Question 1

Why is pyrrole much less basic than pyridine?

Accepted Answer

A) The lone pair of electrons in pyrrole is located on an sp2 orbital. 
B) The lone pair of electrons in pyrrole is part of the aromatic p system. 
C) The lone pair of electrons in pyrrole is not part of the aromatic p system. 
D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine. 
A) The lone pair of electrons in pyrrole is located on an sp2 orbital. 
B) The lone pair of electrons in pyrrole is part of the aromatic p system. 
C) The lone pair of electrons in pyrrole is not part of the aromatic p system. 
D) The pKa of the conjugate acid of pyrrole is much greater than the conjugate acid of pyridine. B

Question 2

What is the IUPAC name of the following compound?

Accepted Answer

A) N-propylhexanamine 
B) N-propylaniline 
C) N-ethylcyclohexylamine 
D) N-propylcyclohexanamine 
A) N-propylhexanamine 
B) N-propylaniline 
C) N-ethylcyclohexylamine 
D) N-propylcyclohexanamine D

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 B

Question 4

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 5

What is the correct assignment of the names of the following aromatic amines?

Accepted Answer

A) I = pyrrolidine; II = pyrimidine; III = aniline. 
B) I = pyrrole; II = pyrimidine; III = anisole. 
C) I = pyrrolidine; II = pyridine; III =aniline. 
D) I = pyrrole; II = pyridine; III = aniline. 
A) I = pyrrolidine; II = pyrimidine; III = aniline. 
B) I = pyrrole; II = pyrimidine; III = anisole. 
C) I = pyrrolidine; II = pyridine; III =aniline. 
D) I = pyrrole; II = pyridine; III = aniline.

Question 6

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 7

What is the approximate bond angle of the substituents around a nitrogen atom in amines?

Accepted Answer

A) 90° 
B) 109.5° 
C) 120° 
D) 180° 
A) 90° 
B) 109.5° 
C) 120° 
D) 180°

Question 8

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 9

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 10

Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)?

Accepted Answer

A) Because of the electron-withdrawing inductive effect of the alkyl groups 
B) Because of the steric hindrance of the alkyl groups 
C) Because of the resonance delocalization of the alkyl groups 
D) Because of electron-donating inductive effect of the alkyl groups 
A) Because of the electron-withdrawing inductive effect of the alkyl groups 
B) Because of the steric hindrance of the alkyl groups 
C) Because of the resonance delocalization of the alkyl groups 
D) Because of electron-donating inductive effect of the alkyl groups

Question 11

Why is the N-H bond of an imide especially acidic?

Accepted Answer

A) The conjugate base is stabilized by electron-donating inductive effect. 
B) The conjugate base is stabilized by resonance. 
C) The conjugate acid is stabilized by resonance. 
D) The conjugate base is stabilized by intramolecular hydrogen bonding. 
A) The conjugate base is stabilized by electron-donating inductive effect. 
B) The conjugate base is stabilized by resonance. 
C) The conjugate acid is stabilized by resonance. 
D) The conjugate base is stabilized by intramolecular hydrogen bonding.

Question 12

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

Question 14

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 15

Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first.

Accepted Answer

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

Question 16

What is the IUPAC name of the following compound?

Accepted Answer

A) 3-methyl-1-hexanamine 
B) 4-methyl-1-hexylamine 
C) 4-methyl-1-hexanamine 
D) 3-methyl-6-hexylamine 
A) 3-methyl-1-hexanamine 
B) 4-methyl-1-hexylamine 
C) 4-methyl-1-hexanamine 
D) 3-methyl-6-hexylamine

Question 17

What is the common name of the following compound?

Accepted Answer

A) isopropylamine 
B) sec-butylamine 
C) isobutylamine 
D) tert-butylamine 
A) isopropylamine 
B) sec-butylamine 
C) isobutylamine 
D) tert-butylamine

Question 18

Rank the following compounds in order of increasing basicity, putting the least basic first.

Accepted Answer

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

Question 19

What is the name given to naturally occurring amines derived from plant sources?

Accepted Answer

A) Enamines 
B) Imines 
C) Alkaloids 
D) Alkamines 
A) Enamines 
B) Imines 
C) Alkaloids 
D) Alkamines

Question 20

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

Exam 25: Amines

Why is pyrrole much less basic than pyridine?

What is the IUPAC name of the following compound?

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

Predict the major organic product of the following reaction.

What is the correct assignment of the names of the following aromatic amines?

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

What is the approximate bond angle of the substituents around a nitrogen atom in amines?

Predict the major organic product of the following reaction.

Predict the major product of the following reaction.

Why are 1°, 2°, and 3° alkylamines more basic than ammonia (NH3)?

Why is the N-H bond of an imide especially acidic?

Predict the major product of the following reaction.

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

Predict the major organic product of the following reaction.

Arrange the following amines in order of decreasing water solubility, putting the most soluble amine first.

What is the IUPAC name of the following compound?

What is the common name of the following compound?

Rank the following compounds in order of increasing basicity, putting the least basic first.

What is the name given to naturally occurring amines derived from plant sources?

Predict the product(s) of 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 are 1°, 2°, and 3° alkylamines more basic than ammonia (NH₃)?