Question 1

What is the IUPAC name of the following compound?

Accepted Answer

A)  1-methyl-N-propyl-1-propanamine
B)  4-methyl-4-heptanamine
C)  2-propyl-3-hexanamine
D)  N-propyl-2-pentanamineE) A) and B)
F) A) and D)

Question 2

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) A) and C)

Question 3

What is the common name of the following compound?

Accepted Answer

A)  diisopropylamine
B)  dipropylamine
C)  diisopropanamine
D)  dibutylamineE) None of the above
F) All of the above

Question 4

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?

Accepted Answer

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 temperatureE) B) and D)
F) B) and C)

Question 5

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.

Accepted Answer

A)  N2 
B)  N1 
C)  N3 
D)  N3 < N2 < N1E) B) and D)
F) All of the above

Question 6

Rank the nitrogen atoms in chloroquine,shown below,in order of decreasing basicity,putting the most basic nitrogen atom first.  N2 > N3 B) N2 > N1 > N3 C) N3 > N2 > N1 D) N3 > N1 > N2" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  N1 > N2 > N3
B)  N2 > N1 > N3
C)  N3 > N2 > N1
D)  N3 > N1 > N2E) None of the above
F) A) and B)

Question 7

What is the common name of the following compound?

Accepted Answer

A)  isopropylamine
B)  2-methyl-2-propanamine
C)  tert-butylamine
D)  isobutylamineE) A) and D)
F) B) and C)

Question 8

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

Accepted Answer

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-1E) A) and D)
F) A) and B)

Question 9

Consider the following multistep synthesis.  What is the structure of intermediate B?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) A) and C)

Question 10

Predict the product(s) of the following reaction.

Accepted Answer

A)  I
B)  II
C)  III
D)  None of the choicesE) A) and D)
F) C) and D)

Question 11

Rank the following compounds in order of decreasing basicity,putting the most basic compound first.  I > III > IV B) I > II > III > IV C) I > III > II > IV D) IV > II > III > I" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  II > I > III > IV
B)  I > II > III > IV
C)  I > III > II > IV
D)  IV > II > III > IE) A) and B)
F) A) and C)

Question 12

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?

Accepted Answer

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.E) None of the above
F) B) and C)

Question 13

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

Accepted Answer

A)  2-Bromo-2-methylbutane
B)  1-Bromo-2-methylbutane
C)  2-Bromo-3-methylbutane
D)  1-Bromo-3-methylbutaneE) A) and C)
F) C) and D)

Question 14

What is the common name of the following compound?

Accepted Answer

A)  Isopropylamine
B)  Sec-butylamine
C)  2-Methyl-1-propanamine
D)  IsobutylamineE) B) and D)
F) B) and C)

Question 15

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?

Accepted Answer

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.E) C) and D)
F) B) and C)

Question 16

Arrange the following compounds in order of decreasing boiling point,putting the compound with the highest boiling point first.  II > III B) I > III > II C) III > I > II D) III > II > I" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  I > II > III
B)  I > III > II
C)  III > I > II
D)  III > II > IE) A) and D)
F) C) and D)

Question 17

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

Accepted Answer

A)  I
B)  II
C)  III
D)  I and IIE) C) and D)
F) A) and B)

Question 18

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

Accepted Answer

A)  I
B)  II
C)  III
D)  I and IIE) B) and C)
F) C) and D)

Question 19

What is the IUPAC name of the following compound?

Accepted Answer

A)  N-ethyl-N-methylpentylamine
B)  N-ethyl-N-methyl-1-pentanamine
C)  N-methyl-3-octanamine
D)  N-ethyl-2-heptanamineE) None of the above
F) C) and D)

Question 20

Predict the major product of the following reaction.

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) A) and C)

Exam 23: Amines

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?

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What is the common name of the following compound?

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What is the IUPAC name of the following compound?

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

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

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What is the IUPAC name of the following compound?

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Consider the following multistep synthesis. What is the structure of intermediate B?

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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?

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What is the common name of the following compound?

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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?

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Predict the major product of the following reaction.

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

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What is the common name of the following compound?

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

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

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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.

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

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

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

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Predict the product(s) of the following reaction.

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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?

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