Chapter 18 Carbonyl Reactions Enols Test Bank Docx

Package Title: Solomons Test Bank

Course Title: Solomons 12e

Chapter Number: 18

Question type: Multiple Choice

1) Which of the compounds listed below is more acidic than 1-butanol?

a) Ethyl acetoacetate

b) 2-Butanone

c) Ethyl pentanoate

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

2) Which of the compounds listed below is more acidic than 1-butanol?

a) Diethylmalonate

b) 2-Butanone

c) Ethyl pentanoate

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

3) Which of the compounds listed below is more acidic than 1-butanol?

a) Malonic ester

b) 2-Butanone

c) Ethyl pentanoate

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

4) Which of the compounds listed below is more acidic than 1-butanol?

a) Ethyl 2-oxocyclohexanecarboxylate

b) 2-Butanone

c) Ethyl pentanoate

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

5) Which of the compounds listed below is more acidic than 2-pentanol?

a) Ethyl 3-oxopentanoate

b) 2-Pentanone

c) Pentanal

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

6) Which of the compounds listed below is more acidic than 2-pentanol?

a) Diethyl malonate

b) 2-Pentanone

c) Pentanal

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

7) Which of the compounds listed below is more acidic than 2-pentanol?

a) Malonic ester

b) 2-Pentanone

c) Pentanal

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

8) Which of the compounds listed below is more acidic than 2-pentanol?

a) Ethyl 2-oxocyclohexanecarboxylate

b) 2-Pentanone

c) Pentanal

d) All of these choices.

e) Two of these choices.

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

9) Which of the following hydrogens is the most acidic?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

10) Which is the most acidic hydrogen in the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

11) Which is the most acidic hydrogen in the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

12) Which is the most acidic hydrogen in the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

13) Which is the most acidic hydrogen in the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

14) Which is the most acidic hydrogen in the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

15) Which is the most acidic hydrogen in the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

16) Which of the following compounds is the strongest acid?

a) I

b) II

c) III

d) IV

e) V

Topic: Relative Acidities

Section: 18.1

Difficulty Level: Medium

17) Which compound contains the most acidic hydrogens?

a) CH₃CH₂CH₃

b) CH₃CHCH₂

c) Cyclohexane

d) (CH₃)₂C=O

e) Benzene

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

18) Considering only the highlighted hydrogens, list the following compounds in order of increasing acidity:

a) IV, II, III, I, V

b) II, V, IV, I, III

c) III, I, IV, II, V

d) IV, V, II, I, III

e) V, IV, III, II, I

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

19) Considering only the highlighted hydrogens, list the following compounds in order of decreasing acidity:

a) I, II, III, IV, V

b) III, V, IV, I, II

c) III, I, II, V, IV

d) IV, V, II, I, III

e) V, IV, III, II, I

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

20) Considering only the highlighted hydrogens, list the following compounds in order of increasing acidity:

a) I, II, III, IV, V

b) II, V, III, I, IV

c) III, I, IV, II, V

d) IV, V, II, I, III

e) V, II, III, I, IV

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

21) Considering only the highlighted hydrogens, list the following compounds in order of decreasing acidity:

a) I, II, III, IV, V

b) II, V, III, I, IV

c) IV, I, III, II, V

d) IV, V, II, I, III

e) V, IV, III, II, I

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

22) Considering only the highlighted hydrogens, list the following compounds in order of increasing acidity:

a) I, II, III, IV, V

b) II, V, III, I, IV

c) III, I, IV, II, V

d) IV, V, II, I, III

e) V, II, III, I, IV

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

23) Considering only the highlighted hydrogens, list the following compounds in order of decreasing acidity:

a) I, II, III, IV, V

b) II, V, III, I, IV

c) IV, I, III, II, V

d) IV, V, II, I, III

e) V, IV, III, II, I

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

24) Which structure represents an ester enolate?

a) I

b) II

c) III

d) IV

e) Two of these choices.

Topic: Enolates

Section: 18.1

Difficulty Level: Medium

25) Which of the following is a keto-enol tautomeric pair?

a) I

b) II

c) III

d) IV

e) V

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

26) Which of the following is a keto-enol tautomeric pair?

a) I

b) II

c) III

d) IV

e) V

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

27) Which of the following is a keto-enol tautomeric pair?

a) I

b) II

c) III

d) IV

e) V

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

28) Which of the following represent tautomers?

a)

b)

c)

d) All of these choices.

e) None of these choices.

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

29) Which of these compounds would exist in an enol form to the greatest extent?

a)

b)

c)

d)

e)

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

30) Which of the following represent keto-enol tautomers?

a)

b)

c)

d) More than one of these choices.

e) None of these choices.

