Question 1

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 2

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 3

Why are alkylamines more basic than arylamines?

Accepted Answer

A) The lone pair electrons are localized in alkylamines and delocalized in arylamines. 
B) The lone pair electrons are delocalized in alkylamines and localized in arylamines. 
C) The lone pair electrons are less readily available in alkylamines. 
D) The lone pair electrons are more readily available in arylamines. 
A) The lone pair electrons are localized in alkylamines and delocalized in arylamines. 
B) The lone pair electrons are delocalized in alkylamines and localized in arylamines. 
C) The lone pair electrons are less readily available in alkylamines. 
D) The lone pair electrons are more readily available in arylamines.

Question 4

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

Accepted Answer

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

Question 5

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

Accepted Answer

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

Question 6

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 7

Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?

Accepted Answer

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) 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.

Question 8

What is the IUPAC name of the following compound?

Accepted Answer

A) (S)-methyl-4-hexanamine 
B) (S)-5-methyl-3-hexanamine 
C) (R)-2-methyl-4-hexanamine 
D) (R)-5-methyl-3-hexanamine 
A) (S)-methyl-4-hexanamine 
B) (S)-5-methyl-3-hexanamine 
C) (R)-2-methyl-4-hexanamine 
D) (R)-5-methyl-3-hexanamine

Question 9

What is the IUPAC name of the following compound?

Accepted Answer

A) N-ethyl-N-methylcyclopentanamine 
B) N-cyclopentyl-N-methylethanamine 
C) N-methyl-N-ethylcyclopentylamine 
D) N-ethyl-N-methylpentanamine 
A) N-ethyl-N-methylcyclopentanamine 
B) N-cyclopentyl-N-methylethanamine 
C) N-methyl-N-ethylcyclopentylamine 
D) N-ethyl-N-methylpentanamine

Question 10

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 11

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 12

Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method for preparing primary amines?

Accepted Answer

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. 
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.

Question 13

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 14

What is the major organic product obtained in the following reaction?

Accepted Answer

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

Question 15

Select the reagent(s) required for the following transformation.

Accepted Answer

A) NaF 
B) (1) NaNO2, HCl; (2) F2 
C) (1) NaNO2, HCl; (2) HBF4 
D) F2 
A) NaF 
B) (1) NaNO2, HCl; (2) F2 
C) (1) NaNO2, HCl; (2) HBF4 
D) F2

Question 16

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 17

Select the reagent(s) required for the following transformation.

Accepted Answer

A) (1) NaNO2, HCl; (2) H2 
B) (1) NaNO2, HCl; (2) H2O 
C) (1) NaNO2, HCl; (2) H3PO4 
D) (1) NaNO2, HCl; (2) H3PO2 
A) (1) NaNO2, HCl; (2) H2 
B) (1) NaNO2, HCl; (2) H2O 
C) (1) NaNO2, HCl; (2) H3PO4 
D) (1) NaNO2, HCl; (2) H3PO2

Question 18

Select the reagent(s) required for the following transformation.

Accepted Answer

A) NaI 
B) (1) NaNO2, HCl; (2) NaI 
C) (1) NaNO2, HCl; (2) I2 
D) I2 
A) NaI 
B) (1) NaNO2, HCl; (2) NaI 
C) (1) NaNO2, HCl; (2) I2 
D) I2

Question 19

Predict the major organic product of the following reaction.

Accepted Answer

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

Question 20

What is the major organic product obtained in the following reaction?

Accepted Answer

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

Exam 25: Amines

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

Predict the major product of the following reaction.

Why are alkylamines more basic than arylamines?

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

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

What is the common name of the following compound?

Why should the chirality of an ammonium salt with four different groups on the nitrogen atom not be ignored?

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

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

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.

Why is direct nucleophilic substitution of an alkyl halide with NH3 not a very useful method for preparing primary amines?

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?

What is the major organic product obtained in the following reaction?

Select the reagent(s) required for the following transformation.

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

Select the reagent(s) required for the following transformation.

Select the reagent(s) required for the following transformation.

Predict the major organic product of the following reaction.

What is the major organic product obtained in the following reaction?

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

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Filters

Why is direct nucleophilic substitution of an alkyl halide with NH₃ not a very useful method for preparing primary amines?