Test Bank Chapter 20 Carboxylic Acids And Their Derivatives

Organic Chemistry, 4e (Klein)

Chapter 20 Carboxylic Acids and Their Derivatives

1) What is the IUPAC name for the compound shown?

A) 2-methylpentanoic acid

B) 3-methylpentanoic acid

C) 2-methylhexanoic acid

D) 3-methylhexanoic acid

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

2) What is the common name for the compound shown?

A) 3-fluorobutanoic acid

B) 2-fluorobutanoic acid

C) β-fluorobutyric acid

D) α-fluorobutyric acid

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

3) What is the IUPAC name for the compound shown?

A) 3-fluorobutanoic acid

B) 2-fluorobutanoic acid

C) β-fluorobutyric acid

D) α-fluorobutyric acid

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

4) What is the IUPAC name for the compound shown?

A) 2,4-dimethylheptanedioic acid

B) 3,5-dimethylheptanedioic acid

C) 2,4-dimethylpentanedioic acid

D) 3,5-dimethylpentanedioic acid

E) 2,4-dimethylheptanoyl acid

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

5) What is the correct structure for trichloroacetic acid?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

6) What is the correct structure for succinic acid?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

7) What is the IUPAC name for the compound shown?

A) (Z)-5-ethyl-3-methyl-3-heptenoic acid

B) (E)-2-ethyl-5-methyl-4-hepten-7-oic acid

C) (Z)-2-ethyl-5-methyl-4-hepten7-oic acid

D) (E)-5-ethyl-3-methyl-3-heptenoic acid

E) (Z)-5-ethyl-3-methyl-3-heptanoic acid

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

8) What is the IUPAC name for the compound shown?

A) 1-ethylcyclohexane-3-carboxylic acid

B) (2-ethyl)-1-cyclohexylmethanecarboxylic acid

C) 1-(2-ethyl)-cyclohexylmethanecarboxylic acid

D) 3-ethylcyclohexanoic acid

E) 3-ethylcyclohexanecarboxylic acid

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

9) What is the structure of 5-chloro-3-isopropyloctanoic acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

10) What is the structure of (3S,4S)-3-hydroxy-4-phenylnonanoic acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

11) What is the IUPAC name for the compound shown?

A) 3-t-butyl-5-isobutylnonanedioic acid

B) 3-t-butyl-5-isobutyl-1,9-nonanoic acid

C) 3-t-butyl-5-isobutylnonanoic acid

D) 5-butyl-3-isobutylnonanedioic acid

E) 3,5-butyl-nonanedioic acid

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

12) What is the IUPAC name for the compound shown?

A) (3-isobutyl)-benzene-methanoic acid

B) 3-isobutylbenzene methanoic acid

C) Isobutylbenzenzne-3-methanoic acid

D) 3-isobutylbenzoic acid

E) 3-isopropylbenzoic acid

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

13) Methanoic acid is commonly known as ________.

A) formic acid

B) acetic acid

C) malonic acid

D) glutaric acid

E) oxalic acid

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

14) Ethanoic acid is commonly known as ________.

A) formic acid

B) acetic acid

C) malonic acid

D) glutaric acid

E) oxalic acid

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

15) What is the IUPAC name for oxalic acid?

A) ethanedioic acid

B) propanedioic acid

C) butanedioic acid

D) pentanedioic acid

E) benzoic acid

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

16) What is the IUPAC name for malonic acid?

A) ethanedioic acid

B) propanedioic acid

C) butanedioic acid

D) pentanedioic acid

E) benzoic acid

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

17) What is the IUPAC name for glutaric acid?

A) ethanedioic acid

B) propanedioic acid

C) butanedioic acid

D) pentanedioic acid

E) benzoic acid

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

18) Which one of the compounds shown has the highest boiling point?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

19) Which one of the compounds shown has the highest boiling point?

