Final Exam Prep Chapter 20 Amines

Package title: Solomons Test Bank

Course Title: Solomons 12e

Chapter Number: 20

Question type: Multiple choice

1) Which of the following is a tertiary amine?

a) CH₃CH₂CH₂CH₂NH₂

b) CH₃CH₂NHCH₂CH(CH₃)₂

c) (CH₃CH₂)₂NCH₂CH(CH₃)₂

d) (CH₃CH₂)₄N⁺ OH^–

e) (CH₃CH₂)₃CNH₂

Topic: Nomenclature

Section: 20.1

Difficulty Level: Easy

2) What type of amine is pyridine?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Easy

3) What type of amine is N-methyl-2-methyl-3-hexanamine?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

4) What type of amine is quinoline?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

5) What type of amine is indole?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

6) Which is a correct common name for the following substance?

a) Ethylethylisobutylamine

b) Diethylisobutylamine

c) sec-Butyldiethylamine

d) Ethylethyl-sec-butylamine

e) 2-Diethylaminobutane

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

7) Which is a correct IUPAC name for the following substance?

a) N-Ethylhexanamine

b) N-Ethylcyclohexanamine

c) N-Cyclohexylethanamine

d) N-Ethylcyclopentanamine

e) N-Ethylaniline

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

8) Which is a correct IUPAC name for the following substance?

a) N-Cyclopentyl-N-methylcyclopentanamine

b) N-Cyclohexyl-N-methylcyclopentanamine

c) N-Cyclopentyl-N-methylcyclohexanamine

d) Dicyclopentylmethylamine

e) N-Pentyl-N-methylpentanamine

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

9) Which of these is properly termed a "quaternary ammonium salt"?

a) (CH₃)₃CCH₂CH₂NH₃⁺ Cl^–

b) (CH₃CH₂CH(CH₃)CH₂)₂NH₂⁺ Cl^–

c) (CH₃CH₂CH₂)₃NH⁺ Cl^–

d) (CH₃CH₂CH₂)₄N⁺ Cl^–

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Medium

10) The aromatic amine purine contains how many nitrogen atoms?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

11) The aromatic amine imidazole contains how many nitrogen atoms?

a) 1

b) 2

c) 3

d) 4

e) 5

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

12) Which of these is an acceptable alternative name to “(1-methylbutyl)amine”?

a) 2-Aminopentane

b) 2-Pentanamine

c) Isopentylamine

d) sec-Pentylamine

e) Both 2-aminopentane and 2-pentanamine

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

13) What type of amine is pyrrolidine?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

14) What type of amine is N-methylmorpholine?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

15) What type of amine is pyrrole?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

16) What type of amine is piperidine?

a) Primary

b) Secondary

c) Tertiary

d) Quaternary

e) None of these choices.

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

17) The correct structure of bicyclo[1.1.0]butan-2-amine is?

a) I

b) II

c) III

d) IV

e) V

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

18) The correct structure of bicyclo[1.1.0]butan-1-amine is?

a) I

b) II

c) III

d) IV

e) V

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

19) The correct structure of (S)-bicyclo[2.2.1]heptan-2-amine is?

a) I

b) II

c) III

d) IV

e) V

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

20) The correct structure of (S)-N-methylbicyclo[2.2.1]heptan-2-amine is?

a) I

b) II

c) III

d) IV

e) V

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

21) The correct structure of (R)-N-methylbicyclo[2.2.1]heptan-2-amine is?

a) I

b) II

c) III

d) IV

e) V

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

22) Which reagent could be used to separate a mixture of aniline and toluene?

a) KMnO₄ in H₂O

b) Dilute NaOH

c) Dilute NaHCO₃

d) Ag(NH₃)₂OH

e) Dilute HCl

Topic: Chemical Tests and Separations, Nomenclature

Section: 20.3

Difficulty Level: Medium

23) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) HONO, 0-5 °C then -naphthol

c) Dilute NaOH

d) C₆H₅SO₂Cl and OH^– in H₂O

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.8

Difficulty Level: Medium

24) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) Dilute NaHCO₃

c) Dilute NaOH

d) C₆H₅SO₂Cl/OH^–, then H₃O⁺

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

25) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) Tollens’ test

b) Dilute NaHCO₃

c) Hinsberg test

d) Iodoform test

e) None of these choices.

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

26) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) Dilute NaHCO₃

c) Dilute NaOH

d) C₆H₅SO₂Cl/OH^–, then H₃O⁺

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

27) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) Dilute NaHCO₃

c) Dilute NaOH

d) C₆H₅SO₂Cl/OH^–, then H₃O⁺

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

28) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) Dilute NaHCO₃

c) Dilute NaOH

d) C₆H₅SO₂Cl/OH^–, then H₃O⁺

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

29) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) Dilute NaHCO₃

c) Dilute NaOH

d) C₆H₅SO₂Cl/OH^–, then H₃O⁺

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

30) Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

a) AgNO₃ in H₂O

b) Dilute NaHCO₃

c) Dilute NaOH

d) C₆H₅SO₂Cl/OH^–, then H₃O⁺

e) Dilute HCl

Topic: Chemical Tests and Separations

Section: 20.9

Difficulty Level: Medium

31) Compound W has the molecular formula C₁₁H₁₇N. Treatment of W with benzenesulfonyl chloride in base gives no reaction. Acidification of the resulting mixture gives a clear solution. The ¹H NMR spectrum of W consists of:

triplet,  1.0

quartet,  2.5

singlet,  3.6 (2H)

multiplet,  7.3 (5H)

