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Chapter Eleven MULTIPLE CHOICE QUESTIONS Topic: Structure and Nomenclature Section: 5.3 and 11.1 Difficulty Level: Hard 1. What is the relationship between alcohols I and II? CH3 OH CH3 HO

I

A) B) C) D) E)

II

They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: C

703

Topic: Structure and Nomenclature Section: 5.3 and 11.1 Difficulty Level: Hard 2. What is the relationship between alcohols I and II? CH3

CH3

OH

A) B) C) D) E)

OH

I II They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: C

Topic: Structure and Nomenclature Section: 5.3 and 11.1 Difficulty Level: Hard 3. What is the relationship between alcohols I and II? OH

CH3

OH

A) B) C) D) E)

CH3

I II They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: C

704

Topic: Structure and Nomenclature Section: 5.3 and 11.1 Difficulty Level: Hard

4. What is the relationship between alcohols I and II? CH3

H CH3 OH

H

OH

H

A) B) C) D) E)

H

I II They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: C

Topic: Structure and Nomenclature Section: 5.12 and 11.1 Difficulty Level: Hard

5. What is the relationship between alcohols I and II? H

H CH3 OH H

A) B) C) D) E)

H

CH3

OH

I II They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: D

705

Topic: Structure and Nomenclature Section: 5.12 and 11.1 Difficulty Level: Hard 6. What is the relationship between alcohols I and II? CH3

CH3 HO

HO

I

A) B) C) D) E)

II

They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: D

Topic: Structure and Nomenclature Section: 5.12 and 11.1 Difficulty Level: Hard 7. What is the relationship between alcohols I and II? CH3

CH3

OH

I

A) B) C) D) E)

OH

II

They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: D

706

Topic: Nomenclature Section: 11.1A Difficulty Level: Easy 8. What is the correct IUPAC name for the following compound? CH3 CH3CHOHCHCHCH(CH3)2 A) B) C) D) E)

CH3 4-isopropyl-3,4-dimethyl-2-butanol 2,3,4-trimethyl-4-pentanol 1,1,2,3-tetramethyl-4-pentanol 3,4,5-trimethyl-2-hexanol 3,4,5,5-tetramethyl-2-pentanol Ans: D

Topic: Nomenclature Section: 11.1A Difficulty Level: Easy 9. A) B) C) D) E)

A correct IUPAC name for isobutyl alcohol is: 2-Methyl-1-propanol 2-Methyl-1-butanol 1-Methyl-1-propanol 1,1-Dimethyl-1-ethanol 3-Methyl-1-propanol Ans: A

Topic: Nomenclature Section: 11.1A Difficulty Level: Easy CH2CH3

10.

CH3CH2COH

A) B) C) D) E)

The IUPAC name of compound 1,1,1-Triethylmethanol 1,1-Diethyl-1-propanol 2-Ethyl-3-pentanol 3-Ethyl-3-pentanol tert-Heptanol Ans: D

CH2CH3 is:

707

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium

11. What is the correct IUPAC name for the following compound? CH3 CH3CH2C=CCH2CH3 A) B) C) D) E)

CH2CH2OH 3-methyl-4-ethyl-3-hexen-6-ol 4-ethyl-3-methyl-3,6-hexenol 3-ethyl-4-methyl-3-hexen-1-ol 3-methyl-4-(2-hydroxyethyl)-3-hexene 3-(2-hydroxyethyl)- 3-methyl-3-hexene Ans: C

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium 12. What is a correct IUPAC name for the following compound?

HO

A) B) C) D) E)

OH

1,2-butanediol isopropanol 1-propanol 1,2-propanediol Ethylene glycol Ans: D

708

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium 13. What is a correct IUPAC name for the following compound? HO

A) B) C) D) E)

OH

1,2-butanediol isopropanol 1-proanol Propylene glycol 1,2-ethanediol Ans: E

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium

14. A) B) C) D) E)

The correct IUPAC name for tert-butyl alcohol is: 1-Butanol 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Butanol 1,1-Dimethyl-1-ethanol Ans: C

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium 15. A) B) C) D) E)

2,2-Dimethyl-1-propanol has the common name: Isoamyl alcohol Isopentyl alcohol tert-Pentyl alcohol Neopentyl alcohol 2-Methylisobutyl alcohol Ans: D

709

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium 16. A) B) C) D) E)

Which of these, though often used, is an incorrect common name for CH3CHOHCH3? Isopropyl alcohol sec-Propyl alcohol 2-Propanol Isopropanol More than one of these. Ans: D

Topic: Nomenclature Section: 11.1A Difficulty Level: Medium 17. A) B) C) D) E)

Which of these, though often used, is an incorrect common name for (CH3)3COH? tert-Butyl alcohol tert-Butanol 2-Methyl-2-propanol More than one is incorrect. Each is a correct name. Ans: B

Topic: Isomerism, Stereoisomers Section: 11.1A Difficulty Level: Medium 18. A) B) C) D) E)

Which of the following can be described as “optically active, primary alcohol”? CH3CH2CH2CH2CH2OH (CH3)2CHCH2CH2OH CH3CH2CH(CH3)CH2OH (CH3)2CHCHOHCH3 Two of the above Ans: C

710

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard OH

19.

