Question 1

Provide the IUPAC name for the compound shown below.

Accepted Answer

3,3-dimeth

Question 2

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 3

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

Question 4

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 
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 5

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 6

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 7

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

Accepted Answer

Question 8

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

Accepted Answer

p-nitroaniline < ani

Question 9

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

Accepted Answer

triethylamine < di-n

Question 10

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 11

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

Accepted Answer

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

Question 12

Which of the following amines is most basic?

Accepted Answer

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

Question 13

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

Question 14

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 15

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 16

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

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

Question 17

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

Question 18

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

Question 19

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 20

Provide the formula for nitrous acid.

Accepted Answer

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

Exam 19: Amines

Provide the IUPAC name for the compound shown below.

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

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

Identify the correct name for the following structure.

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

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

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

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

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

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

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

Which of the following amines is most basic?

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

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

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

Complete the following reaction by filling in the necessary reagents.

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

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

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

Provide the formula for nitrous acid.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

If ethanol has a pK_a value of 16, what is the pK_b value of the ethoxide anion?

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