The most likely structure for W is:

a)

b)

c)

d)

e)

Topic: Chemical Tests, Separations and Analysis

Section: 20.9 and 20.11

Difficulty Level: Medium

32) Which reagent will distinguish between 2-amino-2,3-dimethylpentane and 1-amino-3-methyl-2-pentene?

a) HONO, 0-5 °C

b) C₆H₅SO₂Cl/OH^–, then H₃O⁺

c) NaOH

d) HCl

e) Br₂/CCl₄

Topic: Chemical Tests and Separations, Nomenclature

Section: 20.1

Difficulty Level: Hard

33) Which of these compounds is expected to possess the lowest boiling point?

a) CH₃CH₂CH₂CH₂CH₂NH₂

b) CH₃CH₂CH₂NHCH₂CH₃

c) (CH₃CH₂)₂NCH₃

d) (CH₃CH₂)₂CHOH

e) (CH₃)₃CCH₂NH₃⁺ Cl^-

Topic: Reactive Intermediates and General Considerations

Section: 20.2

Difficulty Level: Easy

34) What is the basis for the successful resolution of racemic C₆H₅CHOHCO₂H through use of the chiral amine, C₆H₅CH(NH₂)CH₃?

a) One enantiomer is more soluble than the other.

b) The racemic mixture is converted into a single isomer in the basic solvent.

c) The diastereomeric salts formed have different solubilities.

d) The diastereomeric salts have different boiling points.

e) The diastereomeric salts have different melting points.

Topic: Reactive Intermediates and General Considerations

Section: 20.3

Difficulty Level: Easy

35) This type of compound is the only one of these which can be converted by reduction into a 1, 2 or 3 amine, according to its particular structure:

a) Nitrile

b) Oxime

c) Azide

d) Amide

e) Nitroalkane

Topic: Reactive Intermediates and General Considerations

Section: 20.4

Difficulty Level: Easy

36) When the process ArNH₂  ArY is carried out via an intermediate diazonium salt, this salt is isolated only in the case in which Y is which of these groups?

a) -F

b) -Cl

c) -Br

d) -I

e) -CN

Topic: Reactive Intermediates and General Considerations

Section: 20.6

Difficulty Level: Easy

37) Which of these alkyl halides cannot be used effectively in a Gabriel amine synthesis?

a) 1-bromopentane

b) 1-bromo-3-methylbutane

c) 2-bromo-3-methylpentane

d) 1-bromo-2,3-dimethylbutane

e) 2-bromo-2,3-dimethylbutane

Topic: Reactive Intermediates and General Considerations

Section: 20.6

Difficulty Level: Easy

38) Which is not an intermediate in the Hofmann degradation reaction?

a) RN=C=O

b)

c)

d)

e)

Topic: Reactive Intermediates and General Considerations

Section: 20.4

Difficulty Level: Medium

39) The reaction of which of these compounds with nitrous acid results in a stable N-nitroso compound?

a) C₆H₅NH₂

b) C₆H₅N(CH₃)₂

c) CH₃CH₂CH₂CH₂CH₂NH₂

d) C₆H₅NHCH₃

e) CH₃CH₂CONH₂

Topic: Reactive Intermediates and General Considerations

Section: 20.6

Difficulty Level: Hard

40) Which of the following compounds would be the strongest base?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

41) Which of the following compounds would be the weakest base?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

42) Which of the following bases has a conjugate acid with the largest pK_a?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

43) Which of the following bases has a conjugate acid with the smallest pK_a?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

44) Which of the following compounds would be the strongest base?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

45) Arrange the following amines in order of increasing basicity (least to most) in aqueous solution:

a) IV < II < I < III

b) III < II < IV < I

c) III < I < II < IV

d) II < III < I < IV

e) Cannot be determined from information given

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

46) Arrange the following amines in order of decreasing basicity (most to least) in aqueous solution:

a) IV > II > I > III

b) III > II > IV > I

c) III > I > II > IV

d) II > III > I > IV

e) Cannot be determined from information given

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

47) Which of the following bases has a conjugate acid with the smallest pK_a?

a) I

b) II

c) III

d) IV

e) Cannot be determined from information given

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

48) Arrange the following compounds in order of increasing basicity (least to most) in aqueous solution:

a) IV < II < I < III

b) III < II < IV < I

c) II < I < III < IV

d) II < III < I < IV

e) Cannot be determined from information given

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

49) Arrange the following compounds in order of increasing basicity (least to most) in aqueous solution:

a) IV < II < I < III

b) III < II < IV < I

c) II < I < III < IV

d) II < III < I < IV

e) Cannot be determined from information given

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

50) Which of the following aryl amines is the strongest base?