A) B) C) D) E)

The correct IUPAC substitutive name for 4-Penten-2-methyl-2-ol 4-Methyl-1-penten-2-ol 2-Methyl-4-penten-2-ol 4-Methyl-1-penten-4-ol 4-Hydroxy-4-methyl-1-pentene Ans: C

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 20.

OH OH

A) B) C) D) E)

is properly named: cis-1,2-Cyclopentanediol meso-1,2-Cyclopentanediol (1R,2R)-1,2-Cyclopentanediol (1R,2S)-1,2-Cyclopentanediol (1S,2S)-1,2-Cyclopentanediol Ans: C

711

is:

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 21.

OH

OH

A) B) C) D) E)

is properly named: 1,2-Cyclopentanediol 1,5-Cyclopentanediol (1R,2R)-1,2-Cyclopentanediol (1R,2S)-1,2-Cyclopentanediol (1S,2S)-1,2-Cyclopentanediol Ans: D

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 22.

OH OH

A) B) C) D) E)

is properly named: cis-1,2-Cyclohexanediol meso-1,2-Cyclohexanediol (1R,2R)-1,2-Cyclohexanediol (1R,2S)-1,2-Cyclohexanediol (1S,2S)-1,2-Cyclohexanediol Ans: C

712

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 23.

OH OH

A) B) C) D) E)

is properly named: 1,2-Cyclohexanediol 1,6-Cyclohexanediol (1R,2R)-1,2-Cyclohexanediol (1R,2S)-1,2-Cyclohexanediol (1S,2S)-1,2-Cyclohexanediol Ans: D

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 24.

OH

OH

A) B) C) D) E)

is properly named: 1,3-Cyclopentanediol 1,4-Cyclopentanediol (1R,3R)-1,3-Cyclopentanediol (1R,3S)-1,3-Cyclopentanediol (1S,3S)-1,3-Cyclopentanediol Ans: C

713

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 25.

HO

OH

A) B) C) D) E)

is properly named: 1,4-Cycloheptanediol 1,5-Cycloheptanediol (1R,4R)-1,4-Cycloheptanediol (1R,4S)-1,4-Cycloheptanediol (1S,4S)-1,4-Cycloheptanediol Ans: D

Topic: Nomenclature Section: 11.1A Difficulty Level: Hard 26. A correct name for the following Fischer projection formula is: OH H3C

C

C

CH3 H

A) B) C) D) E)

(R)-3-Pentyn-2-ol (S)-3-Pentyn-2-ol (R)-2-Pentyn-4-ol (S)-2-Pentyn-4-ol (S)-2-Hydroxy-3-pentyne Ans: B

714

Topic: Stereoisomerism Section: 11.1B Difficulty Level: Easy 27. What is the relationship between alcohols I and II? CH3

CH3 HO OH

I

A) B) C) D) E)

II

They are: different conformations of the same compound. constitutional isomers. enantiomers. diastereomers. identical. Ans: B

715

Topic: Nomenclature Section: 11.1B Difficulty Level: Medium 28. Select the structure of benzyl methyl ether. I

CH3

II

CH3O

III

CH3 O CH2

IV

V A) B) C) D) E)

O

CH3

CH O CH CH3 CH3 CH3

CH2

O

CH2

CH3

I II III IV V Ans: C

Topic: Nomenclature Section: 11.1B Difficulty Level: Medium 29. A) B) C) D) E)

Which is a correct IUPAC name for CH3CH2OCH2CH2CH2OCH2CH3? 1,4-Dioxane Ethylene glycol diethyl ether 1,3-Diethoxypropane 1,2-Diethoxyethane 1,2-Diethoxymethane Ans: C

716

Topic: Isomerism, Stereoisomers Section: 11.1B Difficulty Level: Medium 30. A) B) C) D) E)

What is the total number of pentyl alcohols, including stereoisomers? 7 8 9 10 11 Ans: E

Topic: Isomerism, Stereoisomers Section: 11.1B Difficulty Level: Medium 31. The number of primary alcohols corresponding to the formula C5H12O, counting stereoisomers separately, is: A) 1 B) 2 C) 3 D) 4 E) 5 Ans: E Topic: Isomerism, Stereoisomers Section: 11.1B Difficulty Level: Medium 32. The number of tertiary alcohols corresponding to the formula C5H12O, counting stereoisomers separately, is: A) 1 B) 2 C) 3 D) 4 E) 5 Ans: A