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

31) Simple enols are less stable than the tautomeric keto forms because:

a) severe angle strain exists in the enol forms.

b) fewer atoms are coplanar in the keto form.

c) the enol cannot be chiral.

d) the C-C  bond is weaker than the C-O  bond.

e) Actually, simple enols are the more stable.

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Medium

32) Which of these compounds would exist primarily in an enol form?

a)

b)

c)

d)

e)

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Medium

33) Which of these compounds would exist primarily in an enol form?

a)

b)

c)

d)

e)

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Medium

34) Which of these compounds would exist primarily in an enol form?

a)

b)

c)

d)

e)

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Hard

35) Which of these compounds would exist primarily in an enol form?

a)

b)

c)

d)

e)

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Hard

36) Which of the following would undergo racemization in base?

a) I

b) II

c) III

d) IV

e) Both III and IV

Topic: Racemization

Section: 18.3

Difficulty Level: Easy

37) Which of the following would undergo epimerization in base?

a) I

b) II

c) III

d) IV

e) Both III and IV

Topic: Racemization/Epimerization

Section: 18.3

Difficulty Level: Easy

38) Which of the following would undergo epimerization in acid?

a) I

b) II

c) III

d) IV

e) Both III and IV

Topic: Racemization/Epimerization

Section: 18.3

Difficulty Level: Easy

39) Which of the following would undergo racemization in base?

a) I

b) II and III

c) IV and V

d) I and V

e) I, IV and V

Topic: Racemization

Section: 18.3

Difficulty Level: Medium

40) Which of the following would not undergo racemization in base?

a) (S)-2-phenylbutanal

b) (S)-3-phenylbutanal

c) (S)-3-phenyl-2-butanone

d) (S)-3-methyl-2-phenylbutanal

e) All of these choices will undergo racemization in base.

Topic: Racemization

Section: 18.3

Difficulty Level: Hard

41) Which of these halides is predicted to alkylate malonic ester (as the anion) in highest yield?

a) CH₃I

b) C₆H₅Br

c) (CH₃)₃CCH₂Cl

d) CH₃CHClCH₃

e) All of these choices should be equally effective.

Topic: Reaction Products

Section: 18.7

Difficulty Level: Easy

42) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

43) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

44) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

46) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

47) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

48) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Easy

49) What would be the major product of the following reaction?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

50) What would be the major product of the following reaction?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

51) Which would be formed when 2-methylpropanal is dissolved in D₂O containing NaOD?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

52) Which would be formed when 2-methylpropanal is dissolved in T₂O containing NaOT?

a)

b)

c)

d)

e) None of these choices.

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

53) Which would be formed when 2-methylpropanal is dissolved in D₂O containing D⁺?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

54) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

55) Which compound would be formed when 2-methylbutanal is treated with a solution of NaOD in D₂O?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

56) Which compound would be formed when 2-methylbutanal is treated with a solution of NaOT in T₂O?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

57) Which compound would be formed when 2-methylbutanal is treated with a solution of D⁺ in D₂O?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

58) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of NaOD in D₂O?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

59) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of NaOT in T₂O?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

60) Which compound would be formed when 2,3-dimethylhexanal is treated with a solution of D⁺ in D₂O?

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

61) Which of the following would not undergo racemization in base?

a) (R)-3-methyl-4-heptanone

b) (R)-3-methyl-2-heptanone

c) (R)-4-methyl-2-heptanone

d) (R)-2,4-dimethyl-3-heptanone

e) All of these choices will undergo racemization in base.

Topic: Racemization

Section: 18.3

Difficulty Level: Hard

62) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 7.6 and 18.3

Difficulty Level: Medium

63) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 7.6 and 18.3

Difficulty Level: Medium

64) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

65) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 7.6 and 18.3

Difficulty Level: Medium

66) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

67) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

68) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

69) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

70) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

71) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

72) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

73) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Medium

74) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.3

Difficulty Level: Medium

75) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Medium

76) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Medium

77) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Medium

78) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Medium

79) Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl bromide, potassium tert-butoxide, isobutyl chloride, hot aqueous NaOH, HCl, and heat. What is the final product?

a) 4-Ethyl-2-methylpentanoic acid

b) 6-Methylheptanoic acid

c) 2-Ethyl-3-methylpentanoic acid

d) 2-Ethyl-4-methylpentanoic acid

e) Ethylisobutylmalonic acid

Topic: Reaction Products

Section: 18.7

Difficulty Level: Hard

80) Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), 1-bromopentane, potassium tert-butoxide, iodomethane, hot aqueous NaOH, HCl, and heat. What is the final product?