A) butanoic acid

B) 1-butanol

C) 2-butanone

D) methoxyethane

E) butanal

Diff: 1

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

20) Which of the compounds shown is the strongest acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

21) Which of the compounds shown is the weakest acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

22) Which one of the compounds shown is the strongest acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

23) Which one of the choices is the strongest acid?

A) benzoic acid

B) 4-nitrobenzoic acid

C) 4-ethylbenzoic acid

D) 4-chlorobenzoic acid

E) 4-hydroxybenzoic acid

Diff: 1

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

24) Which one of the choices is the weakest acid?

A) benzoic acid

B) 4-nitrobenzoic acid

C) 4-ethylbenzoic acid

D) 4-chlorobenzoic acid

E) 4-hydroxybenzoic acid

Diff: 1

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

25) Rank the acids shown in decreasing (strongest to weakest) order of acidity.

A) V > III > I > II > IV

B) II > I > III > V > IV

C) IV > III > I > II > V

D) IV > V > III > I > II

E) V > I > III > II > IV

Diff: 2

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

26) Rank the acids shown in decreasing (strongest to weakest) order of acidity.

A) IV > V > III > I > II

B) II > IV > III > I

C) IV > III > I > II > V

D) V > I > III > II > IV

E) V > III > I > II > IV

Diff: 2

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

27) Which one of the choices is the strongest acid?

A) 2,2-dichlorobutanoic acid

B) 2,3-dichlorobutanoic acid

C) 3,3-dichlorobutanoic acid

D) 3,4-dichlorobutanoic acid

E) 4,4-dichlorobutanoic acid

Diff: 3

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

28) Which one of the choices is the strongest acid?

A) 2,3-dimethylheptanoic acid

B) 3,3-dichlorohexanoic acid

C) 4-bromo-3-iodohexanoic acid

D) 4-bromo-3-chloroheptanoic acid

E) 4-bromo-2-fluorohexanoic acid

Diff: 3

Learning Objective: 20.3 Discuss the structure and acidity of carboxylic acids, including the effect of a substituent on acidity

29) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

30) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

31) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

32) Which of the reagent(s) shown can be used to carry out the given conversion?

A) PCC/CH2Cl2

B) CO2 followed by H3O+

C) mCPBA

D) Na2Cr2O7/H2SO4/H2O

E) both A and D

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

33) Provide the reagents necessary to carry out the conversion shown.

A) 1. H2O; 2. KMnO4

B) 1. O3; 2. DMS; 3. Na2Cr2O7/H2SO4/H2O

C) 1. NaOH, Br2; 2. DMS; 3. H2O/heat

D) 1. O3; 2. DMS; 3. KMnO4

E) 1. DMS; 2. H2O2/heat

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

34) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

35) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

36) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

37) What is the predicted product of the reaction shown?

A) (CH3)2CHCH2COOH

B) (CH3)2CHCH2CH2COOH

C) (CH3)2CHCH2CN

D) (CH3)2CHCH2CH2CN

E) (CH3)2CHCH2OH

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

38) Provide the reagents necessary to carry out the conversion shown.

A) 1. Mg/ether

2. CO2

3. H3O+

B) 1. NaOH

2. KMnO4/NaOH/H2O

3. H3O+

C) 1. NaCN

2. H3O+, heat

D) A and C

E) all of these

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

39) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

40) What reagents are necessary to carry out the conversion shown?

A) 1. ; 2. Mg/ether; 3. KMnO4

B) 1. ; 2 H3O+; 3. KMnO4

C) 1. Mg/ether; 2. CH3CH2CH2Br; 3. H3O+; 4. KMnO4

D) KMnO4/H2O/heat

E) 1. Mg/ether; 2. ; 3. H3O+; 4. Na2Cr2O7/H2SO4/H2O

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

41) What reagents are needed to carry out the conversion shown?

