Question 1

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 2

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 3

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 4

Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first. $$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OCH } _ { 2 } \mathrm { CH } _ { 3 } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH }$$
$$\mathrm { I }\quad\quad\quad\quad\quad\quad\mathrm { II }\quad\quad\quad\quad\quad\quad\mathrm { III }$$

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

A compound with molecular formula C6H15N exhibits a singlet at F1F1F1S1F1F1F10 0.9 (1H), a triplet at F1F1F1S1F1F1F10 1.10 (3H), a singlet at F1F1F1S1F1F1F10 1.15 (9H), and a quartet at F1F1F1S1F1F1F10 2.6 (2H) in its 1HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the structure of this compound?

Accepted Answer

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

Question 6

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 7

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 8

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

Question 9

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 10

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 11

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

Accepted Answer

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

Question 12

Why is piperidine a stronger base than pyridine?

Accepted Answer

A)  The lone pair of electrons in pyridine is part of the delocalized F1F1F1S1F1F1F10 system. 
B)  Aromatic compounds are always less basic than non-aromatic compounds. 
C)  The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital. 
D)  The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp2 hybrid orbital. 
A)  The lone pair of electrons in pyridine is part of the delocalized F1F1F1S1F1F1F10 system. 
B)  Aromatic compounds are always less basic than non-aromatic compounds. 
C)  The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp hybrid orbital. 
D)  The lone pair of electrons in piperidine is in an sp3 hybrid orbital; the lone pair of electrons in pyridine is in an sp2 hybrid orbital.

Question 13

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 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

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 16

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 17

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 18

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°

Exam 25: Amines

Predict the major product of the following reaction.

What is the IUPAC name of the following compound?

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

A compound with molecular formula C6H15N exhibits a singlet at  0.9 (1H), a triplet at  1.10 (3H), a singlet at  1.15 (9H), and a quartet at  2.6 (2H) in its 1HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm-1. What is the structure of this compound?

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

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

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

Why are alkylamines more basic than arylamines?

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

Why is piperidine a stronger base than pyridine?

Predict the product(s) of the following reaction.

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

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

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

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

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

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 Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Lipids

Synthetic Polymers

Filters

A compound with molecular formula C₆H₁₅N exhibits a singlet at  0.9 (1H), a triplet at  1.10 (3H), a singlet at  1.15 (9H), and a quartet at  2.6 (2H) in its ¹HNMR spectrum. Its IR spectrum shows one medium absorption band near 3400 cm^-1. What is the structure of this compound?

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

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