a) 2-Methylheptanoic acid

b) 3-Methylhexanoic acid

c) 3-Methylpentanoic acid

d) 2-Methylpentanoic acid

e) Ethyl 2-methylheptanoate

Topic: Reaction Products

Section: 18.7

Difficulty Level: Hard

81) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Hard

82) What product is finally formed when the initial compound formed from cyclohexanone and pyrrolidine is mixed with allyl chloride and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

83) What product is finally formed when the initial compound formed from cyclohexanone and piperidine is mixed with allyl chloride and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

84) What product is finally formed when the initial compound formed from cyclohexanone and piperidine is mixed with methyl iodide and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

85) What product is finally formed when the initial compound formed from cyclohexanone and morpholine is mixed with allyl chloride and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

86) What product is finally formed when the initial compound formed from cyclohexanone and morpholine is mixed with methyl iodide and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

87) What product is finally formed when the initial compound formed from cyclopentanone and piperidine is mixed with allyl chloride and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

88) What product is finally formed when the initial compound formed from cyclopentanone and piperidine is mixed with methyl iodide and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

89) What product is finally formed when the initial compound formed from cyclopentanone and piperidine is mixed with benzyl chloride and that product is heated and then hydrolyzed?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.9

Difficulty Level: Hard

90) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 18.4

Difficulty Level: Hard

91) What synthetic strategy would accomplish the following transformation?

a) i) Br₂, H₃O⁺; ii) NaOC₂H₅, C₂H₅OH, heat

b) i) Cl₂, FeCl₃; ii) NaOC₂H₅, C₂H₅OH, heat

c) i) HCN; ii) H₃O⁺_, heat

d) i) Br₂, h; ii) (CH₃)₃COK, (CH₃)₃COH, heat

e) None of these choices.

Topic: Synthetic Strategy

Section: 7.6 and 18.3

Difficulty Level: Hard

92) Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone?

a) NaOI (I₂ in NaOH)

b) Br₂/CCl₄

c) CrO₃/H₂SO₄

d) NaHCO₃/H₂O

e) Ag(NH₃)₂⁺

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

93) Which reagent would best serve as the basis for a simple chemical test to distinguish between acetophenone and propiophenone?

a) NaOI (I₂ in NaOH)

b) Br₂/CCl₄

c) CrO₃/H₂SO₄

d) NaHCO₃/H₂O

e) Ag(NH₃)₂⁺

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

94) Which reagent would best serve as the basis for a simple chemical test to distinguish between acetophenone and benzophenone?

a) NaOI (I₂ in NaOH)

b) Br₂/CCl₄

c) CrO₃/H₂SO₄

d) NaHCO₃/H₂O

e) Ag(NH₃)₂⁺

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

95) Which reagent would best serve as the basis for a simple chemical test to distinguish between m-chloroacetophenone and m-chloropropiophenone?

a) NaOI (I₂ in NaOH)

b) Br₂/CCl₄

c) CrO₃/H₂SO₄

d) NaHCO₃/H₂O

e) Ag(NH₃)₂⁺

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

96) Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-1-propanol and 2-butanol?

a) NaOI (I₂ in NaOH)

b) KMnO₄ in H₂O

c) Br₂ in CCl₄

d) Cold concd H₂SO₄

e) CrO₃ in H₂SO₄

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

97) Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between isopropyl alcohol and isobutyl alcohol?

a) NaOI (I₂ in NaOH)

b) KMnO₄ in H₂O

c) Br₂ in CCl₄

d) Cold concd H₂SO₄

e) CrO₃ in H₂SO₄

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

98) A compound, C₅H₁₀O, reacts with phenylhydrazine and gives a positive iodoform test. The compound could be which of these?

a)

b)

c) CH₂=CHCH₂CHOHCH₃

d)

e)

Topic: Chemical Tests

Section: 18.3

Difficulty Level: Medium

99) Which reagent would best serve as the basis for a simple chemical test to distinguish between

a) NaOI (I₂ in NaOH)

b) Br₂/CCl₄

c) CrO₃/H₂SO₄

d) NaHCO₃/H₂O

e) Ag(NH₃)₂⁺

Topic: Chemical Tests

Section: 8.12 and 18.3

Difficulty Level: Hard

100) Which reagent would best serve as the basis for a simple chemical test to distinguish between CH₃CHO and CH₃COCH₃?

a) NaOI (I₂ in NaOH)

b) Br₂/CCl₄

c) C₆H₅NHNH₂

d) NaHCO₃/H₂O

e) Ag(NH₃)₂⁺

Topic: Chemical Tests

Section: 16.12 and 18.3

Difficulty Level: Hard

101) A compound, X, C₉H₁₀O, which reacts with I₂/NaOH to give a pale yellow precipitate, gives the following ¹H NMR spectrum.