A) 1. Cl2/heat; 2. MgBr; 3. Mg/ether; 4 KMnO4

B) 1. Cl2/FeCl3; 2. Na2Cr2O7/H2SO4/H2O

C) 1. LiAlH4; 2. H2O; 3. HCl

D) 1. Mg/ether; 2. CO2; 3. H3O+

E) 1. Mg/ether; 2. CH3CH2CH2Cl; 3. H3O+; 4. KMnO4

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

42) What reagents are needed to carry out the conversion shown?

A) 1. Br2/heat; 2. MgBr; 3. Mg/ether; 4 KMnO4

B) 1. Br2/FeBr3; 2. Na2Cr2O7/H2SO4/H2O

C) 1. LiAlH4; 2. H2O; 3. HCl

D) 1. Mg/ether; 2. CO2; 3. H3O+

E) 1. Mg/ether; 2. CH3CH2CH2Cl; 3. H3O+; 4. KMnO4

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

43) What is the predicted product of the reaction shown?

A) 3-methyl-2-pentanone

B) 3-methyl -1-propanol

C) 2-methyl-1-butanol

D) 3-methyl-2-pentanol

E) none of these

Diff: 2

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

44) What reagents are necessary to carry out the conversion shown?

A) 1. LiAlH4

2. H2O

B) NaBH4/CH3OH

C) LiAl[OC(CH3)3]H

D) BH3·THF

E) C and D

Diff: 3

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

45) What reagents are necessary to carry out the conversion shown?

A) 1. LiAlH4

2. H2O

B) NaBH4/CH3OH

C) LiAl[OC(CH3)3]H

D) BH3·THF

E) C and D

Diff: 3

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

46) What reagents are necessary to carry out the conversion shown?

A) 1. LiAlH4; 2. H3O+

B) NaBH4/CH3OH

C) LiAl[OC(CH3)3]H

D) BH3·THF

E) C and D

Diff: 3

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

47) What reagents are necessary to carry out the conversion shown?

A) 1. LiAlH4; 2. H3O+

B) 1. Mg/ether; 2. H2C=O; 3. H2O

C) 1. Mg/ether; 2. CO2; 3. H3O+; 4. LiAlH4; 5. H2O

D) A and B

E) B and C

Diff: 3

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

48) What reagents are necessary to carry out the conversion shown?

A) 1. PBr3; 2. Mg/ether; 3. H2C=O; 4. H2O

B) 1. PBr3; 2. Mg/ether; 3. CH3CH2COOH; 4. H3O+; 5. LiAlH4; 6. H2O

C) 1. PBr3; 2. Mg/ether; 3. CO2; 4. H3O+; 5. LiAlH4; 6. H2O

D) A and B

E) A and C

Diff: 3

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

49) What is the predicted product of the reaction sequence shown?

A) 2,2-dimethylpropanoic acid

B) 3,3-dimethyl-2-butanone

C) 2,2-dimethyl-1-propanol

D) 2,2-dimethylbutanoic acid

E) 2,2-dimethylethanoic acid

Diff: 3

Learning Objective: 20.5 Describe how carboxylic acids can be converted to alcohols

50) What is the IUPAC name for the compound shown?

A) α-methylbutyryl chloride

B) β-methylbutyryl chloride

C) γ-methylbutyryl chloride

D) 2-methylbutanoyl chloride

E) 3-methylbutanoyl chloride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

51) What is the common name for the compound shown?

A) α-methylbutyryl chloride

B) β-methylbutyryl chloride

C) γ-methylbutyryl chloride

D) 2-methylbutanoyl chloride

E) 3-methylbutanoyl chloride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

52) What is the common name for the compound shown?

A) α-bromoacetyl bromide

B) β-bromoacetyl bromide

C) 1-bromoethanoyl bromide

D) 2-bromoethanoyl bromide

E) 1,2-dibromoacetic acid

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

53) What is the IUPAC name for the compound shown?

A) bromoacetyl bromide

B) β-bromoacetyl bromide

C) 1-bromoethanoyl bromide

D) bromoethanoyl bromide

E) 1,2-dibromoacetic acid

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

54) What is the IUPAC name for the compound shown?

