Difficulty Level: Medium 5. Which structure represents (E)-1-bromo-2-methylhex-2-ene?

A) Br B) Br

C) Br

Br

D)

E) None of the above Ans: A Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 7.2 Difficulty Level: Medium 6. Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?

A) Cl Cl

Cl

B) C)

Cl

Cl Cl

D)

Cl

Cl

E) None of the above Ans: B

388

Topic: Nomenclature Section: 4.5, 7.2 Difficulty Level: Easy 7. A correct IUPAC name for the following compound is:

A) 3,3,5-trimethyl-2-hexene B) 3-isobutyl-3-isopropyl-2-propene C) 3-isobutyl-4-methyl-2-pentene D) 3-(1-methylethyl)-5-methyl-2-hexene E) None of the above Ans: E

Topic: Nomenclature Section: 4.5, 7.2 Difficulty Level: Easy 8. The correct IUPAC name for the following compound is:

A) 4,5-Dimethyl-3-propyl-2-hexene B) 4,5-Dimethyl-3-propyl-1-hexene C) 3-(2,3-Dimethylpropyl)-1-hexene D) 2,3-Dimethyl-4-isopropyl-5-hexene E) 2,3-Dimethyl-4-propyl-5-hexene Ans: B

389

Topic: Nomenclature Section: 4.5, 7.2 Difficulty Level: Easy 9. Select the structure of 4–ethyl-2,3-dimethyl-2-heptene.

A)

B)

C)

D)

E)

Ans: B

Topic: Nomenclature Section: 4.5, 7.2 Difficulty Level: Medium 10. The correct IUPAC name for the following compound is: Cl

Br

A) (E)-2-Bromo-3-chloro-5-methyl-2-hexene B) (E)-2-Bromo-3-chloro-5-methyl-3-hexene C) (Z)-2-Bromo-3-chloro-5-methyl-3-hexene D) (Z)-2-Bromo-3-chloro-5-methyl-2-hexene E) (E)-2-Methyl-5-bromo-4-chloro-4-hexene Ans: A

390

Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 5.7, 7.2 Difficulty Level: Medium 11. Name the following compound: Br

A) (S,Z)-3-bromo-4-methylhex-2-ene B) (S)-3-bromo-4-methylhex-2-ene C) (S,Z)-4-bromo-3-methylhex-4-ene D) (S,E)-3-bromo-4-methylhex-2-ene E) (R,E)-3-bromo-4-methylhex-2-ene Ans: A Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 5.7, 7.2 Difficulty Level: Medium 12. Name the following compound: Br Br

A) (S,E)-2,4-dibromo-3-methylpent-2-ene B) (R,Z)-2,4-dibromo-3-methylpent-2-ene C) (R,E)-2,4-dibromo-3-methylpent-3-ene D) (S,E)-2,4-dibromo-3-methylpent-3-ene E) (R,E)-2,4-dibromo-3-methylpent-2-ene Ans: E

391

Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 5.7, 7.2 Difficulty Level: Hard 13. Name the following compound:

OH

A) (R,Z)-5-phenyloct-5-en-3-ol B) (R,Z)-5-benzyloct-5-en-3-ol C) (R,E)-5-phenyloct-5-en-3-ol D) (R,E)-5-benzyloct-5-en-3-ol E) (R,E)-5-benzyloct-3-en-6-ol Ans: B Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 5.7, 7.2 Difficulty Level: Hard 14. Which structure represents (R,Z)-5-methylhept-2-ene?

A)

B) C)

D)

E) None of the above Ans: D

392

Topic: Nomenclature; Stereochemistry Section: 4.3, 4.5, 4.6, 5.7, 7.2 Difficulty Level: Medium 15. Name the following compound: Cl

A) (S,E)-3-chlorohex-4-en-1-yne B) (R,E)-3-chlorohex-2-en-5-yne C) (S,E)-3-chlorohex-2-en-5-yne D) (R,E)-3-chlorohex-4-en-1-yne E) (R,E)-3-chloropent-4-en-1-yne Ans: D Topic: Alkene Stability, Heats of Hydrogenation and Combustion Section: 7.3 Difficulty Level: Easy 16. Which molecule would have the lowest heat of hydrogenation?