Singlet, 2.0

Singlet, 3.0

Multiplet, 7.7

Which is a possible structure for X?

a) I

b) II

c) III

d) IV

e) V

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3

Difficulty Level: Medium

102) A compound, X, C₉H₁₀O, which reacts with I₂/NaOH to give a pale yellow precipitate, gives the following ¹H NMR spectrum.

Singlet, 2.38

Singlet, 2.54

Multiplet (centered), 7.50

Which is a possible structure for X?

a) I

b) II

c) III

d) IV

e) V

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3

Difficulty Level: Medium

103) The conversion of is accomplished by the use of which oxidizing agent?

a) Ag(NH₃)₂⁺

b) O₃

c) NaOI (I₂ in NaOH)

d)

e) Cu²⁺

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3

Difficulty Level: Medium

104) The conversion of is accomplished by the use of which oxidizing agent?

a) Ag(NH₃)₂⁺

b) O₃

c) NaOCl (Cl₂ in NaOH)

d)

e) Cu²⁺

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3

Difficulty Level: Medium

105) The conversion of is accomplished by the use of which oxidizing agent?

a) Ag(NH₃)₂⁺

b) O₃

c) NaOBr (Br₂ in NaOH)

d)

e) Cu²⁺

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3

Difficulty Level: Medium

106) Which compound could be subjected to a haloform reaction to produce m-chlorobenzoic acid?

a) I

b) II

c) III

d) IV

e) V

Topic: Reagents, Intermediates, and Spectroscopy

Section: 18.3

Difficulty Level: Medium

107) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

108) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

109) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

110) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

111) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

112) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

113) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

114) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

115) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

116) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

117) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

118) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

119) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

120) What would be the major product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.3

Difficulty Level: Medium

121) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Medium

122) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Medium

123) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Medium

124) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Medium

125) Predict the product of the following reaction sequence.

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

126) What would be the product, P, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

127) 2-Heptanone can be synthesized by which reaction sequence?

a)

b)

c)

d)

e)

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

128) What is the product, W, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

129) What is the product, W, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

130) What is the product, W, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

131) What is the product, W, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

132) What is the product, W, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

133) What is the product, L, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

134) What is the product, L, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Medium

135) What is the product, Z, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.9

Difficulty Level: Medium

136) What is the product, Z, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.9

Difficulty Level: Medium

137) What is the product, Z, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.9

Difficulty Level: Medium

138) What is the product, Z, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.9

Difficulty Level: Medium

139) What is the product, Z, of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.9

Difficulty Level: Medium

140) Which product can be obtained via the following generalized reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.7

Difficulty Level: Hard

141) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Hard

142) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Hard

143) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Hard

144) What would be the major product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 18.4

Difficulty Level: Hard

145) Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?

a) Sodium methoxide

b) Sodium ethoxide

c) Sodium hydride

d) Potassium tert-butoxide

e) Lithium diisopropylamide

Topic: General Information

Section: 18.4

Difficulty Level: Medium

146) Which base is employed in the alkylation of ethyl pentanoate with methyl iodide?

a) Sodium methoxide

b) Sodium ethoxide

c) Sodium hydride

d) Potassium tert-butoxide

e) Sodium amide

Topic: General Information

Section: 18.4

Difficulty Level: Medium

147) Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

a) Sodium methoxide

b) Sodium ethoxide

c) Sodium hydride

d) Potassium tert-butoxide

e) Lithium diisopropylamide

Topic: General Information

Section: 18.4

Difficulty Level: Medium

148) Which base is employed in the alkylation of methyl hexanoate with ethyl iodide?

a) Sodium methoxide

b) Sodium ethoxide

c) Sodium hydride

d) Potassium tert-butoxide

e) Sodium amide

Topic: General Information

Section: 18.4

Difficulty Level: Medium

149) Consider the synthesis below. What is compound Z?

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 18.7

Difficulty Level: Medium

150) What combination of reagents can be used to make the following substance via an enamine?

a) I

b) II

c) III

d) IV

e) Both reactions II and III

Topic: Synthesis

Section: 18.9

Difficulty Level: Medium

151) What combination of reagents can be used to make the following substance via an enamine?

a) I

b) II

c) III

d) IV

e) None of these reagents can be used.

Topic: Synthesis

Section: 18.9

Difficulty Level: Medium

152) What combination of reagents can be used to make the following substance via an enamine?

a) I

b) II

c) III

d) IV

e) None of these reagents can be used.