a) Aniline

b) p-Trimethylammonium aniline

c) p-Methoxyaniline

d) p-Trifluoromethylaniline

e) p-Chloroaniline

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

51) Which of the following aryl amines is the weakest base?

a) Aniline

b) p-Trimethylammonium aniline

c) p-Methoxyaniline

d) p-Trifluoromethylaniline

e) p-Chloroaniline

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

52) In aqueous solution, which of the following bases has the conjugate acid that possesses the smallest value for pK_a?

a) C₆H₅NH₂

b) NH₃

c) (CH₃CH₂)₃N

d) (CH₃CH₂)₂NH

e) CH₃CH₂CH₂NH₂

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

53) Which of these is the strongest acid?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

54) Which of these is the weakest acid?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

55) Which of these would be predicted to have the smallest pK_a?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

56) Which of these would be predicted to have the largest pK_a?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

57) Which of these is the strongest acid?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.4

Difficulty Level: Medium

58) Which of these compounds is soluble in dilute sodium hydroxide solution?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.4

Difficulty Level: Medium

59) Which would be the weakest base?

a) p-Methylaniline

b) p-Methoxyaniline

c) Hexylamine

d) p-Nitroaniline

e) Dipropylamine

Topic: Basicity

Section: 20.3

Difficulty Level: Hard

60) Which of the following bases has a conjugate acid with the smallest pK_a?

a) p-Methylaniline

b) p-Methoxyaniline

c) Hexylamine

d) p-Nitroaniline

e) Dipropylamine

Topic: Basicity

Section: 20.3

Difficulty Level: Hard

61) Which of these could be resolved into separate enantiomers?

a) 4-Methyl-1-pentanamine

b) 4-Methyl-2-pentanamine

c) N-Methyl-1-butanamine

d) N,N-Dimethyl-1-propanamine

e) N-Butyltrimethylammonium bromide

Topic: Chemical Tests, Separations and Analysis

Section: 20.3

Difficulty Level: Hard

62) Consider the synthesis below. What is reagent A?

a) Br₂, FeBr₃

b) Fe, HCl; then OH^–

c) NH₂Cl, AlCl₃

d) H₃PO₂

e) LiNH₂

Topic: Synthesis

Section: 20.4

Difficulty Level: Easy

63) Consider the synthesis below. What is compound B?

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 20.4

Difficulty Level: Easy

64) Consider the synthesis below. What is reagent C?

a) excess Br₂, H₂O

b) Fe, HCl; then OH^–

c) NH₂Cl, AlCl₃

d) CuBr

e) HNO₃, H₂SO₄, Fe

Topic: Synthesis

Section: 20.4

Difficulty Level: Easy

65) What reagent can effect the following transformation?

a) Fe/HCl; then OH^–

b) NH₂Cl

c) H₃PO₂

d) CuCN

e) HONO; then NH₃

Topic: Synthesis

Section: 20.4

Difficulty Level: Easy

66) What reagent can effect the following transformation?

a) Sn/HCl; then OH^–

b) NH₂Cl

c) H₃PO₂

d) CuCN

e) HONO; then NH₃

Topic: Synthesis

Section: 20.4

Difficulty Level: Easy

67) Consider the synthesis below. What is reagent “Z”?

a) CuCl

b) CuCl₂

c) NaCl

d) KCl

e) HCl/heat

Topic: Synthesis

Section: 20.7

Difficulty Level: Easy

68) Consider the synthesis below. What is reagent A?

a) H₃PO₂

b) HCN

c) P₄O₁₀

d) CuCN

e) CuCl₂

Topic: Synthesis

Section: 20.7

Difficulty Level: Easy

69) Consider the synthesis below. What is reagent “Y”?

a) Br₂/FeBr₃

b) CuBr

c) CuBr₂

d) H₃PO₂/H₂O

e) H₃PO₄

Topic: Synthesis

Section: 20.7

Difficulty Level: Easy

70) Which of the following can be used to prepare 2-aminopentane (pure)?

a) I

b) II

c) III

d) I and II

e) II and III

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

71) Which of the following can be used to prepare allylamine (pure)?

a) I

b) II

c) III

d) I and II

e) II and III

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

72) Which of the following can be used to prepare benzylamine (pure)?

a) I

b) II

c) III

d) I and II

e) II and III

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

73) Which is the best method to prepare ?

a)

b)

c)

d)

e)

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

74) Which is the best method to prepare 1-phenylethanamine?

a)

b)

c)

d)

e)

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

75) Which is the best method to prepare 1-phenylethanamine?

a)

b)

c)

d)

e)

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

76) Identify the best method(s) to prepare .

a)

b)

c)

d) and

e) and

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

77) Identify the best method(s) to prepare N-methylphenylmethanamine.

a)

b)

c)

d) and

e) and

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

78) Identify the best method(s) to prepare N-methylphenylmethanamine.

a)

b)

c)

d) and

e) and

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

79) Identify the best method(s) to prepare N-methylphenylmethanamine.

a)

b)

c)

d) and

e) and

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

80) Which of the following reactions would yield C₆H₅CH₂NH₂?

a)

b)

c)

d) All of these choices.

e) Two of these choices.