717

Topic: Isomerism, Stereoisomers Section: 11.1B Difficulty Level: Medium 33. The number of secondary alcohols corresponding to the formula C5H12O, counting stereoisomers separately, is: A) 1 B) 2 C) 3 D) 4 E) 5 Ans: E Topic: Isomerism, Stereoisomers Section: 11.1B Difficulty Level: Medium 34. The total number of ethers corresponding to the formula C5H12O, counting stereoisomers separately, is: A) 4 B) 5 C) 6 D) 7 E) 8 Ans: D Topic: Isomerism, Stereoisomers Section: 11.1B Difficulty Level: Medium 35. The number of optically active pentyl alcohols (C5H11OH), i.e., the total number of individual enantiomers, is: A) 0 B) 2 C) 3 D) 4 E) 6 Ans: E

718

Topic: Nomenclature Section: 11.1B Difficulty Level: Hard 36. What is the most accurate name for the molecule represented by the following Fischer projection formula? H H3CH2C

A) B) C) D) E)

OCH3 CH3

sec-Butyl methyl ether Isobutyl methyl ether tert-Butyl methyl ether (R)-2-Methoxybutane (S)-2-Methoxybutane Ans: E

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy

37. Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight.) A) CH3CH2CH2CH2CH3 B) CH3CH2CH2CH2OH C) CH3CH2CH2OCH3 D) CH3CH2CH2Cl E) CH3CH2OCH2CH3 Ans: B Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 38. A) B) C) D) E)

Which compound would have the highest boiling point? CH3CH2CH2CH3 CH3CH2OCH3 CH3CH2CH2OH (CH3)2CHOH HOCH2CH2OH Ans: E

719

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 39. A) B) C) D) E)

Which compound would have the lowest boiling point? CH3CH2CH2CH3 CH3CH2OCH2CH3 CH3CH2CH2OH (CH3)2CHOH HOCH2CH2OH Ans: A

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 40. A) B) C) D) E)

Which compound would have the highest boiling point? CH3CH2CH2CH3 CH2(OH)CH(OH)CH2OH CH3CH2CH2OH (CH3)2CHOH HOCH2CH2OH Ans: B

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 41. A) B) C) D) E)

Which compound would have the lowest solubility in water? Diethyl ether Methyl propyl ether 1-Butanol 2-Butanol Pentane Ans: E

720

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 42. A) B) C) D) E)

Which compound would have the greatest solubility in water? Diethyl ether Methyl propyl ether 1-Butanol 1,2-Butanediol Pentane Ans: D

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 43. Which compound would have the lowest boiling point? OH

O

I A) B) C) D) E)

II

OH

III

I II III IV V Ans: A

721

CH2OH

IV

OH

V

Topic: Physical Properties, Comparison Section: 11.2 Difficulty Level: Easy 44. Which compound would have the highest boiling point? O

O

O

O

O

OH

I

II

III OH

O O

IV A) B) C) D) E)

OH

V

I II III IV V Ans: E

Topic: Ether Reactivity Section: 11.2 Difficulty Level: Easy 45. Which of the following statements is NOT true of ethers? A) Ethers are generally unreactive molecules toward reagents other than strong acids. B) Ethers generally have lower boiling points than alcohols of a corresponding molecular weight. C) Ethers generally have much lower water solubilities than alcohols with a corresponding molecular weight. D) Ethers can generally be cleaved by heating them with strong acids. E) Ethers form peroxides when allowed to stand in the presence of oxygen. Ans: C

722

Topic: General Section: 11.3A Difficulty Level: Easy 46. A) B) C) D) E)

The major industrial process in use today for the production of methanol is the: hydration of ethyne. distillation of wood. hydrogenation of carbon dioxide. reduction of methanal. catalytic reduction of carbon monoxide. Ans: E

Topic: General Section: 11.3B Difficulty Level: Easy 47. A) B) C) D) E)

Today, most industrial ethanol is made in the U.S. by the: fermentation of grain. hydrolysis of ethyl bromide. hydration of ethylene. reduction of acetaldehyde. hydration of acetylene. Ans: C

Topic: Ether Reaction Rates Section: 11.3D Difficulty Level: Easy 48. Which of these ethers is most resistant to peroxide formation on exposure to atmospheric oxygen? A) CH3OCH2CH3 B) CH3CH2OCH2CH3 C) (CH3)2CHOCH(CH3)2 D) (CH3)2CHOCH2CH3 E) CH3OC(CH3)3 Ans: E

723

Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Easy 49. Which product(s) would you expect to obtain from the following sequence of reactions? CH3

1. BH 3-THF

?