Topic: Synthesis

Section: 18.9

Difficulty Level: Medium

153) Which of the following would provide the best synthesis of 3,5-dimethyl-2-hexanone?

a) Ethyl acetoacetate + NaOC₂H₅ + CH₃I; then KO-t-Bu + (CH₃)₃CCH₂Br; then NaOH; then H₃O⁺; then heat

b) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₃CBr; then KO-t-Bu + CH₃I; then NaOH; then H₃O⁺; then heat

c) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂Br; then KO-t-Bu + CH₃I; then NaOH; then H₃O⁺; then heat

d) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CHBrCH₃; then NaOH; then H₃O⁺; then heat

e) Ethyl acetoacetate + NaOC₂H₅ + CH₃I; then KO-t-Bu + (CH₃)₂CHBr; then NaOH; then H₃O⁺; then heat

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

154) Which of the following would provide the best synthesis of 3-ethyl-6-methyl-2-heptanone?

a) Ethyl acetoacetate + NaOC₂H₅ + CH₃CH₂I; then KO-t-Bu + (CH₃)₃CCH₂CH₂Br; then NaOH; then H₃O⁺; then heat

b) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₃CCH₂Br; then KO-t-Bu + CH₃CH₂I; then NaOH; then H₃O⁺; then heat

c) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CH₂Br; then KO-t-Bu + CH₃CH₂I; then NaOH; then H₃O⁺; then heat

d) Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CH₂CHBrCH₂CH₃; then NaOH; then H₃O⁺; then heat

e) Ethyl acetoacetate + NaOC₂H₅ + CH₃CH₂I; then KO-t-Bu + (CH₃)₂CHCH₂Br; then NaOH; then H₃O⁺; then heat

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

155) Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl malonate?

a) Bromoethane, 1-bromopropane, sodium ethoxide, and potassium tert-butoxide

b) 3-Bromohexane and sodium ethoxide

c) 3-Bromopentane and sodium ethoxide

d) Bromoethane, 2-bromopropane, sodium ethoxide, and potassium tert-butoxide

e) 2-Bromopentane and sodium ethoxide

Topic: Synthesis

Section: 18.7

Difficulty Level: Hard

156) Which organic reagents would you need to make 2-ethylheptanoic acid from diethyl malonate?

a) Bromoethane, 1-bromopentane, sodium ethoxide, and potassium tert-butoxide

b) 3-Bromooctane and sodium ethoxide

c) 3-Bromoheptane and sodium ethoxide

d) 1-Bromopropane, 2-bromopentane, sodium ethoxide, and potassium tert-butoxide

e) 2-Bromoheptane and potassium tert-butoxide

Topic: Synthesis

Section: 18.7

Difficulty Level: Hard

157) Which of the following could be used to synthesize the following substance in good yield?

a) Cyclohexanone, ClCH₂COOH, AlCl₃, heat

b) Cyclohexanone, (CH₃CH₂)₂NH, HA, (-H₂O); then BrCH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

c) Cyclohexylacetic acid, KMnO₄, OH^–, heat; then H₃O⁺

d) Two of these choices.

e) All of these choices.

Topic: Synthesis

Section: 18.9

Difficulty Level: Hard

158) Which of the following could be used to synthesize the following substance in good yield?

a) Cyclohexanone, ClCH₂COOH, AlCl₃, heat

b) Cyclohexanone, (CH₃)₂NH, HA, (-H₂O); then BrCH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

c) Cyclohexylacetic acid, KMnO₄, OH^­, heat; then H₃O⁺

d) Two of these choices.

e) All of these choices.

Topic: Synthesis

Section: 18.9

Difficulty Level: Hard

159) Which of the following could be used to synthesize the following substance in good yield?

a) Cyclohexanone, ClCH₂COOH, AlCl₃, heat

b) Cyclohexanone, pyrrolidine, HA, (-H₂O); then BrCH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

c) Cyclohexylacetic acid, KMnO₄, OH^–, heat; then H₃O⁺

d) Two of these choices.

e) All of these choices.

Topic: Synthesis

Section: 18.9

Difficulty Level: Hard

160) Which of the following could be used to synthesize the following substance in good yield?

a) Cyclopentanone, ClCH₂CH₂COOH, AlCl₃, heat

b) Cyclopentanone, (CH₃CH₂)₂NH, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

c) 3-(2-Hydroxycyclopentyl)propanal, KMnO₄, OH^–, heat; then H₃O⁺

d) Cyclopentanone, ClCH₂CH₂COOH, AlCl₃, heat and cyclopentanone, (CH₃CH₂)₂NH, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

e) Cyclopentanone, (CH₃CH₂)₂NH, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺ and 3-(2-hydroxycyclopentyl)propanal, KMnO₄, OH^–, heat; then H₃O⁺

Topic: Synthesis

Section: 18.9

Difficulty Level: Hard

161) Which of the following could be used to synthesize the following substance in good yield?