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

81) Which of the following reactions would yield benzylamine?

a)

b)

c)

d) All of these choices.

e) Two of these choices.

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

82) The overall conversion RBr  RCH₂NH₂ can be accomplished by successive application of which of these sets of reagents?

a) Mg, ether; then NH₃

b) NaN₃; then LiAlH₄, ether

c) NaCN; then LiAlH₄, ether

d) H₂C=O; then NH₃

e) H₂NOH; then LiAlH₄, ether

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

83) Which combination of reactants will not produce ?

a)

b)

c)

d)

e)

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

84) Which of the following might be used to synthesize m-bromoaniline?

a)

b)

c)

d) and

e) and

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

85) What is the final product in the Curtius rearrangement of the acyl azide formed from butanoyl chloride?

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

86) How could one carry out this synthesis?

a) SOCl₂; then NH₃; then H₃PO₂

b) CH₃Li, ether; then NH₃, H₂, Ni

c) SOCl₂; then NH₃; then Br₂, NaOH

d) PCl₅; then NH₃; then HCl, NaNO₂, 0-5 °C

e) PCl₅; then CH₃NH₂; then KMnO₄, OH^–, heat

Topic: Synthesis

Section: 17.8 and 20.4

Difficulty Level: Medium

87) How could one carry out this synthesis?

a) SOCl₂; then NH₃; then H₃PO₂

b) CH₃Li, ether; then NH₃, H₂, Ni

c) SOCl₂; then NaN₃; then heat

d) PCl₅; then NH₃; then HCl, NaNO₂, 0-5 °C

e) PCl₅; then CH₃NH₂; then KMnO₄, OH^–, heat

Topic: Synthesis

Section: 17.8 and 20.4

Difficulty Level: Medium

88) Which of the following reaction sequences would yield aniline?

a)

b)

c)

d) All of these choices.

e) Two of these choices.

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

89) The best synthesis of 3,5-dibromotoluene would be:

a) Toluene, Br₂, Fe and heat

b) p-CH₃C₆H₄NH₂, Br₂, H₂O; then HONO, 0-5 °C; then H₃PO₂

c) Toluene, fuming HNO₃, H₂SO₄; then NH₃, H₂S; then HONO, 0-5 °C; then CuBr

d) m-Dibromobenzene, CH₃Cl, AlCl₃, heat

e) m-Bromotoluene, HNO₃, H₂SO₄; then NH₃, H₂S; then HONO, 0-5 °C; then CuBr

Topic: Synthesis

Section: 20.7

Difficulty Level: Medium

90) How would one carry out the following transformation?

a) NaNO₂, HCl, 0-5 C; then HNO₃

b) NaNO₂, HCl, 0-5 C; then H₃PO₂

c) NaNO₂, HCl, 0-5 C; then H₂,Ni

d) C₆H₅SO₂Cl, OH^–; then HCl

e) NaH, DMSO

Topic: Synthesis

Section: 20.7

Difficulty Level: Medium

91) The best synthesis of m-dibromobenzene would be:

a) Benzene, Br₂, FeBr₃, heat

b) Aniline, Br₂, H₂O; then HONO, 0-5 °C; then CuBr

c) Nitrobenzene, HNO₃, H₂SO₄, heat; then Fe/HCl (excess); then 2 HONO, 0-5 °C; then 2 CuBr

d) Bromobenzene, HNO₃, H₂SO₄; then Fe, HCl, C₂H₅OH, reflux; then HONO, 0-5 °C; then CuBr

e) Two of these choices.

Topic: Synthesis

Section: 20.4, and 20.7

Difficulty Level: Medium

92) Which is the best preparation of benzonitrile, C₆H₅CN, from benzene?

a) HNO₃/H₂SO₄; then Fe/HCl; then HONO, 0-5 °C; then CuCN

b) CH₃I, AlCl₃; then hot KMnO₄; then H₃O⁺; then SOCl₂; then NH₃; then NaOH + Cl₂

c) CH₃I, AlCl₃; then Br₂, h; then KCN

d) Br₂, Fe; then KCN

e) CH₃I, AlCl₃; then Br₂ (2 eq.), h; then hot NaOH; then HCN

Topic: Synthesis

Section: 20.4 and 20.7

Difficulty Level: Medium

93) What is the principal product when aniline is treated with sodium nitrite and hydrochloric acid at 0-5 C and this mixture is added to p-ethylphenol?

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 20.8

Difficulty Level: Medium

94) What is the chief product of the Hofmann elimination reaction applied to the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 20.12

Difficulty Level: Medium

95) What is the chief product of the Hofmann elimination reaction applied to the compound shown?

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 20.12

Difficulty Level: Medium

96) Which is the best method to prepare 1-phenylethanamine ?

a)

b)

c)

d)

e)

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

97) Which is the best method to prepare 1-phenylethanamine ?

a)

b)

c)

d)

e)

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

98) Which of the following reactions would yield benzylamine?

a)

b)

c)

d) All of these choices.

e) Two of these choices.

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

99) Which of the following reactions would yield benzylamine?

a)

b)

c)

d) All of these choices.

e) Two of these choices.

