Exam Prep Smith Amines Ch.23

Organic Chemistry, 6e (Smith)

Chapter 23 Amines

1) Which of the following amines are classified as primary (1°) amines?

A) I

B) II

C) III

D) I and II

2) Which of the following amines are classified as secondary (2°) amines?

A) I

B) II

C) III

D) I and II

3) Which of the following amines are classified as tertiary (3°) amines?

A) I

B) II

C) III

D) IV

4) What is the approximate bond angle of the substituents around a nitrogen atom in amines?

A) 90°

B) 109.5°

C) 120°

D) 180°

5) Although an amine nitrogen atom containing an electron pair and bonded to three different groups is technically a stereogenic center, the chirality of the amine nitrogen is often ignored. Why is that?

A) Because four bonds are needed to define a stereogenic center

B) Because chirality only exists with the tetrahedral carbon atoms

C) Because there is usually slow interconversion between the two isomeric forms at room temperature

D) Because there is usually rapid interconversion between the two isomeric forms at room temperature

6) Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?

A) Because there is rapid interconversion between the two isomeric forms at room temperature

B) Because interconversion cannot occur between the two isomeric forms at room temperature

C) Because the compound would be a meso compound

D) Because the compound would be a racemic mixture

7) What is the common name of the following compound?

A) Isopropylamine

B) Sec-butylamine

C) 2-Methyl-1-propanamine

D) Isobutylamine

8) What is the common name of the following compound?

A) isopropylamine

B) sec-butylamine

C) isobutylamine

D) tert-butylamine

9) What is the common name of the following compound?

A) isopropylamine

B) 2-methyl-2-propanamine

C) tert-butylamine

D) isobutylamine

10) What is the common name of the following compound?

A) diisopropylamine

B) dipropylamine

C) diisopropanamine

D) dibutylamine

11) What is the common name of the following compound?

A) dimethylisobutylamine

B) butyldimethylamine

C) N,N-dimethylbutanamine

D) sec-butyldimethylamine

12) What is the IUPAC name of the following compound?

A) N-propylhexanamine

B) N-propylaniline

C) N-ethylcyclohexylamine

D) N-propylcyclohexanamine

13) What is the IUPAC name of the following compound?

A) N-ethyl-N-methylpentylamine

B) N-ethyl-N-methyl-1-pentanamine

C) N-methyl-3-octanamine

D) N-ethyl-2-heptanamine

14) What is the IUPAC name of the following compound?

A) 3-methyl-1-hexanamine

B) 4-methyl-1-hexylamine

C) 4-methyl-1-hexanamine

D) 3-methyl-6-hexylamine

15) What is the IUPAC name of the following compound?

A) N-ethyl-N-methylcyclopentanamine

B) N-cyclopentyl-N-methylethanamine

C) N-methyl-N-ethylcyclopentylamine

D) N-ethyl-N-methylpentanamine

16) What is the IUPAC name of the following compound?

A) 1-methyl-N-propyl-1-propanamine

B) 4-methyl-4-heptanamine

C) 2-propyl-3-hexanamine

D) N-propyl-2-pentanamine

17) What is the IUPAC name of the following compound?

A) (S)-methyl-4-hexanamine

B) (S)-5-methyl-3-hexanamine

C) (R)-2-methyl-4-hexanamine

D) (R)-5-methyl-3-hexanamine

18) What is the IUPAC name of the following compound?

A) (Z)-4-hexen-1-amine

B) (E)-4-hexen-1-amine

C) (E)-2-hexen-6-amine

D) (Z)-2-hexen-6-amine

19) What is the correct assignment of the names of the following aromatic amines?

A) I = pyrrolidine; II = pyrimidine; III = aniline

B) I = pyrrole; II = pyrimidine; III = anisole

C) I = pyrrolidine; II = pyridine; III =aniline

D) I = pyrrole; II = pyridine; III = aniline

20) Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > II > III

B) I > III > II

C) III > I > II

D) III > II > I

21) Arrange the following compounds in order of increasing boiling point, putting the compound with the least boiling point first.