a) Cyclopentanone, ClCH₂CH₂COOH, AlCl₃, heat

b) Cyclopentanone, (CH₃)₂NH, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

c) 3-(2-Hydroxycyclopentyl)propanal, KMnO₄, OH^–, heat; then H₃O⁺

d) Cyclopentanone, ClCH₂CH₂COOH, AlCl₃, heat and cyclopentanone, (CH₃)₂NH, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

e) Cyclopentanone, (CH₃)₂NH, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺ and 3-(2-hydroxycyclopentyl)propanal, KMnO₄, OH^–, heat; then H₃O⁺

Topic: Synthesis

Section: 18.9

Difficulty Level: Hard

162) Which of the following could be used to synthesize the following substance in good yield?

a) Cyclopentanone, ClCH₂CH₂COOH, AlCl₃, heat

b) Cyclopentanone, piperidine, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

c) 3-(2-Hydroxycyclopentyl)propanal, KMnO₄, OH^–, heat; then H₃O⁺

d) Cyclopentanone, ClCH₂CH₂COOH, AlCl₃, heat and cyclopentanone, piperidine, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺

e) Cyclopentanone, piperidine, HA, (-H₂O); then BrCH₂CH₂COOC₂H₅; then OH^–, H₂O, heat; then H₃O⁺ and 3-(2-hydroxycyclopentyl)propanal, KMnO₄, OH^–, heat; then H₃O⁺

Topic: Synthesis

Section: 18.9

Difficulty Level: Hard

163) Which of these amines is/are used with aldehydes and ketones to form enamines?

a) I

b) II

c) III

d) IV

e) Both I and II

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Easy

164) Which of these amines is/are used with aldehydes and ketones to form enamines?

a) I

b) II

c) III

d) IV

e) I, II, and II

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Easy

165) Which of these amines is/are used with aldehydes and ketones to form enamines?

a) I

b) II

c) III

d) IV

e) All of these choices.

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Easy

166) Which of the following statements is true of the enamine,

a) The enamine can be made from cyclohexanone + pyrrolidine.

b) It has another resonance structure :

c) It can be acylated at the -carbon of the original carbonyl compound.

d) It can be alkylated.

e) All of these choices are true.

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Medium

167) Which of the following statements is true of the following enamine?

a) The enamine can be made from cyclopentanone + pyrrolidine.

b) It has another resonance structure:

c) It can be acylated at the -carbon of the original carbonyl compound.

d) It can be alkylated.

e) All of these choices are true.

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Medium

Question type: fill-in-the-blank

168) The -hydrogens on carbonyl carbons are unusually acidic (pK_a 19-20) because: ___.

Topic: General, Active Hydrogens

Section: 18.1

Difficulty Level: Easy

169) The pK_a for protons on the carbon between two carbonyls is about 9-11. This greater acidity (as compared to single carbonyl systems) can be accounted for by ___.

Topic: Active Hydrogen Compounds

Section: 18.1

Difficulty Level: Easy

170) Compounds with two electron-withdrawing groups attached to the same carbon atom are known as ___ or ___.

Topic: Active Hydrogen Compounds

Section: 18.1

Difficulty Level: Easy

171) Compounds having two carbonyl groups separated by a carbon atom are called ___.

Topic: Active Hydrogen Compounds

Section: 18.2

Difficulty Level: Easy

Question type: Essay

172) Explain why acylation of active methylene compounds must be carried out in aprotic solvents, typically using NaH to generate the enolate anion: why can sodium ethoxide/ethanol not be used in these reactions?

Topic: Active Hydrogen Compounds

Section: 18.4

Difficulty Level: Medium

Question type: fill-in-the-blank

173) The keto and enol forms of carbonyl compounds are a special type of ___ isomer called ___.

Topic: Keto-Enol Tautomerism

Section: 18.2

Difficulty Level: Easy

174) The interconversion of the keto and enol forms of a carbonyl compound is called ___.

Topic: Keto-Enol Tautomerism

Section: 18.2

Difficulty Level: Easy

Question type: Essay

175) Explain why the following tautomer equilibrium lies far to the right.

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Medium

176) Explain why the following tautomer equilibrium lies far to the right.

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Medium

Question type: fill-in-the-blank

177) Diastereomers that differ in configuration at only one stereogenic center are sometimes called ___, and their interconversion is called ___.

Topic: Epimers

Section: 18.3

Difficulty Level: Medium

178) Dissolving a halogen in aqueous sodium hydroxide provides a solution of ___.

Topic: General

Section: 18.3

Difficulty Level: Easy

179) The haloform reaction is an efficient method for converting methyl ketones to ___.