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

100) Which of the following might be used to synthesize m-bromoaniline?

a)

b)

c)

d) and

e) and

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

101) Your task is to convert o-xylene into o-diaminobenzene. Which sequence of reagents constitutes the best method?

a) NaNH₂ and heat

b) NBS/CCl₄; then NH₃; then Br₂/OH^–

c) KMnO₄, OH^–, heat; then H₃O⁺; then PCl₅; then NH₃, then Br₂/OH^–

d) KMnO₄, OH^–, heat; then H₃O⁺; then SOCl₂; then NH₃; then LiAlH₄; then Br₂/OH^–

e) KMnO₄, OH^–, heat; then H₃O⁺; then NH₃ with H₂/Ni

Topic: Synthesis, Nomenclature

Section: 17.8 and 20.4

Difficulty Level: Hard

102) What is the product of the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Synthesis

Section: 20.7

Difficulty Level: Hard

103) What would be the product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Easy

104) What would be the product of the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Easy

105) When an equimolar mixture of ammonia and butyl bromide reacts, which of these products will form?

a) Butylamine

b) Dibutylamine

c) Tributylamine

d) Tetrabutylammonium bromide

e) All of these choices.

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

106) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Medium

113) Which product could not be formed during the following reaction?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.6

Difficulty Level: Medium

114) Identify the compound (Z) formed when aniline is subjected to the following series of reactions:

i.) NaNO₂, H₂SO₄, 0-5 ^oC; ii.) Cu₂O, Cu(NO₃)₂, H₂O

a) C₆H₅NH₂

b) C₆H₅Cl

c) C₆H₅OH

d) C₆H₆

e) None of these choices.

Topic: Reaction Products

Section: 20.7

Difficulty Level: Medium

115) Which is the major product of the following reaction?

2

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.7

Difficulty Level: Medium

116) Which is the major product of the following reaction?

2

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.7

Difficulty Level: Medium

117) What final product is expected from the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

118) What final product is expected from the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

119) What compound is likely to be obtained via the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

120) What compound is likely to be obtained via the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

121) What compound is likely to be obtained via the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

122) What compound is likely to be obtained via the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

123) What compound is likely to be obtained via the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

125) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Medium

126) Which is the major product of the following reaction?

2

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.8

Difficulty Level: Medium

127) Which is the major product of the following reaction?

2

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.8

Difficulty Level: Medium

128) Which is the major product of the following reaction?

2

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.8

Difficulty Level: Medium

129) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) Two of these choices.

Topic: Reaction Products

Section: 20.12

Difficulty Level: Medium

130) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

131) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Medium

132) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

133) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Medium

134) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

135) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Medium

136) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

137) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Medium

138) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Product

Section: 20.12

Difficulty Level: Medium

139) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Product

Section: 20.12

Difficulty Level: Medium

140) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Product

Section: 20.12

Difficulty Level: Medium

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Hard

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Hard

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Hard

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

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Hard

145) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.4

Difficulty Level: Hard

146) What final product is expected when toluene is subjected to the following reaction sequence?

i) KMnO₄, NaOH; ii) H₃O⁺; iii) SOCl₂; iv) NaN₃; v) heat, H₂O

a) C₆H₅CONH₂

b) C₆H₅CH₂NH₂

c) p-CH₃C₆H₄SO₂NH₂

d) p-CH₃C₆H₄NH₂

e) C₆H₅NH₂

Topic: Reaction Products

Section: 20.4

Difficulty Level: Hard

147) What final product is expected when toluene is subjected to the following reaction sequence?

i) KMnO₄, NaOH; ii) H₃O⁺ (product = C₇H₆O₂); iii) SOCl₂;

iv) NH₃ (product = C₇H₇NO); v) Br₂, NaOH

a) C₆H₅CONH₂

b) C₆H₅CH₂NH₂

c) p-CH₃C₆H₄SO₂NH₂

d) p-CH₃C₆H₄NH₂

e) C₆H₅NH₂

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

148) What is the final product of the reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

149) What is the final product of the reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

150) What is the final product of the reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

151) What is the final product of the reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

152) What is the final product of the reaction sequence:

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

153) What is the final product of the reaction sequence:

a)

b)

c)

d)

e)

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

154) What would be the product of the following reaction sequence?

a) p-bromobenzamide

b) p-bromobenzaldehyde oxime

c) p-bromobenzenesulfonamide

d) p-bromoaniline

e) 4-bromo-3-chlorobenzoic acid

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

155) What would be the product of the following reaction sequence?

a) p-bromobenzamide

b) p-bromobenzaldehyde oxime

c) p-bromobenzenesulfonamide

d) p-bromoaniline

e) 4-bromo-3-chlorobenzoic acid

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

156) What would be the product of the following reaction sequence?

a) p-bromobenzamide

b) p-bromobenzaldehyde oxime

c) p-bromobenzenesulfonamide

d) p-bromoaniline

e) 4-bromo-3-chlorobenzoic acid

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

157) What would be the product of the following reaction sequence?