A) γ-methylvaleryl chloride

B) 2-methylpentanoyl chloride

C) 3-methylhexanoyl chloride

D) 3-methylpentanoyl chloride

E) 2-methylhexanoyl chloride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

55) What is the IUPAC name for the compound shown?

A) α-bromobutyryl chloride

B) β-bromobutyryl chloride

C) 1-bromobutanoyl chloride

D) 2-bromobutanoyl chloride

E) 2-bromopropanoyl chloride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

56) What is the common name for the compound shown?

A) α-bromobutyryl chloride

B) β-bromobutyryl chloride

C) 1-bromobutanoyl chloride

D) 2-bromobutanoyl chloride

E) 2-bromopropanoyl chloride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

57) What is the IUPAC name for the compound shown?

A) 3-ethyl-2,4-dimethylpentanoyl chloride

B) 4-ethyl-3,5-dimethylpentanoyl chloride

C) 3-ethyl-2,4-dimethylhexanoyl chloride

D) 4-ethyl-3,5-dimethylhexanoyl chloride

E) 3,4,5-trimethylhexanoyl chloride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

58) What is the structure of 4-ethylbenzoyl chloride?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

59) What is the structure for cyclopentanecarbonyl chloride?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

60) Provide the structure for benzoyl chloride.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

61) What is the IUPAC name for the compound shown?

A) methanoic anhydride

B) ethanoic anhydride

C) acetic anhydride

D) formic anhydride

E) propanoic anhydride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

62) What is the common name for the compound shown?

A) methanoic anhydride

B) ethanoic anhydride

C) acetic anhydride

D) formic anhydride

E) propanoic anhydride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

63) What is the IUPAC name for the compound shown?

A) propanoic anhydride

B) butanoic anhydride

C) propionic anhydride

D) pentanoic anhydride

E) butyric anhydride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

64) What is the common name for the compound shown?

A) propanoic anhydride

B) butanoic anhydride

C) propionic anhydride

D) pentanoic anhydride

E) butyric anhydride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

65) What is the IUPAC name for the compound shown?

A) methanoic propanoic anhydride

B) formic propionic anhydride

C) ethanoic propionic anhydride

D) acetic butyric anhydride

E) butanoic ethanoic anhydride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

66) What is the common name for the compound shown?

A) methanoic propanoic anhydride

B) formic propionic anhydride

C) ethanoic propionic anhydride

D) acetic butyric anhydride

E) butanoic ethanoic anhydride

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

67) What is the structure of acetic formic anhydride?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

68) What is the IUPAC name for the compound shown?

A) hexanoic anhydride

B) septanoic anhydride

C) propanoic anhydride

D) dipropanoic carboxyl ether

E) dipropanone

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

69) Provide the structure for benzoic ethanoic anhydride.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

70) What is the IUPAC name for the compound shown?

A) sec-butyl ethanoate

B) ethyl 3-methylpentanoate

C) 3-methylbutyl ethanoate

D) ethyl 3-methylbutanoate

E) none of these

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

71) What is the IUPAC name for the compound shown?

A) 2-methylbutyl 3-methylbutanoate

B) 3-methylbutyl 3-methylbutanoate

C) 2-methylbutyl isovalerate

D) 2-methylbutyl 2-methylbutanoate

E) isopentyl isovalerate

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

72) What is the IUPAC name for the compound shown?

A) 2-methylbutyl acetate

B) 3-methylbutyl acetate

C) 2-methylbutyl methanoate

D) 3-methylbutyl methanoate

E) isopentyl formate

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

73) What is the common name for the compound shown?

A) 2-methylbutyl acetate

B) 3-methylbutyl acetate

C) 2-methylbutyl methanoate

D) 3-methylbutyl methanoate

E) isopentyl formate

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

74) What is the IUPAC name for the following compound?

