Question 1

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 2

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 3

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 4

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 5

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 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 the IUPAC name of the following compound?

Accepted Answer

A) (Z)-4-hexen-1-amine 
B) (
E) -4-hexen-1-amine 
C) (
E) -2-hexen-6-amine 
D) (Z)-2-hexen-6-amine 
A) (Z)-4-hexen-1-amine 
B) (
E) -4-hexen-1-amine 
C) (
E) -2-hexen-6-amine 
D) (Z)-2-hexen-6-amine

Question 8

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

Accepted Answer

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

Question 9

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 10

What is the IUPAC name for the following compound?

Accepted Answer

A) (E,R)-4-chloro-3-penten-2-amine 
B) (E,S)-4-chloro-3-penten-2-amine 
C) (Z,R)-4-chloro-3-penten-2-amine 
D) (Z,S)-4-chloro-3-penten-2-amine 
A) (E,R)-4-chloro-3-penten-2-amine 
B) (E,S)-4-chloro-3-penten-2-amine 
C) (Z,R)-4-chloro-3-penten-2-amine 
D) (Z,S)-4-chloro-3-penten-2-amine

Question 11

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 12

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 13

Why is piperidine a stronger base than pyridine?

Accepted Answer

A) The lone pair of electrons in pyridine is part of the delocalized p 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 p 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 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

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

Accepted Answer

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

Question 16

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 17

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 18

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 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 IUPAC name for the following compound?

Accepted Answer

A) (E,R)-4-chloro-3-penten-2-amine 
B) (E,S)-4-chloro-3-penten-2-amine 
C) (Z,R)-4-chloro-3-penten-2-amine 
D) (Z,S)-4-chloro-3-penten-2-amine 
A) (E,R)-4-chloro-3-penten-2-amine 
B) (E,S)-4-chloro-3-penten-2-amine 
C) (Z,R)-4-chloro-3-penten-2-amine 
D) (Z,S)-4-chloro-3-penten-2-amine

Exam 23: Amines

What is the common name of the following compound?

Why are alkylamines more basic than arylamines?

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

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

What is the IUPAC name of the following compound?

Predict the major product of the following reaction.

What is the IUPAC name of the following compound?

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

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

What is the IUPAC name for the following compound?

What is the IUPAC name of the following compound?

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

Why is piperidine a stronger base than pyridine?

Predict the major organic product of the following reaction.

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

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?

Predict the major organic product of the following reaction.

What is the IUPAC name for the following compound?

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

Why is direct nucleophilic substitution of an alkyl halide with NH₃not a very useful method for preparing primary amines?