I

II

III

IV

A) I B) II C) III D) IV E) V Ans: A

393

V

Topic: Alkene Stability, Heats of Hydrogenation and Combustion Section: 7.3 Difficulty Level: Easy 17. Heats of hydrogenation data would be useful in comparing the relative stabilities of which of the following substances?

I II III IV V A) I, II, III B) III, IV C) I, II, V D) Heats of hydrogenation data would not be a useful way to compare relative stabilities of any of the substances.

E) All of the above substances could effectively be compared using heats of hydrogenation data.

Ans: C

Topic: Alkene Stability, Heats of Hydrogenation and Combustion Section: 7.3 Difficulty Level: Easy 18. Which alkene would liberate the most heat per mole when subjected to catalytic hydrogenation?

A) B) C) D) E) Ans: A

394

Topic: Alkene Stability, Heats of Hydrogenation and Combustion Section: 7.3 Difficulty Level: Easy 19. Which alkene is most stable?

I

II

III

IV

V

A) I B) II C) III D) IV E) V Ans: A Topic: Alkene Stability, Heats of Hydrogenation and Combustion Section: 7.3 Difficulty Level: Medium 20. Concerning the relative stabilities of alkenes, which is a false statement?

A) Unless hydrogenation of the alkenes gives the same alkane, heats of hydrogenation cannot be used to measure their relative stabilities.

B) In general, the greater the number of alkyl groups attached to the carbon atoms of the double bond, the greater the stability of the alkene.

C) The greater the quantity of heat liberated on combustion or hydrogenation of an alkene, the greater its energy content.

D) trans-Cycloalkenes are always more stable than the cis-isomers.

E) Heats of combustion can be used to measure the relative stabilities of isomeric alkenes, even though their hydrogenation products are not identical.

Ans: D

395

Topic: Alkene Synthesis, Reaction Mechanisms Section: 7.6 Difficulty Level: Easy 21. Which product (or products) would be formed in appreciable amount(s) when trans-1bromo-2-methylcyclohexane undergoes dehydrohalogenation upon treatment with sodium ethoxide in ethanol?

I

II

III

IV

A) I B) II C) III D) IV E) More than one of these Ans: B Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 22. Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use?

A) KOH/H2O B) KOH/CH3OH C) CH3ONa/CH3OH D) CH3CH2ONa/CH3CH2OH E) (CH3)3COK/(CH3)3COH Ans: E

396

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 23. What is the major product for the following reaction?

EtOH, EtONa OTs

heat

A) CH3CH2(CH3)C=CHCH3 B) CH3CH2(CH3)CHCH=CH2 C) CH3CH2(CH3)CHCH(OCH2CH3)CH3 D) None of the above E) No reaction Ans: A Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 24. What is the major product for the following reaction? t-BuOH, t-BuOK Cl

A) Ot-Bu

B)

C) D) E) Ans: E

397

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 25. What is the major product for the following reaction?

I

t-BuOH, t-BuOK

A)

B)

C)

D)

E) None of the above Ans: D

398

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 26. What is the major product for the following reaction?

EtONa, EtOH I

heat

A)

B)

C)

D)

E) None of the above Ans: A

399

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 27. What is the major product for the following reaction?

Cl EtOH, EtONa heat

A)

B)

C)

D)

E)

Ans: A

400

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Easy 28. What is the major product for the following reaction?

Br

t-BuOK, t-BuOH

A)

B)

C)

D)

E)

Ans: E

401

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Medium 29. What is the major product for the following reaction?

EtONa, EtOH Br

heat

A)

B)

C)

D)

E) More than one of the above Ans: C

402

Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms Section: 7.6 Difficulty Level: Medium 30. Dehydrohalogenation of tert-pentyl bromide will produce 2-methyl-1-butene as the chief product when: A) CH3COONa is employed as the base.