A) 3-cyclohexyl-2-oxy-tert-butanone

B) butyl cyclohexanecarboxylate

C) butyl cyclohexanone

D) t-butyl cyclohexanone

E) t-butyl cyclohexanecarboxylate

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

75) Provide the structure for benzyl propionate.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

76) What is the structure of N-phenyl-N-propyl-2,3-dimethylbutanamide?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

77) What is the structure of N-methylcyclohexanecarboxamide?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

78) What is the IUPAC name for the compound shown?

A) N,N-diethylbenzamine

B) N,ethylbenzamine

C) N-ethylbenzamide

D) 1-benzyl, 1-aminodiethyl ketone

E) N,N-diethylbenzamide

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

79) What is the common name for the compound shown?

A) benzaldehyde

B) N,N-diethylacetamide

C) benzylamine

D) ketobenzylamide

E) N,N-carboxyamide

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

80) What is the IUPAC name for the compound shown?

A) N,N-diethylethanamine

B) N,N-diethylethanamide

C) N,ethylpropylamide

D) N-ethylpropylamine

E) N-ethylethanamide

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

81) What is the IUPAC name for the compound shown?

A) 2,3-dimethylbutanenitrile

B) α,β-dimethylbutyrnitrile

C) β,γ-dimethylbutyrnitrile

D) 3,4-dimethylbutanenitrile

E) 3,4-dimethylpentanenitrile

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

82) What is the IUPAC name for the compound shown?

A) 2,2-dimethylbutanenitrile

B) 3,3-dimethylbutanenitrile

C) α,α-dimethylbutyronitrile

D) β,β-dimethylbutyronitrile

E) γ,γ-dimethylbutyronitrile

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

83) What is the common name for the compound shown?

A) 2,2-dimethylbutanenitrile

B) 3,3-dimethylbutanenitrile

C) α,α-dimethylbutyronitrile

D) β,β-dimethylbutyronitrile

E) γ,γ-dimethylbutyronitrile

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

84) What is the structure of 3-ethylbenzonitrile?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

85) What is the IUPAC name for the compound shown?

A) 2-cyanobenzylcyclohexane

B) 2-bromo-1-cyanocyclohexane

C) 2-bromocyanocyclohexane

D) 2-bromocyclohexanecarbonitrile

E) 2-bromocyclohexanenitrile

Diff: 2

Learning Objective: 20.6 List four types of carboxylic acid derivatives and explain how each is named

86) Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

A) I > IV > III > II

B) II > III > IV > I

C) I > III > II > IV

D) III > IV > II > I

E) IV > I > III > II

Diff: 2

Learning Objective: 20.7 Compare the reactivity of carboxylic acid derivatives, and describe the mechanism of a nucleophilic acyl substitution reaction

87) Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

A) I > IV > III > II

B) II > III > IV > I

C) I > III > II > IV

D) III > IV > II > I

E) IV > I > III > II

Diff: 2

Learning Objective: 20.7 Compare the reactivity of carboxylic acid derivatives, and describe the mechanism of a nucleophilic acyl substitution reaction

88) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

89) What is the predicted product of the reaction shown?

A) 3-methylbutanoyl chloride

B) 2-methylbutanoyl chloride

C) 2-methylpropanoyl chloride

D) 3-methylbutanoic acid

E) 2-methylbutanoic acid

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

90) What is the predicted product of the reaction shown?

A) ethyl 3-methylbutanoate

B) ethyl 2-methylpropanoate

C) isobutyl ethanoate

D) 5-methyl-3-hexanone

E) none of these

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

91) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

92) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

93) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

94) What reagents are necessary to carry out the conversion shown?

4-ethylheptanoyl chloride → 5-ethyl-2-octanone

A) CH3Li

B) CH3MgBr

C) (CH3)2CuLi

D) 1. Mg/ether

2. CH3Br

E) CH3OH

Diff: 2

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

95) What reagents are necessary to carry out the conversion shown?