Topic: Haloform Reaction

Section: 18.3

Difficulty Level: Easy

Question type: Essay

180) When optically active 2-methyl-1-phenyl-1-butanone undergoes reaction with Br₂/H₃O⁺, the product is observed to exhibit no optical activity. Explain clearly.

Topic: Reaction Products: Stereochemical Outcomes

Section: 18.3

Difficulty Level: Hard

Question type: fill-in-the-blank

181) An unsymmetrical ketone can form two possible enolates. The enolate with the more highly substituted double bond is called the ___.

Topic: Kinetic/Thermodynamic Enolates

Section: 18.4

Difficulty Level: Medium

182) The kinetic enolate (the less highly substituted double bond) is favored when ___ is used as a base.

Topic: Kinetic/Thermodynamic Enolates

Section: 18.4

Difficulty Level: Medium

183) Alkylation of an enolate anion must be done using either a primary, primary allylic or primary benzylic species because the substitution follows an ___ mechanistic pathway.

Topic: Alkylation Reactions: Mechanisms

Section: 18.4

Difficulty Level: Easy

Question type: fill-in-the-blank

184) The ethyl acetoacetate anion is the synthetic equivalent of the ___.

Topic: Acetoacetic Ester Synthesis

Section: 18.6

Difficulty Level: Easy

Question type: Essay

185) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Topic: Acetoacetic Ester Synthesis

Section: 18.6

Difficulty Level: Medium

186) When ethyl acetoacetate is treated with one equivalent of ethoxide ion followed by one equivalent of 1,2-dibromoethane compound, X is produced. Treatment of X with a second equivalent of ethoxide, produces Y. Further treatment of this product to conditions of saponification, acidification and heating produced a product, Z, that gives the following spectral data:

¹H NMR: 0.88 δ multiplet ¹³C NMR: Broad Band Decoupled: 10.40, 21.17, 29.84,

208.30 δ

1.00 δ multiplet DEPT 90: 21.17 δ

1.96 δ multiplet DEPT 135: positive signals at 21.17, 29.84 δ

2.24 δ singlet negative signals at 10.40 δ

What is a reasonable structure for Z?

Topic: Reaction Products and Spectroscopy

Section: 18.6

Difficulty Level: Medium

Question type: fill-in-the-blank

187) A reaction of a particular -dicarbonyl compound that gives substituted or disubstituted acetic acids is called the ___.

Topic: Malonic Ester synthesis

Section: 18.7

Difficulty Level: Easy

Question type: Essay

188) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Topic: Malonic Ester synthesis

Section: 18.7

Difficulty Level: Medium

189) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Topic: Malonic Ester Synthesis

Section: 18.7

Difficulty Level: Hard

190) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Topic: Malonic Ester Synthesis

Section: 18.7

Difficulty Level: Hard

191) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Topic: Malonic Ester Synthesis

Section: 18.7

Difficulty Level: Hard

192) What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Topic: Stork Enamine Reaction

Section: 18.9

Difficulty Level: Hard

193) Considering only the highlighted hydrogens, which compound has the most acidic hydrogen:

a) I

b) II

c) III

d) IV

e) V

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

194) Considering only the highlighted hydrogens, which compound has the least acidic hydrogen:

a) I

b) II

c) III

d) IV

e) V

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

195) Considering only the highlighted hydrogens, which compound has the most acidic hydrogen:

a) I

b) II

c) III

d) IV

e) V

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

196) Considering only the highlighted hydrogens, which compound has the least acidic hydrogen:

a) I

b) II

c) III

d) IV

e) V

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

197) Considering only the highlighted hydrogens, which compound has the most acidic hydrogen:

a) I

b) II

c) III

d) IV

e) V

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

198) Considering only the highlighted hydrogens, which compound has the least acidic hydrogen:

a) I

b) II

c) III

d) IV

e) V

Topic: Acid/Base

Section: 18.1

Difficulty Level: Medium

199) Which of these compounds would exist in an enol form to the smallest extent?

a)

b)

c)

d)

e)

Topic: Tautomerization and Keto-Enol Equilibrium

Section: 18.2

Difficulty Level: Easy

200) What is the major product of the following reaction sequence?

a) 2-heptanone

b) ethyl 2-butyl-3-oxobutanoate

c) 2-propanone

d) 2-heptanone

e) none of the choices

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

201) What is the major product of the following reaction sequence?

a) 2-heptanone

b) ethyl 2-butyl-3-oxobutanoate

c) 2-propanone

d) 2-heptanone

e) none of the choices

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

202) What is the major product of the following reaction sequence?

a) 2-heptanone

b) ethyl 2-butyl-3-oxobutanoate

c) 2-propanone

d) 2-heptanone

e) none of the choices

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

203) What is the major product of the following reaction sequence?