a) p-bromobenzamide

b) p-bromobenzaldehyde oxime

c) p-bromobenzenesulfonamide

d) p-bromoaniline

e) 4-bromo-3-chlorobenzoic acid

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

158) What would be the product of the following reaction sequence?

a) p-bromobenzamide

b) p-bromobenzaldehyde oxime

c) p-bromobenzenesulfonamide

d) p-bromoaniline

e) 4-bromo-3-chlorobenzoic acid

Topic: Reaction Products

Section: 17.8 and 20.4

Difficulty Level: Hard

159) What is the final product?

a) 2-Bromo-4-methylaniline

b) 2,6-Dibromo-4-methylaniline

c) 2,6-Dibromo-4-methylphenol

d) 2,4-Dibromophenol

e) 3,5-Dibromotoluene

Topic: Reaction Products

Section: 20.4 and 20.7

Difficulty Level: Hard

160) Which is the major product of the following reaction?

2

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.8

Difficulty Level: Hard

161) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) Two of these choices.

Topic: Reaction Products

Section: 20.12

Difficulty Level: Hard

162) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Hard

163) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Hard

164) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Hard

165) What would be the product of the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Products

Section: 20.12

Difficulty Level: Hard

166) What is the chief alkene product when butylethylmethylpropylammonium hydroxide is heated to 150C?

a) CH₂=CH₂

b) CH₃CH=CH₂

c) CH₃CH₂CH=CH₂

d) (E)-CH₃CH=CHCH₃

e) (Z)-CH₃CH=CHCH₃

Topic: Reaction Products

Section: 20.12

Difficulty Level: Hard

167) What is the final product from the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

168) What is the final product from the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

169) What is the final product from the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

170) What is the final product from the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

171) What is the final product from the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

172) What is the final product from the following reaction sequence:

a) I

b) II

c) III

d) IV

e) V

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

173) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

174) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

175) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

176) What would be the reactant in the following reaction sequence?

a) I

b) II

c) III

d) IV

e) V

Topic: Predict Reactant

Section: 20.12

Difficulty Level: Medium

Question type: Essay

177) Draw the structure corresponding to the following name:

(4Z,3S)-2,4,7-trimethyl-3-amino-4-octene

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

178) Draw the structure corresponding to the following name:

(3S,6R)-6-(2,4-dinitrophenyl)-3-amino-1-heptyne

Topic: Nomenclature

Section: 20.1

Difficulty Level: Hard

179) If the three alkyl groups of a tertiary amine are all different, the amine will be chiral. In practice, however, it is virtually impossible to separate the two enantiomers, because they interconvert rapidly through a process called ___.

Topic: Stereochemistry

Section: 20.2

Difficulty Level: Easy

180) Amines are known to rapidly undergo pyramidal inversion at ordinary temperatures, preventing the resolution of enantiomeric forms when the amine is a chirality center. The proposed transition state of the inversion process is shown below. Using an orbital diagram, illustrate the hybridization at nitrogen for this proposed transition state.

sp³ sp² p

Topic: Amine Structure, Hybridization at Nitrogen

Section: 20.2

Difficulty Level: Hard

181) In solution, two factors affect the relative basicity of amines. These factors are: ___.

Topic: Relative Basicity

Section: 20.3

Difficulty Level: Easy

182) Arylamines are less basic than alkylamines because of ___.

Topic: Relative Basicity

Section: 20.3

Difficulty Level: Easy

183) Explain how an enantiomerically pure amine can be used to resolve racemic forms of acidic compounds.

Topic: Relative Basicity

Section: 20.3

Difficulty Level: Medium

184) Explain why cyclohexylamine is a stronger base than aniline.

In aniline, the electron pair on N is delocalized over the aromatic ring through resonance: this has the effect of decreasing the electron density at the nitrogen atom, relative to cyclohexylamine, in which no such resonance delocalization can occur, leading to lower base strength for aniline.

In cyclohexylamine, the N atom is attached to an sp³ carbon, while in aniline the N atom is attached to an sp² carbon: an sp² carbon typically exerts a stronger electron-withdrawing effect, effectively decreasing the electron density on the nitrogen atom, resulting in weaker base strength.

Topic: Relative Base Strength

Section: 20.3

Difficulty Level: Medium

185) Using resonance theory, explain why guanidine is one of the strongest organic bases.

The protonated form (conjugate acid) of guanidine is stabilized through three equivalent resonance structures (shown), making it a very weak acid or the conjugate base a strong base.

Topic: Amine Basicity

Section: 20.3

Difficulty Level: Medium

186) List the following compounds in order of increasing basicity (least to most), and explain your reasoning.

Reasoning – basicity follows the order of decreasing electronegativity of the nitrogen atom. Electronegativity of nitrogen is a function of hybridization, with the more s-character in the hybrid orbital, the higher the electronegativity. In I the hybridization of nitrogen is sp, while in II it is sp² and in III, sp³.

Topic: Amine Basicity and Orbital Hybridization

Section: 3.8 and 20.3

Difficulty Level: Hard

187) List the following compounds in order of increasing electronegativity (least to most) of the nitrogen atom, and explain your reasoning.