A) A. Na2Cr2O7/H2SO4 B. SOCl2; C. CuLi

B) A. Na2Cr2O7/H2SO4/H2O; B. SOCl2; C. (CH3CH2CH2CH2)2CuLi

C) A. Na2Cr2O7/H2SO4/H2O; B. H2SO4; C. (CH3CH2CH2)2CuLi

D) A. Na2Cr2O7; B. H2O; C. (CH3CH2CH2)2CuLi

E) A. Na2Cr2O7/H2SO4/H2O; B. SOCl2; C. (CH3CH2CH2)2CuLi

Diff: 3

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

96) What reagents are necessary to carry out the conversion shown?

A) 1. Na2Cr2O7/H2SO4/H2O; 2. CH3CH2CH2CH2MgBr; 4. H2O

B) 1. Na2Cr2O7/H2SO4/H2O; 2. SOCl2; 3. excess CH3CH2CH2CuLi; 4. H2O

C) 1. Na2Cr2O7/H2SO4; 2. excess CH3CH2MgBr; 4. H3O+

D) 1. Na2Cr2O7/H2SO4/H2O; 2. SOCl2; 3. excess CH3CH2MgBr; 4. H2O

E) 1. Na2Cr2O7; 2. SOCl2; 3. CH3CH2MgBr; 4. H2O

Diff: 3

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

97) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

98) What reagents are needed to convert 4,5-dimethyl-1-hexanol into N-cyclopentyl-4,5-dimethylhexanamide?

A) 1. Na2Cr2O7/H2SO4/H2O; 2.

B) 1. SOCl2; 2. K2Cr2O7/H2SO4/H2O; 3.

C) 1. K2Cr2O7/H2SO4/H2O; 2. SOCl2; 3.

D) 1. ; 2. K2Cr2O7/H2SO4/H2O; 3. SOCl2

E) 1. K2Cr2O7/H2SO4/H2O; 2. SOCl2

Diff: 3

Learning Objective: 20.8 Identify the reagents necessary to prepare an acid chloride from a carboxylic acid, and predict the products for the reactions of acid chlorides with water, alcohol, ammonia, LAH, or a Grignard reagent

99) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

100) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

101) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

102) Which of the reactions shown would not yield isopropyl acetate as major product?

A) I

B) II

C) III

D) IV

E) I and III

Diff: 2

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

103) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

104) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

105) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

106) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

107) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

108) What reagent is necessary to carry out the conversion shown?

A) SOCl2

B) CH3Br

C) CH3CH2MgBr

D) LiAlH4

E) [(CH3)2CH]2CuLi

Diff: 2

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

109) What reagents are necessary to carry out the reaction sequence shown?

A) A. K2Cr2O7/H2SO4/H2O; B. high heat; C. excess CH3CH2MgBr followed by H2O

B) A. K2Cr2O7/H2SO4/H2O; B. ultraviolet light; C. excess CH3CH2MgBr followed by H2O

C) A. K2Cr2O7/H2SO4/H2O; B. high heat; C. 1 equiv. CH3MgBr followed by H2O

D) A. PBr3; B. high heat; C. excess CH3MgBr followed by H2O

E) A. Excess LiAlH4; B. high heat; C. excess CH3Br followed by H2O

Diff: 3

Learning Objective: 20.9 Identify the reagents necessary to prepare an acid anhydride from a carboxylic acid, and predict the products for the reactions of acid anhydrides with water, alcohol, ammonia, LAH, or a Grignard reagent

110) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides

111) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides

112) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides

113) Which of the reactions shown would not yield propyl butanoate as its major product?

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 20.10 Identify how esters can be prepared from either carboxylic acids or from acid chlorides

114) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) A and B

E) A and C

Diff: 3

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

115) What is(are) the predicted products of the reaction shown?

A) I

B) II

C) III

D) A and B

E) A and C

Diff: 3

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

116) What reagents are necessary to carry out the conversion shown?

A) NaBH4/CH3OH

B) Na/NH3

C) 1. LiAlH4

2. H2O

D) H3O+/heat

E) A and C

Diff: 2

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

117) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

118) What reagents are necessary to carry out the conversion shown?