a) 2-heptanone

b) ethyl 2-butyl-3-oxobutanoate

c) 2-propanone

d) 2-heptanone

e) none of the choices

Topic: Reaction Sequence

Section: 18.6

Difficulty Level: Medium

204) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + CH₃I; then KO-t-Bu + (CH₃)₃CCH₂Br; then NaOH; then H₃O⁺; then heat

a) 3,5,5-trimethyl-2-hexanone

b) 3,5-dimethyl-2-hexanone

c) 4,6-dimethyl-2-heptanone

d) 4,7-dimethyl-2-octanone

e) 3,4-dimethyl-2-pentanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

205) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₃CBr; then KO-t-Bu + CH₃I; then NaOH; then H₃O⁺; then heat

a) 3,5,5-trimethyl-2-hexanone

b) 2-butanone

c) 3,5-dimethyl-2-hexanone

d) 4,6-dimethyl-2-heptanone

e) 3,4-dimethyl-2-pentanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

206) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂Br; then KO-t-Bu + CH₃I; then NaOH; then H₃O⁺; then heat

a) 3,5,5-trimethyl-2-hexanone

b) 2-butanone

c) 3,5-dimethyl-2-hexanone

d) 4,6-dimethyl-2-heptanone

e) 3,4-dimethyl-2-pentanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

207) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CHBrCH₃; then NaOH; then H₃O⁺; then heat

a) 3,5,5-trimethyl-2-hexanone

b) 2-butanone

c) 3,5-dimethyl-2-hexanone

d) 4,6-dimethyl-2-heptanone

e) 3,4-dimethyl-2-pentanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

208) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + CH₃I; then KO-t-Bu + (CH₃)₂CHBr; then NaOH; then H₃O⁺; then heat

a) 3,5,5-trimethyl-2-hexanone

b) 2-butanone

c) 3,5-dimethyl-2-hexanone

d) 4,6-dimethyl-2-heptanone

e) 3,4-dimethyl-2-pentanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

209) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + CH₃CH₂I; then KO-t-Bu + (CH₃)₃CCH₂CH₂Br; then NaOH; then H₃O⁺; then heat

a) 3-ethyl-6,6-dimethyl-2-heptanone

b) 3-ethyl-4,4-dimethyl-2-pentanone

c) 3-ethyl-6-methyl-2-heptanone

d) 4-ethyl-7-methyl-2-octanone

e) 3-ethyl-5-methyl-2-hexanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

210) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₃CCH₂Br; then KO-t-Bu + CH₃CH₂I; then NaOH; then H₃O⁺; then heat

a) 3-ethyl-6,6-dimethyl-2-heptanone

b) 3-ethyl-4,4-dimethyl-2-pentanone

c) 3-ethyl-6-methyl-2-heptanone

d) 4-ethyl-7-methyl-2-octanone

e) 3-ethyl-5-methyl-2-hexanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

211) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CH₂Br; then KO-t-Bu + CH₃CH₂I; then NaOH; then H₃O⁺; then heat

a) 3-ethyl-6,6-dimethyl-2-heptanone

b) 3-ethyl-4,4-dimethyl-2-pentanone

c) 3-ethyl-6-methyl-2-heptanone

d) 4-ethyl-7-methyl-2-octanone

e) 3-ethyl-5-methyl-2-hexanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

212) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + (CH₃)₂CHCH₂CH₂CHBrCH₂CH₃; then NaOH; then H₃O⁺; then heat

a) 3-ethyl-6,6-dimethyl-2-heptanone

b) 3-ethyl-4,4-dimethyl-2-pentanone

c) 3-ethyl-6-methyl-2-heptanone

d) 4-ethyl-7-methyl-2-octanone

e) 3-ethyl-5-methyl-2-hexanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

213) What is the major product of the following reaction sequence?

Ethyl acetoacetate + NaOC₂H₅ + CH₃CH₂I; then KO-t-Bu + (CH₃)₂CHCH₂Br; then NaOH; then H₃O⁺; then heat

a) 3-ethyl-6,6-dimethyl-2-heptanone

b) 3-ethyl-4,4-dimethyl-2-pentanone

c) 3-ethyl-6-methyl-2-heptanone

d) 4-ethyl-7-methyl-2-octanone

e) 3-ethyl-5-methyl-2-hexanone

Topic: Synthesis

Section: 18.6

Difficulty Level: Hard

214) Which of these amines will not form an enamine with aldehydes and ketones?

a) I

b) II

c) III

d) IV

e) Both III and IV

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Easy

215) Which of these amines will not form an enamine with aldehydes and ketones?

a) I

b) II

c) III

d) IV

e) I, II, and II

Topic: Enamine Chemistry

Section: 18.9

Difficulty Level: Easy