Question 1

Identify the correct name for the following structure.

Accepted Answer

A)   5-methyl-4-methylaminocyclohept-5-enol
B)   5-hydroxy-2,N-dimethylcyclohept-2-enamine
C)   4-hydroxy-7,N-dimethylcyclohept-6-enamine
D)   4-methyl-5-methylaminocyclohept-3-enol

Question 2

Rank the following compounds in order of increasing boiling point (lowest to highest): triethylamine, cyclohexylamine, di-n-propylamine.

Accepted Answer

triethylamine < di-n...

Question 3

Arrange the following in order of increasing basicity:
aniline, p-nitroaniline, p-toluidine, and p-methoxyaniline.

Accepted Answer

p-nitroaniline < ani...

Question 4

Devise an efficient method for preparing m-cresol from m-toluidine.

Accepted Answer

The answer of Devise an efficient method for preparing m-cresol...

Question 5

Provide the IUPAC name for the compound shown below.

Accepted Answer

3,3-dimeth...

Question 6

Heating a(n)  ________ results in a Cope elimination.

Accepted Answer

A)   amine oxide
B)   imine
C)   enamine
D)   oxime
E)   quaternary ammonium salt

Question 7

Provide the structure of the major organic product in the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 8

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with n-propylamine.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 9

Which of the following amines is most basic?

Accepted Answer

A)   aniline
B)   N-ethylaniline
C)   N,N-diethylaniline
D)   piperidine
E)   pyrrole

Question 10

The α-carbon atom bonded to the nitrogen of an alkylamine usually appears in what chemical shift (δ)  range?

Accepted Answer

A)   5-20
B)   30-50
C)   80-100
D)   120-150
E)   180-220

Question 11

A sample of cyclohexylamine is contaminated with considerable hydrocarbon impurity. How might the sample be purified using a technique based on solubility differences?

Accepted Answer

Dissolve sample in ether. Wash with dilu...

Question 12

Which of the following would be the best phase transfer catalyst?

Accepted Answer

A)   N(CH3) 4I
B)   N((CH2) 5CH3) 4I
C)   NH4Br
D)   N((CH2) 3CH3) 3

Question 13

Provide the formula for nitrous acid.

Accepted Answer

The answer of Provide the formula for nitrous acid....

Question 14

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 15

How might one distinguish a sample of n-butylamine from a sample of diethylamine using IR spectroscopy?

Accepted Answer

Primary amines, like n-butylam...

Question 16

Provide the structure of the major organic product in the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 17

Pyridine typically undergoes electrophilic aromatic substitution ________ rapidly than benzene, and its preferred site of substitution is the ________ - position.

Accepted Answer

A)   more, 2
B)   more, 3
C)   more, 4
D)   less, 2
E)   less, 3

Question 18

If ethanol has a pKa value of 16, what is the pKb value of the ethoxide anion?

Accepted Answer

Question 19

How might the presence of an N-H functionally be indicated using NMR spectroscopy?

Accepted Answer

Like the O-H group, the N-H group underg...

Question 20

Why can 1,2,2-trimethylaziridine be resolved into enantiomers while N-methyl-1-propanamine cannot?

Accepted Answer

In 1,2,2-trimethylaziridine the nitrogen...

Exam 19: Amines

How might the presence of an N-H functionally be indicated using NMR spectroscopy?

Correct AnswerverifiedLike the O-H group, the N-H group underg...View AnswerShow Answer

If ethanol has a pKa value of 16, what is the pKb value of the ethoxide anion?

Correct AnswerverifiedShow Answer

Identify the correct name for the following structure.

Correct AnswerverifiedShow Answer

How might one distinguish a sample of n-butylamine from a sample of diethylamine using IR spectroscopy?

Correct AnswerverifiedPrimary amines, like n-butylam...View AnswerShow Answer

Arrange the following in order of increasing basicity: aniline, p-nitroaniline, p-toluidine, and p-methoxyaniline.

Correct Answerverifiedp-nitroaniline < ani...View AnswerShow Answer

Pyridine typically undergoes electrophilic aromatic substitution ________ rapidly than benzene, and its preferred site of substitution is the ________ - position.

Correct AnswerverifiedShow Answer

Devise an efficient method for preparing m-cresol from m-toluidine.

Correct AnswerverifiedShow Answer

The α-carbon atom bonded to the nitrogen of an alkylamine usually appears in what chemical shift (δ) range?

Correct AnswerverifiedShow Answer

Provide the structure of the major organic product in the reaction below.

Correct AnswerverifiedShow Answer

Heating a(n) ________ results in a Cope elimination.

Correct AnswerverifiedShow Answer

Provide the IUPAC name for the compound shown below.

Correct Answerverified3,3-dimeth...View AnswerShow Answer

Why can 1,2,2-trimethylaziridine be resolved into enantiomers while N-methyl-1-propanamine cannot?

Correct AnswerverifiedIn 1,2,2-trimethylaziridine the nitrogen...View AnswerShow Answer

Which of the following would be the best phase transfer catalyst?

Correct AnswerverifiedShow Answer

Provide the formula for nitrous acid.

Correct AnswerverifiedShow Answer

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with n-propylamine.

Correct AnswerverifiedShow Answer

Provide the structure of the major organic product in the reaction below.

Correct AnswerverifiedShow Answer

Rank the following compounds in order of increasing boiling point (lowest to highest): triethylamine, cyclohexylamine, di-n-propylamine.

Correct Answerverifiedtriethylamine < di-n...View AnswerShow Answer

A sample of cyclohexylamine is contaminated with considerable hydrocarbon impurity. How might the sample be purified using a technique based on solubility differences?

Correct AnswerverifiedDissolve sample in ether. Wash with dilu...View AnswerShow Answer

Complete the following reaction by filling in the necessary reagents.

Correct AnswerverifiedShow Answer

Which of the following amines is most basic?

Correct AnswerverifiedShow Answer

Correct Answer
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Like the O-H group, the N-H group underg...
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If ethanol has a pK_a value of 16, what is the pK_b value of the ethoxide anion?

Correct Answer
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Correct Answer
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Primary amines, like n-butylam...
View Answer

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p-nitroaniline < ani...
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Pyridine typically undergoes electrophilic aromatic substitution rapidly than benzene, and its preferred site of substitution is the - position.

Correct Answer
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Correct Answer
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Correct Answer
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3,3-dimeth...
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In 1,2,2-trimethylaziridine the nitrogen...
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triethylamine < di-n...
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Dissolve sample in ether. Wash with dilu...
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Correct Answer
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Correct Answer
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