A) 1. (CH3)2CuLi

2. H2O

B) 1. excess DIBAH

2. H2O

C) 1. excess CH3MgBr

2. H2O

D) Both A and C

Diff: 3

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

119) What is(are) the predicted products of the reaction shown?

A) I

B) II

C) III

D) A and B

E) A, B, and C

Diff: 3

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

120) What reagent(s) is(are) required to carry out the conversion shown?

A) (CH3)2CHOH only

B) (CH3)2CHOH/H2SO4

C) CH3CH2OH/H2SO4

D) CH3CH2OH only

E) H2SO4 only

Diff: 3

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

121) Barbital, used as a sedative, is synthesized from diethyl 2,2-diethyl malonate (A) and urea (B). What is the structure of barbital?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.11 Predict the products for the reactions of esters, including hydrolysis, aminolysis, reduction, and nucleophilic attack by a Grignard reagent

122) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

123) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

124) What reagents are necessary to carry out the conversion shown?

A) 1. H3O+/heat; 2. SOCl2/pyridine; 3. CH3OH/pyridine

B) 1. PBr3; 2. CH3CH2MgBr; 3.H2O; 4. acetone

C) 1. PBr3; 2. CH3CH2MgBr; 3.H2O; 4.

D) 1. H3O+/heat; 2. SOCl2/pyridine; 3.

E) 1. H3O+/heat; 2. pyridine; 3.

Diff: 3

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

125) What reagents are necessary to carry out the conversion shown?

A) 1. H3O+, heat; 2. CH3CH2OH, H2SO4

B) 1. H3O+; 2. CH3OH, H2SO4

C) 1. SOCl2; 2. heat; 3. CH3CH2OH, H2SO4

D) 1. LiAlH4; 2. SOCl2; 3. CH3CH2OH, H2SO4

E) 1. H2SO4, heat; 2. CH3OH, H2SO4

Diff: 2

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

126) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) I and II

Diff: 3

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

127) Aspartame is an artificial sweetener used in Equal® and diet soft drinks. What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) A and B

E) A, B, and C

Diff: 3

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

128) What reagents are necessary to carry out the conversion shown?

A) 1. NH3; 2. LiAlH4; 3. H2O

B) 1. (CH3)2NH; 2. LiAlH4; 3. H2O

C) 1. SOCl2; 2. (CH3)2NH; 3. H2O

D) 1. (CH3)2NH; 2. heat; 3. H2O

E) 1. CH3NH; 2. LiAlH4; 3. H2O

Diff: 3

Learning Objective: 20.12 Identify how amides are prepared and how they can be converted to carboxylic acids or to amines

129) What reagents are necessary to carry out the conversion shown?

A) 1. CH3Cl/AlCl3

2. Br2/hν

3. NaCN

B) 1. CH3Cl/AlCl3

2. HCN

C) 1. Br2/FeBr3

2. Mg/ether

3. CO2

4. H3O+

5. SOCl2

6. excess NH3

7. SOCl2

D) A and C

E) A and B

Diff: 3

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

130) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

131) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

132) What reagents are necessary to carry out the conversion shown?

A) 1. (CH3)2CH2CH2MgBr; 2. H3O+

B) 1. (CH3)2CHMgBr; 2. H3O+

C) 1. (CH3)2CHBr; 2. H3O+

D) 1. LiAlH4; 2. (CH3)2CHMgBr

E) 1. (CH3)2CHMgBr

Diff: 3

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

133) What reagents are necessary to carry out the conversion shown?

A) 1. NH3; 2. H3O+

B) 1. LiAlH4; 2. H2O

C) 1. H2SO4; 2. H3O+

D) 1. LiAlH4; 2. NH3

E) 1. LiAlH4; 2. KCN

Diff: 2

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

134) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

135) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.13 Identify two methods of preparing nitriles and show how nitriles can be converted to carboxylic acids, ketones, and amines

136) What is an appropriate stepwise synthesis for the conversion shown?