A) I < II < III

B) II < I < III

C) I < III < II

D) II < III < I

22) Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first.

A) I > II > III

B) II > I > III

C) III > I > II

D) II > III > I

23) The mass spectrum of an amine shows a parent peak with an odd mass for the molecular ion. What does this tell you about the amine?

A) The amine is a primary amine.

B) The amine is a secondary amine.

C) The amine contains an even number of N atoms.

D) The amine contains an odd number of N atoms.

24) What is a typical characteristic absorption in the IR spectrum of a primary amine?

A) Two N-H absorptions at 2500-2600 cm-1

B) One N-H absorption at 2500-2600 cm-1

C) Two N-H absorptions at 3300-3500 cm-1

D) One N-H absorption at 3300-3500 cm-1

25) A compound with molecular formula C6H15N exhibits a singlet at d 0.9 (1H), a triplet at d 1.10 (3H), a singlet at d1.15 (9H), and a quartet at d 2.6 (2H) in its 1HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the structure of this compound?

A) I

B) II

C) III

D) IV

26) What is the name given to naturally occurring amines derived from plant sources?

A) Enamines

B) Imines

C) Alkaloids

D) Alkamines

27) Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method for preparing primary amines?

A) NH3 is not a nucleophile.

B) Elimination will occur.

C) NH3 is too bulky to act as a nucleophile.

D) Polyalkylation of the amine will result in multiple products.

28) In the preparation of primary amines, how can direct nucleophilic substitution between NH3 and alkyl halide be made more practical than reacting NH3 and the alkyl halide in a 1:1 ratio?

A) Use a large excess of NH3.

B) Use a large excess of alkyl halide.

C) Use a limited amount of NH3.

D) Make the alkyl halide sterically hindered.

29) Why is the N-H bond of an imide especially acidic?

A) The conjugate base is stabilized by electron-donating inductive effect.

B) The conjugate base is stabilized by resonance.

C) The conjugate acid is stabilized by resonance.

D) The conjugate base is stabilized by intramolecular hydrogen bonding.

30) Which of the following alkyl halides cannot be used to prepare primary amines by the Gabriel synthesis?

A) 2-Bromo-2-methylbutane

B) 1-Bromo-2-methylbutane

C) 2-Bromo-3-methylbutane

D) 1-Bromo-3-methylbutane

31) Predict the product(s) of the following reaction.

A) I

B) II

C) III

D) None of the choices

32) What is the major organic product obtained in the following reaction?

A) I

B) II

C) III

D) IV

33) What is the major organic product obtained in the following reaction?

A) I

B) II

C) III

D) IV

34) What is the major organic product obtained in the following reaction?

A) I

B) II

C) III

D) IV

35) What is the major organic product obtained in the following reaction?

A) I

B) II

C) III

D) IV

36) Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)?

A) Because of the electron-withdrawing inductive effect of the alkyl groups

B) Because of the steric hindrance of the alkyl groups

C) Because of the resonance delocalization of the alkyl groups

D) Because of electron-donating inductive effect of the alkyl groups

37) Why are alkylamines more basic than arylamines?

A) The lone pair electrons are localized in alkylamines and delocalized in arylamines.

B) The lone pair electrons are delocalized in alkylamines and localized in arylamines.

C) The lone pair electrons are less readily available in alkylamines.

D) The lone pair electrons are more readily available in arylamines.

38) Rank the following compounds in order of increasing basicity, putting the least basic compound first.

A) III < II < IV < I

B) II < III < IV < I

C) I < IV < II < III

D) III < I < II < IV

39) Rank the following compounds in order of decreasing basicity, putting the most basic compound first.

A) II > I > III > IV

B) I > II > III > IV

C) I > III > II > IV

D) IV > II > III > I

40) Rank the following compounds in order of increasing basicity, putting the least basic first.

