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Smith6e Chapter23 TB
Smith6e Chapter23 TB
Chapter 23 Amines
A) I
B) II
C) III
D) I and II
A) I
B) II
C) III
D) I and II
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°
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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
A) Isopropylamine
B) Sec-butylamine
C) 2-Methyl-1-propanamine
D) Isobutylamine
A) isopropylamine
B) sec-butylamine
C) isobutylamine
D) tert-butylamine
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9) What is the common name of the following compound?
A) isopropylamine
B) 2-methyl-2-propanamine
C) tert-butylamine
D) isobutylamine
A) diisopropylamine
B) dipropylamine
C) diisopropanamine
D) dibutylamine
A) dimethylisobutylamine
B) butyldimethylamine
C) N,N-dimethylbutanamine
D) sec-butyldimethylamine
A) N-propylhexanamine
B) N-propylaniline
C) N-ethylcyclohexylamine
D) N-propylcyclohexanamine
3
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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
A) 3-methyl-1-hexanamine
B) 4-methyl-1-hexylamine
C) 4-methyl-1-hexanamine
D) 3-methyl-6-hexylamine
A) N-ethyl-N-methylcyclopentanamine
B) N-cyclopentyl-N-methylethanamine
C) N-methyl-N-ethylcyclopentylamine
D) N-ethyl-N-methylpentanamine
A) 1-methyl-N-propyl-1-propanamine
B) 4-methyl-4-heptanamine
C) 2-propyl-3-hexanamine
D) N-propyl-2-pentanamine
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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
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?
20) Arrange the following compounds in order of decreasing boiling point, putting the compound
with the highest boiling point first.
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D) III > II > I
21) Arrange the following compounds in order of increasing boiling point, putting the compound
with the least boiling point first.
22) Arrange the following amines in order of decreasing water solubility, putting the most
soluble amine first.
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.
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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 NH 3
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.
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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
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
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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
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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
38) Rank the following compounds in order of increasing basicity, putting the least basic
compound first.
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39) Rank the following compounds in order of decreasing basicity, putting the most basic
compound first.
40) Rank the following compounds in order of increasing basicity, putting the least basic first.
41) Rank the following compounds in order of decreasing basicity, putting the most basic first.
11
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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.
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
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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
A) I
B) II
C) III
D) IV
13
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48) Predict the major organic product of the following reaction.
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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50) Predict the major organic product of the following reaction.
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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52) Predict the major product of the following reaction.
A) I
B) II
C) III
D) IV
A) NaI
B) (1) NaNO2, HCl; (2) NaI
C) (1) NaNO2, HCl; (2) I2
D) I2
A) NaF
B) (1) NaNO2, HCl; (2) F2
C) (1) NaNO2, HCl; (2) HBF4
D) F2
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55) Select the reagent(s) required for the following transformation.
A) I
B) II
C) III
D) IV
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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
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59) Consider the following multistep synthesis.
A) I
B) II
C) III
D) IV
A) I
B) II
C) III
D) IV
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61) Consider the following multistep synthesis.
A) I
B) II
C) III
D) IV
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
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
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64) What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
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65) What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
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