B) KOH/C2H5OH is employed as the base.

C) CH3CH2ONa/CH3CH2OH is employed as the base.

D) (CH3)3COK/(CH3)3COH is employed as the base.

E) any base is used, as long as the temperature is sufficiently high.

Ans: D Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Hard 31. What is the major product for the following reaction?

EtOH, EtONa Br

heat

A) OEt

B)

C) D) E) Ans: C

403

Topic: Alkene Synthesis Section: 7.6 Difficulty Level: Hard 32. What is the major product for the following reaction?

EtOH, EtONa Cl

heat

A) OEt

B)

C) D) E) Ans: B

404

Topic: Alkene Synthesis Section: 6.5, 7.6 Difficulty Level: Medium 33. What is the major product for the following reaction?

1. NaI, acetone OTs

2. t-BuOH, t-BuOK

A) B)

C) D) E) Ans: C

405

Topic: Alkene Synthesis Section: 6.5, 7.6 Difficulty Level: Hard 34. What is the major product for the following reaction?

1. NaI, acetone Cl

2. t-BuOH, t-BuOK

A) B)

C) D) E) Ans: D

406

Topic: Alkene Synthesis Section: 6.5, 7.6 Difficulty Level: Hard 35. What is the major product for the following reaction?

1. NaI, acetone Cl

2. NaOH, EtOH, heat

A) B)

C) D) E) Ans: C

407

Topic: Alkene Synthesis Section: 6.5, 7.6 Difficulty Level: Hard 36. What is the major product for the following reaction?

1. NaI, acetone Br

2. EtONa, EtOH, heat

A) B)

C) D) E) Ans: B

408

Topic: Alkene Synthesis, Reaction Mechanisms Section: 6.5, 6.16, 7.6 Difficulty Level: Medium 37. Which compound listed below would you expect to be the major product when 2bromo-2-methylbutane is refluxed with KOH/ethanol?

A) OH

B) O

C) D) E) Ans: D Topic: Alkene Synthesis Section: 7.6B Difficulty Level: Easy 38. Zaitsev's rule states that: A) In electrophilic addition of an unsymmetrical reagent to an unsymmetrical alkene, the more positive portion of the reagent will become attached to the carbon of the double bond bearing the greater number of hydrogen atoms.

B) An equatorial substituent in cyclohexane results in a more stable conformation than if that substituent were axial.

C) E2 reactions occur only if the -hydrogen and leaving group can assume an antiperiplanar arrangement.

D) When a reaction forms an alkene, and several possibilities exist, the more (or most) stable isomer is the one which predominates.

E) The order of reactivity of alcohols in dehydration reactions is 3º > 2º > 1º.

Ans: D

409

Topic: Alkene Synthesis Section: 7.6C Difficulty Level: Easy 39. Regarding the use of potassium tert-butoxide as a base in E2 reactions, it is incorrect to state that: A) this base is more effective than ethoxide ion, because it (KO-t-Bu) is the more basic of the two.

B) it tends to give the anti-Zaitsev, i.e., Hofmann, product.

C) it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol.

D) it favors E2 reactions over competing SN2 reactions.

E) it will form, predominantly, the more stable alkene.

Ans: E Topic: Alkene Synthesis, Reaction Mechanisms Section: 7.6C Difficulty Level: Easy 40. What is the major product of the reaction, (CH3)3COK ?

(CH3)3COH Br

heat

A) (CH3)2C=C(CH3)2 B) (CH3)3C–CH=CH2 C) (CH3)2C=CHCH3 D) (CH3)2C=CHCH2CH3 E) None of these Ans: B

410

Topic: Alkene Synthesis, Reaction Mechanisms Section: 7.6C Difficulty Level: Easy 41. Which compound would be the major product?

Br (CH3)3COK ?