Reasoning – Electronegativity of nitrogen is a function of hybridization, with the more s-character in the hybrid orbital, the higher the electronegativity. In I the hybridization of nitrogen is sp, while in II it is sp² and in III, sp³.

Topic: Amine Basicity and Orbital Hybridization

Section: 3.8 and 20.3

Difficulty Level: Hard

188) Outline the steps involved in the Gabriel synthesis of 3-amino-2-methylpentane.

3-amino-2-methylpentane

Topic: Multistep Reaction Sequence, Nomenclature

Section: 20.4

Difficulty Level: Medium

189) Outline the steps involved in the Gabriel synthesis of allyl amine.

allyl amine

Topic: Multistep Reaction Sequence, Nomenclature

Section: 20.4

Difficulty Level: Medium

190) Outline the steps involved in the Gabriel synthesis of allylamine.

benzylamine

Topic: Multistep Reaction Sequence, Nomenclature

Section: 20.4

Difficulty Level: Medium

191) What final product is likely when acetophenone is subjected to the following reaction sequence? Give structural details of all significant intermediates.

i) Br₂, FeBr₃; ii) CH₃CH₂CH₂NH₂; ii.) NaBH₃CN

Topic: Multistep Reaction Sequence, Nomenclature

Section: 20.4

Difficulty Level: Medium

192) What final product is likely when cyclohexene is subjected to the following reaction sequence? Give structural details of all significant intermediates.

i) H₃O⁺, H₂O; ii) PCC; iii) (CH₃)₂NH; iv) NaBH₃CN

Topic: Multistep Reaction Sequence

Section: 20.4

Difficulty Level: Hard

193) What final product is likely when cyclohexene is subjected to the following reaction sequence? Give structural details of all significant intermediates.

i) H₃O⁺, H₂O; ii) PCC; iii) pyrrolidine; iv) NaBH₃CN

Topic: Multistep Reaction Sequence

Section: 20.4

Difficulty Level: Hard

194) What final product is likely when cyclohexene is subjected to the following reaction sequence? Give structural details of all significant intermediates.

i) H₃O⁺, H₂O; ii) PCC; iii) piperidine; iv) NaBH₃CN

Topic: Multistep Reaction Sequence

Section: 20.4

Difficulty Level: Hard

195) What final product is likely when cyclohexene is subjected to the following reaction sequence? Give structural details of all significant intermediates.

i) H₃O⁺, H₂O; ii) PCC; iii) morpholine; iv) NaBH₃CN

Topic: Multistep Reaction Sequence

Section: 20.4

Difficulty Level: Hard

196) There are two very versatile synthetic methods that can be used to synthesize primary, secondary, and tertiary amines. These methods are: ___.

Topic: General, Synthesis of Amines

Section: 20.4

Difficulty Level: Medium

197) Propose structures corresponding to each of the molecular formulas given in the following reaction sequence:

Topic: Reaction Sequence

Section: 20.4

Difficulty Level: Medium

198) While primary amines react with nitrous acid to generate diazonium salts, secondary amines react with nitrous acid to produce ___.

Topic: Chemical Analysis

Section: 20.6

Difficulty Level: Medium

199) Outline the steps involved in the synthesis of 3-chloro-4-fluoroacetophenone from 4-aminoacetophenone.

Topic: Synthetic Strategy and Nomenclature

Section: 20.7

Difficulty Level: Medium

200) What is the principal product when p-toluidine is treated with sodium nitrite and hydrochloric acid at 0-5C and this mixture is added to o-ethylphenol?

Topic: Synthetic Strategy and Nomenclature

Section: 20.8

Difficulty Level: Medium

201) Outline the steps involved in the synthesis of 4-bromo-3-nitro-phenol from 4-bromobenzoic acid

vi) Cu₂O, Cu(NO₃)₂, H₂O

Topic: Synthetic Strategy and Nomenclature

Section: 20.7

Difficulty Level: Hard

202) Azo compounds are usually intensely colored because ___.

Topic: UV-Vis Absorption

Section: 20.8

Difficulty Level: Medium

203) You have just completed an experiment involving the reduction of m-nitrobenzoic acid with Fe/HCl. In order to determine if your reaction has worked as planned, you have obtained the ¹H NMR of your crude product. What will you scrutinize the spectrum for, in order to help you make this assessment?

Topic: Product Analysis by NMR

Section: 20.4 and 20.11

Difficulty Level: Medium

204) Eliminations that follow the Hofmann Rule tend to give the ___ alkene as the major product.

Topic: Hofmann Elimination

Section: 20.12

Difficulty Level: Easy

205) What reactant must be used to produce the product shown:

Topic: Synthetic Strategy

Section: 20.12

Difficulty Level: Medium

206) Before modern spectroscopic methods were developed, structures of many complex amines were elucidated by examining the products obtained during Hofmann elimination of their quaternary ammonium hydroxides. The typical procedure involved the following steps, repeated as necessary, depending on whether the amine was primary, secondary or tertiary, until the final product was nitrogen-free: i) CH₃I (excess); ii) Ag₂O, H₂O; iii) heat. What product(s) is (are) likely to be formed if 3,4-dimethylpiperidine is subjected to the above procedure?