2. H2O2, NaOH CH3 CH3 OH

O OH

+ enantiomer

A) B) C) D) E)

I I II III IV V Ans: C

H3C

CH3

II

CH2OH

OH

+ enantiomer

+ enantiomer

III

IV

724

V

Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Easy 50. Select the structure of the major product formed from the following reaction. CH3

1. Hg(OOCCH3)2 THF, H2O

?

2. NaBH4, NaOH CH3

CH3

CH2OH

HO CH3

OH

CH3 OH

OH

I A) B) C) D) E)

II

III

IV

V

I II III IV V Ans: D

Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Easy 51. Anti-Markovnikov hydration of the carbon-carbon double bond occurs when an alkene reacts with: A) BH3:THF; then H2O2/OHB) BH3:THF; then CH3COOH C) Hg(OAc)2, THF, H2O; then NaBH4, OHD) Hg(OAc)2, THF, CH3OH; then NaBH4, OHE) Hg(OAc)2, THF, H2O; then BH3:THF Ans: A

725

Topic: Reaction Mechanisms Section: 11.4 Difficulty Level: Easy 52. Which statement is true concerning the formation of alcohols by the hydroborationoxidation sequence? A) Overall, the process results in syn addition and anti-Markovnikov orientation. B) Overall, the process results in anti addition and anti-Markovnikov orientation. C) Overall, the process results in syn addition and Markovnikov orientation. D) Overall, the process results in anti addition and Markovnikov orientation. E) The stereochemistry and orientation are unpredictable. Ans: A Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Medium

53. Which would be the best way to carry out the following synthesis? ? CH3CH 2CHCH 3

CH3CH 2CH2CH 2OH

Br

A) B) C) D) E)

(1) HA, heat; (2) H3O+, H2O, heat (1) (CH3)3COK / (CH3)3COH; (2) BH3:THF, then H2O2, OH(1) (CH3)3COK / (CH3)3COH; (2) H3O+, then H2O, heat (1) KOH, C2H5OH; (2) BH3:THF, then H2O2, OH(1) KOH, C2H5OH; (2) HA, heat; (3) H3O+, H2O, heat Ans: B

726

Topic: Alcohol Synthesis, Mechanisms Section: 11.4 Difficulty Level: Medium 54. Select the potential energy diagram that best represents the following reaction: H+

OH

H 2O

A) B) C) D) E)

I II III IV V Ans: D

727

Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Medium 55. Which reaction can accomplish the following transformation in good yield: ?

OH

A) H+/H2O B) oxymercuration/demercuation C) hydroboration/oxidation D) Reaction with NaOH E) None of the above Ans: B Topic: Alcohol Synthesis, Isotope Labeling Section: 11.4 Difficulty Level: Medium 56. The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives, by using BD3 instead of BH3. What product would you expect from the following reaction? CH3

1. (BD3)2

?

2. H2O2/NaOH HO H

D

H CH3

+ enantiomer I

A) B) C) D) E)

H

D

BD2 CH3

+ enantiomer II

D

D CH3

H

+ enantiomer III

I II III IV V Ans: A

728

H

OH CH3

+ enantiomer IV

H D

BD2 CH3

+ enantiomer V

Topic: Alcohol Synthesis, Isotope Labeling Section: 11.4 Difficulty Level: Medium 57. The oxymercuration-demercuration procedure can be successfully employed for synthesis of deuterated derivatives, by using NaBD4 instead of NaBH4 in the second step. What product would you expect from the following reaction?

1. Hg(OAc)2/H2O

?

2. NaBD4, NaOH

OH OH

I

A) B) C) D) E)

II

OH

OH

D

III

D

D

OH

IV

V

I II III IV V Ans: C

Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Medium 58. Which of the following would be a reasonable synthesis of 2-butanol? RCOOH A) 1-Butene 1. BH3-THF B) 1-Butene 2. H2O2, NaOH 1. Hg(OAc)2, THF, H2O C) 1-Butene 2. NaBH4, NaOH 1. Ha(OAc)2/CH3OH D) 1-Butene 2. NaBH4, NaOH E) None of these Ans: C

729

730

Topic: Alcohol Synthesis Section: 11.4 Difficulty Level: Medium 59. Which of the following would be a reasonable synthesis of CH3CH2CH2CH2OH? A) H3O +, heat 1-Butene 1. BH3-THF B) 1-Butene 2. H2O2, NaOH 1. Hg(OAc)2, THF, H2 O C) 1-Butene 2. NaBH4 , NaOH 1. Ha(OAc)2/CH3OH D) 1-Butene 2. NaBH4, NaOH E) None of these Ans: B Topic: Alc...