(CH3)3COH heat O

A)

B) C) OH

D) E) Ans: E

411

Topic: Carbocation Stability, Rearrangement Section: 7.7 Difficulty Level: Easy 42. Which statement(s) is/are true of acid-catalyzed alcohol dehydrations?

A) Protonation of the alcohol is a fast step.

B) Formation of a carbocation from the protonated alcohol is a slow step.

C) Rearrangements of less stable carbocations to more stable carbocations are common.

D) Loss of a proton by the carbocation is a fast step.

E) All of the above Ans: E Topic: Alkene Synthesis, Reaction Mechanisms Section: 7.7 Difficulty Level: Easy 43. Which product(s) would be produced by acid-catalyzed dehydration of 2-methyl-2pentanol?

A) B) and

C)

and

D) E) O

Ans: B

412

Topic: Alkene Synthesis; Alcohol Dehydration Section: 7.7 Difficulty Level: Easy 44. Which one of the following alcohols would dehydrate most rapidly when treated with sulfuric acid?

OH

OH

I

II

OH

III OH

OH

IV

V

A) I B) II C) III D) IV E) V Ans: B

413

Topic: Alkene Synthesis; Alcohol Dehydration Section: 7.7 Difficulty Level: Easy 45. Which mechanistic step in the acid-catalyzed dehydration of 3,3-dimethyl-2-butanol is the rate determining step?

A) Step 1: +

H3O+

OH

+

H2O

OH2

B) Step 2: +

H2O

OH2

C) Step 3:

D) Step 4a:

+

H2O

+

H3O+

+

H2O

+

H 3O

E) Step 4b:

Ans: B

414

+

Topic: Alkene Synthesis; Alcohol Dehydration Section: 7.7 Difficulty Level: Easy 46. Which alcohol would be most easily dehydrated?

CH3 A) CH3CH2CCH2CH3 OH CH3

B)

CH3CH2CHCHCH3 OH CH3

C)

CH3CH2CHCH2CH2OH CH3 D) HOCH2CHCH2CH2CH3 CH2OH E) CH3CH2CHCH2CH3 Ans: A

Topic: Alkene Synthesis; Alcohol Dehydration Section: 7.7 Difficulty Level: Easy 47. Which alcohol would be most easily dehydrated?

OH

OH

I

II

OH

III OH

OH

IV

V

A) I B) II C) III D) IV E) V Ans: B

415

Topic: Carbocation Stability Section: 7.7 Difficulty Level: Medium 48. Which alcohol would initially produce the most stable carbocation when treated with concentrated H2SO4?

A) OH B)

OH

C) OH

D) HO

E) HO

Ans: A Topic: Carbocation Stability, Rearrangement Section: 6.10, 6.17, 7.7 Difficulty Level: Hard 49. Carbocations are frequent intermediates in acidic reactions of alkenes, alcohols, etc.

What do carbocations usually do? They may: A) rearrange to a more stable carbocation.

B) lose a proton to form an alkene.

C) combine with a nucleophile.

D) react with an alkene to form a larger carbocation.

E) do all of the above.

Ans: E

416

Topic: Carbocation Stability, Rearrangement Section: 6.11B, 7.7B Difficulty Level: Easy 50. Which of the following carbocations would NOT be likely to undergo rearrangement?

A) CH3CHCHCH3 CH3 CH3 B)

CH3CHCCH3 CH3 C)

CH3 CH3CCH2CH3

D)

CH3

CH3CHCH2 CH3 E)

CH3CCHCH2CH3 CH3 Ans: C Topic: Carbocation Stability, Rearrangement Section: 7.8 Difficulty Level: Hard 51. Neopentyl alcohol, (CH3)3CCH2OH, cannot be dehydrated to an alkene without rearrangement. What is the chief product of dehydration?

I

II

IV

III

V

A) I B) II C) III D) IV E) V Ans: B

417

Topic: Carbocation Stability, Rearrangement Section: 5.12, 6.10, 6.17, 7.8 Difficulty Level: Medium 52. What is the major product of the reaction between methanol and (2R,3S)-2-bromo-3methylpentane at room temperature?