A) 1. Mg/ether; 2. CO2; 3. H3O+; 4. SOCl2; 5. (CH3CH2)2CuLi

B) 1. Mg/ether; 2. H3O+; 3. (CH3CH2)2CuLi

C) 1. Mg/ether; 2. CH3CH2CN; 3. H3O+

D) A or B

E) A or C

Diff: 3

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives

137) What is an appropriate stepwise synthesis for the following synthesis that uses ethyl 3-methylbutanoate as the only source of carbon and using any other reagents necessary?

A) 1. PBr3; 2. Mg/ether; 3. SOCl2; 4. 2 equiv. CH3CH2MgBr; 5. H2O

B) 1. H3O+/heat; 2. SOCl2; 3. 2 equiv. CH3CH2MgBr; 4. H2O

C) 1. PBr3; 2. H3O+/heat; 3. H2SO4; 4. MgBr; 5. SOCl2; 6. CH3CH2MgBr; 7. H2O

D) 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. SOCl2; 5. 2 equiv. CH3MgBr; 6. H2O

E) 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. 2 equiv. CH3CH2MgBr; 5. H2O

Diff: 3

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives

138) What is an appropriate stepwise synthesis for the following synthesis that uses ethyl 3-methylbutanoate as the only source of carbon and using any other reagents necessary?

A) 1. PBr3; 2. 2 Li; 3. CuI; 4. SOCl2; 5. 1 mole (CH3CH2)2CuLi

B) 1. H3O+/heat; 2. SOCl2; 3. 1 mole (CH3CH2)2CuLi

C) 1. H3O+/heat; 2. PBr3; 3. Li; 4. SOCl2; 5. 1 mole (CH3CH2)2CuLi; 6. H2O

D) 1. H3O+/heat; 2. Mg/ether; 3. SOCl2; 4. CH3CH2MgBr; 5. H2O

E) 1. H3O+/heat; 2. PBr3; 3. Mg/ether; 4. SOCl2; 5. 2 equiv. CH3CH2MgBr; 6. H2O

Diff: 3

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives

139) What is an appropriate stepwise synthesis for 2-phenylethanoyl chloride that uses toluene and/or carbon dioxide as the only source(s) of carbon and any other reagents necessary?

A) 1. Br2/hv; 2. MgBr; 3. CO2; 4. H3O+; 5. SOCl2

B) 1. HBr; 2. MgBr; 3. CO2; 4. H3O+; 5. SOCl2

C) 1. HBr; 2. Mg/ether; 3. CO2; 4. H3O+; 5. SOCl2

D) 1. Br2/hv; 2. Mg/ether; 3. CO2; 4. H3O+; 5. SOCl2

E) 1. Br2/hv; 2. Mg/ether; 3. CO2; 4. SOCl2

Diff: 3

Learning Objective: 20.14 Identify reagents necessary to achieve functional group interconversion of carboxylic acid derivatives

140) A compound with molecular formula C6H12O2 exhibits two singlets in its 1H NMR spectrum, at δ 1.4 (9H) and δ 2.0 (3H). Its IR spectrum shows a strong absorption band near 1740 cm-1. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy

141) A compound with molecular formula C8H14O4 exhibits a triplet at δ 1.3 (6H), a singlet at δ 2.6 (4H) and a quartet at δ 4.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows a strong absorption band near 1740 cm-1. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy

142) A compound with molecular formula C9H10O2 exhibits a triplet at δ 1.2 (3H), a quartet at δ 2.6 (2H), a doublet at δ 7.3 (2H), a doublet at δ 8.0 (2H) and a singlet at δ 11 (1H) in its 1H NMR spectrum. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy

143) A compound with molecular formula C8H14O3 exhibits a triplet at δ 1.0 (6H), a sextet at δ 1.6 (4H) and a triplet at δ 2.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm-1. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.15 Describe the signals produced by carboxylic acid derivatives in IR, 1H NMR, and C NMR spectroscopy

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