Question 1

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-heptanamine 
A) N-ethyl-N-methylpentylamine 
B) N-ethyl-N-methyl-1-pentanamine 
C) N-methyl-3-octanamine 
D) N-ethyl-2-heptanamine

Question 2

Predict the product(s)of the following reaction.

Accepted Answer

A) I 
B) II 
C) III 
D) None of the choices 
A) I 
B) II 
C) III 
D) None of the choices

Question 3

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 4

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

Accepted Answer

A) I > II > III 
B) I > III > II 
C) III > I > II 
D) III > II > I 
A) I > II > III 
B) I > III > II 
C) III > I > II 
D) III > II > I

Question 5

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

Accepted Answer

A) II > I > III > IV 
B) I > II > III > IV 
C) I > III > II > IV 
D) IV > II > III > I 
A) II > I > III > IV 
B) I > II > III > IV 
C) I > III > II > IV 
D) IV > II > III > I

Question 6

Predict the major product of the following reaction.

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 7

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-1 
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

Question 8

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

Accepted Answer

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

Question 9

What is the common name of the following compound?

Accepted Answer

A) Isopropylamine 
B) Sec-butylamine 
C) 2-Methyl-1-propanamine 
D) Isobutylamine 
A) Isopropylamine 
B) Sec-butylamine 
C) 2-Methyl-1-propanamine 
D) Isobutylamine

Question 10

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

Question 11

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 12

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

Accepted Answer

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

Question 13

What is the common name of the following compound?

Accepted Answer

A) isopropylamine 
B) 2-methyl-2-propanamine 
C) tert-butylamine 
D) isobutylamine 
A) isopropylamine 
B) 2-methyl-2-propanamine 
C) tert-butylamine 
D) isobutylamine

Question 14

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

Accepted Answer

A) N1 > N2 > N3 
B) N2 > N1 > N3 
C) N3 > N2 > N1 
D) N3 > N1 > N2 
A) N1 > N2 > N3 
B) N2 > N1 > N3 
C) N3 > N2 > N1 
D) N3 > N1 > N2

Question 15

What is the common name of the following compound?

Accepted Answer

A) diisopropylamine 
B) dipropylamine 
C) diisopropanamine 
D) dibutylamine 
A) diisopropylamine 
B) dipropylamine 
C) diisopropanamine 
D) dibutylamine

Question 16

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 temperature 
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

Question 17

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. 
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.

Question 18

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 < N1 < N3 
B) N1 < N2 < N3 
C) N3 < N1 < N2 
D) N3 < N2 < N1 
A) N2 < N1 < N3 
B) N1 < N2 < N3 
C) N3 < N1 < N2 
D) N3 < N2 < N1

Question 19

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-methylbutane 
A) 2-Bromo-2-methylbutane 
B) 1-Bromo-2-methylbutane 
C) 2-Bromo-3-methylbutane 
D) 1-Bromo-3-methylbutane

Question 20

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. 
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.

Exam 23: Amines

What is the IUPAC name of the following compound?

Predict the product(s)of the following reaction.

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

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

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

Predict the major product of the following reaction.

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

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

What is the common name of the following compound?

What is the IUPAC name of the following compound?

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

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

What is the common name of the following compound?

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

What is the common name of the following compound?

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?

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?

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.

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

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?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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?