Topic: Exhaustive Methylation, Hofmann Degradation, Nomenclature

Section: 20.12

Difficulty Level: Hard

207) In the following sequence fill in the needed reagents.

Topic: Reaction Sequence

Section: 20.4 and 20.12

Difficulty Level: Hard

208) Which of the following is a secondary amine?

a) CH₃CH₂CH₂CH₂NH₂

b) CH₃CH₂NHCH₂CH(CH₃)₂

c) (CH₃CH₂)₂NCH₂CH(CH₃)₂

d) (CH₃CH₂)₄N⁺ OH^–

e) (CH₃CH₂)₃CNH₂

Topic: Nomenclature

Section: 20.1

Difficulty Level: Easy

209) Which of the following is a primary amine?

a) CH₃CH₂CH₂CH₂NH₂

b) CH₃CH₂NHCH₂CH(CH₃)₂

c) (CH₃CH₂)₂NCH₂CH(CH₃)₂

d) (CH₃CH₂)₄N⁺ OH^–

e) (CH₃CH₂)₃CNCH₃

Topic: Nomenclature

Section: 20.1

Difficulty Level: Easy

210) Which of these compounds is expected to possess the highest boiling point?

a) CH₃CH₂CH₂CH₂CH₂NH₂

b) CH₃CH₂CH₂NHCH₂CH₃

c) (CH₃CH₂)₂NCH₃

d) (CH₃CH₂)₂CHOH

e) (CH₃)₃CCH₂NH₃⁺ Cl^-

Topic: Reactive Intermediates and General Considerations

Section: 20.2

Difficulty Level: Easy

211) Which of the following compounds would be the weakest base?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.3

Difficulty Level: Medium

212) Which of these is the strongest base?

a) I

b) II

c) III

d) IV

e) V

Topic: Basicity

Section: 20.4

Difficulty Level: Medium

213) Which of the following bases has a conjugate acid with the largest pK_a?

a) p-Methylaniline

b) p-Methoxyaniline

c) Hexylamine

d) p-Nitroaniline

e) aniline

Topic: Basicity

Section: 20.3

Difficulty Level: Hard

214) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N,N-tetra(1-phenylethyl)ammonium bromide

c) N-methyl-benzylamine

d) benzylamine

e) N-methylaniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

215) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N,N-tetra(1-phenylethyl)ammonium bromide

c) N-methyl-benzylamine

d) benzylamine

e) N-methylaniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

216) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N,N-tetra(1-phenylethyl)ammonium bromide

c) N-methyl-benzylamine

d) benzylamine

e) N-methylaniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

217) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N,N-tetra(1-phenylethyl)ammonium bromide

c) N-methyl-benzylamine

d) benzylamine

e) N-methylaniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

218) What is the major product of the following reaction?

a) N-methyl-2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

219) What is the major product of the following reaction?

a) N-methyl-2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

220) What is the major product of the following reaction?

a) N-methyl-2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

221) What is the major product of the following reaction?

a) N-methyl-2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

222) What is the major product of the following reaction?

a) 2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

223) What is the major product of the following reaction?

a) 2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

224) What is the major product of the following reaction?

a) 2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

225) What is the major product of the following reaction?

a) N-ethylpropanamine

b) N-ethylethylamine

c) N-propylpropanamine

d) N-methylpropanamine

e) N-methylethylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

226) What is the major product of the following reaction?

a) N-ethylpropanamine

b) N-ethylethylamine

c) N-propylpropanamine

d) N-methylpropanamine

e) N-methylethylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

227) What is the major product of the following reaction?

a) N-ethylpropanamine

b) N-ethylethylamine

c) N-propylpropanamine

d) N-methylpropanamine

e) N-methylethylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

228) What is the major product of the following reaction?

a) 2,4,6-tribromoaniline

b) 2,4,6-tribromo-1-nitroaniline

c) 3-bromoaniline

d) 2-bromoaniline

e) aniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

229) What is the major product of the following reaction?

a) 2,4,6-tribromoaniline

b) 2,4,6-tribromo-1-nitroaniline

c) 3-bromoaniline

d) 2-bromoaniline

e) aniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

230) What is the major product of the following reaction?

a) 2,4,6-trichloroaniline

b) 2,4,6-trichloro-1-nitroaniline

c) 3-chloroaniline

d) 2-chloroaniline

e) aniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

231) What is the major product of the following reaction?

a) 2,4,6-trichloroaniline

b) 2,4,6-trichloro-1-nitroaniline

c) 3-chloroaniline

d) 2-chloroaniline

e) aniline

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium

232) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

233) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N,N-tetra(1-phenylethyl)ammonium bromide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

234) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

235) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

236) What is the major product of the following reaction?

a) 1-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Hard

237) What is the major product of the following reaction?

a) 2-phenylethanamine

b) N,N,N-trimethyl-2-phenylethanammonium iodide

c) N-benzyl-N,N-dimethylamine

d) N-benzyl-N-methylamine

e) benzylamine

Topic: Synthesis

Section: 20.4

Difficulty Level: Medium