A) II < III < IV < I

B) I < II < III < IV

C) IV < III < II < I

D) II < I < III < IV

41) Rank the following compounds in order of decreasing basicity, putting the most basic first.

A) I > II > III > IV

B) I > III > II > IV

C) IV > III > I > II

D) II > I > III > IV

42) Why is pyrrole much less basic than pyridine?

A) The lone pair of electrons in pyrrole is located on an sp2 orbital.

B) The lone pair of electrons in pyrrole is part of the aromatic p system.

C) The lone pair of electrons in pyrrole is not part of the aromatic p system.

D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine.

43) Why is piperidine a stronger base than pyridine?

A) The lone pair of electrons in pyridine is part of the delocalized p system.

B) Aromatic compounds are always less basic than non-aromatic compounds.

C) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital.

D) The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp2 hybrid orbital.

44) Rank the following compounds in increasing order of basicity, putting the least basic first.

A) II < I < IV < III

B) I < III < II < IV

C) IV < II < III < I

D) I < II < III < IV

45) Rank the nitrogen atoms in chloroquine, shown below, in order of decreasing basicity, putting the most basic nitrogen atom first.

A) N1 > N2 > N3

B) N2 > N1 > N3

C) N3 > N2 > N1

D) N3 > N1 > N2

46) Histamine, a vasodilator, is responsible for a wide variety of physiological effects. Rank the three nitrogen atoms in histamine in increasing order of basicity, putting least basic nitrogen atom first.

A) N2 < N1 < N3

B) N1 < N2 < N3

C) N3 < N1 < N2

D) N3 < N2 < N1

47) Predict the major organic product of the following reaction.

A) I

B) II

C) III

D) IV

48) Predict the major organic product of the following reaction.

A) I

B) II

C) III

D) IV

49) Predict the major organic product of the following reaction.

A) I

B) II

C) III

D) IV

50) Predict the major organic product of the following reaction.

A) I

B) II

C) III

D) IV

51) Predict the major product of the following reaction.

A) I

B) II

C) III

D) IV

52) Predict the major product of the following reaction.

A) I

B) II

C) III

D) IV

53) Select the reagent(s) required for the following transformation.

A) NaI

B) (1) NaNO2, HCl; (2) NaI

C) (1) NaNO2, HCl; (2) I2

D) I2

54) Select the reagent(s) required for the following transformation.

A) NaF

B) (1) NaNO2, HCl; (2) F2

C) (1) NaNO2, HCl; (2) HBF4

D) F2

55) Select the reagent(s) required for the following transformation.

A) (1) NaNO2, HCl; (2) H2

B) (1) NaNO2, HCl; (2) H2O

C) (1) NaNO2, HCl; (2) H3PO4

D) (1) NaNO2, HCl; (2) H3PO2

56) Predict the major product of the following reaction.

A) I

B) II

C) III

D) IV

57) Predict the major product of the following reaction.

A) I

B) II

C) III

D) IV

58) What starting materials are required to synthesize the following azo compound?

A) I

B) II

C) III

D) IV

59) Consider the following multistep synthesis.

What is the structure of intermediate A?

A) I

B) II

C) III

D) IV

60) Consider the following multistep synthesis.

What is the structure of intermediate B?

A) I

B) II

C) III

D) IV

61) Consider the following multistep synthesis.

What is the structure of intermediate C?

A) I

B) II

C) III

D) IV

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

A) (E,R)-4-chloro-3-penten-2-amine

B) (E,S)-4-chloro-3-penten-2-amine

C) (Z,R)-4-chloro-3-penten-2-amine

D) (Z,S)-4-chloro-3-penten-2-amine

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

A) (E,R)-4-chloro-3-penten-2-amine

B) (E,S)-4-chloro-3-penten-2-amine

C) (Z,R)-4-chloro-3-penten-2-amine

D) (Z,S)-4-chloro-3-penten-2-amine

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

A) I

B) II

C) III

D) IV

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

A) I

B) II

C) III

D) IV