A) B)

OCH3

C) D) H3CO

E) Both A) and C) Ans: D Topic: Carbocation Stability, Rearrangement Section: 6.10, 6.17, 7.8 Difficulty Level: Easy 53. Rearrangements are likely to occur in which of the following reaction types?

A) SN1 reactions B) SN2 reactions C) E1 reactions D) E2 reactions E) Both SN1 and E1 reactions Ans: E

418

Topic: Carbocation Stability, Rearrangement Section: 6.10, 6.17, 7.8 Difficulty Level: Easy 54. What is the major product of the reaction of the following reaction?

I

ethanol, 20 oC

A)

B)

CH3CH2O

OCH2CH3

C)

D)

E) More than one of the above Ans: A

419

Topic: Alkene Synthesis Section: 6.10, 6.17, 7.8 Difficulty Level: Easy 55. What is the major product for the following reaction?

Br

EtOH, heat

A)

B)

C)

D)

E) More than one of the above Ans: E

420

Topic: Alkene Synthesis Section: 6.10, 6.17, 7.8 Difficulty Level: Medium 56. What is the major product for the following reaction?

I

EtOH, heat

A)

B)

C)

D)

E) None of the above Ans: C

421

Topic: Alkene Synthesis Section: 6.10, 6.17, 7.8 Difficulty Level: Medium 57. What is the major product for the following reaction?

Cl

EtOH, heat

A)

B)

C)

D)

E)

Ans: D

422

Topic: Carbocation Stability, Rearrangement Section: 6.10, 6.17, 7.8 Difficulty Level: Hard 58. What is the major product of the reaction of the following reaction?

Cl

EtOH, heat

A) B) OEt

C)

D)

E)

Ans: D

423

Topic: Carbocation Stability, Rearrangement Section: 6.10, 6.17, 7.8 Difficulty Level: Hard 59. What is the major product of the reaction of the following reaction?

EtOH, heat OTs

A)

B)

C)

OEt

D)

E) None of the above Ans: A

424

Topic: Carbocation Stability, Rearrangement Section: 6.10, 6.17, 7.8 Difficulty Level: Hard 60. What is the major product of the reaction of the following reaction?

CH3OH, heat Cl

A) H3CO

B)

C)

D)

E)

Ans: E

425

Topic: Carbocation Stability, Rearrangement Section: 4.16, 6.10, 6.17, 7.3, 7.8 Difficulty Level: Medium 61. What is the major product of the reaction of the following reaction sequence?

Br

1. H2, Ni 2. EtOH, heat

A) B) C)

D)

OEt

E) A mixture of A) and B) Ans: C

426

Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements Section: 7.7, 7.8 Difficulty Level: Medium 62. Which alkene would you expect to be the major product of the following dehydration?

H2SO4 ?

heat OH

I

III

II

IV

V

A) I B) II C) III D) IV E) V Ans: C

427

Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements Section: 7.7, 7.8 Difficulty Level: Hard 63. What will be the major product of the following reaction?

85% H3PO4 ? heat OH

A)

B)

C) D)

O

E) Ans: A

428

Topic: Alkene Synthesis, Nomenclature Section: 7.6C, 7.7, 7.10 Difficulty Level: Medium 64. Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable percentage yield (i.e., greater than 50%)?

A) H2SO4

heat

OH

B)

(CH3)3COK, (CH3)3COH heat

Br

C)

i) 3 NaNH2, mineral oil, heat Br Br

ii) H3O+

D) All of these E) Answers B) and C) only Ans: B Topic: Alkyne Synthesis Section: 7.11 Difficulty Level: Easy 65. Which reaction would yield 2-butyne?

A) CH3CC:− Na+ + CH3Br ⎯⎯⎯⎯→ B) CH3CH2Br + HCC:− Na+ ⎯⎯⎯⎯→ C) CH3:− Na+ + HCCCH3 ⎯⎯⎯⎯→ D) More than one of these E) None of these Ans: A

429