Question 1

Which of the following sets of reagents would accomplish the reaction shown below?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E) 
  D

Question 2

Which of the following is not limited to the synthesis of primary amines (R-NH2 or Ar-NH2)(i.e.,which,if any,can be used to make 2° or 3° amines)?

Accepted Answer

A)  Gabriel synthesis 
B)  Reduction of amides with LAH 
C)  Hofmann rearrangement 
D)  Reduction of nitriles with LAH 
E)  Reduction of nitro groups with Fe/HCl 
A)  Gabriel synthesis 
B)  Reduction of amides with LAH 
C)  Hofmann rearrangement 
D)  Reduction of nitriles with LAH 
E)  Reduction of nitro groups with Fe/HCl B

Question 3

Which of the following is not formed as either an intermediate along the reaction pathway or as a final product for the Mannich reaction shown below?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E) 
  C

Question 4

What is the structure of lithium diisopropylamide (LDA)?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 5

Rank the following in order of decreasing basicity (most basic on left):

Accepted Answer

A)  Z > X > Y 
B)  Y > X > Z 
C)  Z > Y > X 
D)  X > Z > Y 
E)  X > Y > Z 
A)  Z > X > Y 
B)  Y > X > Z 
C)  Z > Y > X 
D)  X > Z > Y 
E)  X > Y > Z

Question 6

What by-product(s)would you expect to contaminate methyl amine prepared by the following reaction?

Accepted Answer

A)  (CH3)2NH 
B)  (CH3)3N 
C)  (CH3)4N+ I- 
D)  All of the above. 
E)  None of the above. 
A)  (CH3)2NH 
B)  (CH3)3N 
C)  (CH3)4N+ I- 
D)  All of the above. 
E)  None of the above.

Question 7

What would be formed in the following reaction?

Accepted Answer

A)  CH3NH2 
B)  (CH3)2NH 
C)  (CH3)3N 
D)  None of these. 
E)  All of these. 
A)  CH3NH2 
B)  (CH3)2NH 
C)  (CH3)3N 
D)  None of these. 
E)  All of these.

Question 8

Which of the following products would you expect to result from the following reactions?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 9

Which of the molecules below is the strongest base?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 10

What process accomplishes the following transformation?

Accepted Answer

A)  Gabriel synthesis 
B)  Hofmann rearrangement 
C)  Reductive amination 
D)  Mannich reaction 
E)  Hofmann elimination 
A)  Gabriel synthesis 
B)  Hofmann rearrangement 
C)  Reductive amination 
D)  Mannich reaction 
E)  Hofmann elimination

Question 11

What product would result from the following reaction?

Accepted Answer

A) 
    
B) 
  
C) 
  
D) 
  
E) 
  
A) 
    
B) 
  
C) 
  
D) 
  
E)

Question 12

Which of the following represents N-ethyl-2-phenylethylamine?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 13

What product would result from the Hofmann elimination of the following quaternary ammonium hydroxide?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 14

Predict the major organic product of the following reaction.

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 15

Which of the following structures is a secondary amine?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 16

Absorptions at 3358 cm-1 and 3283 cm-1 in the IR spectrum would suggest which of the following compounds?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  cannot tell from the absorption data 
A) 
  
B) 
  
C) 
  
D) 
  
E)  cannot tell from the absorption data

Question 17

What is the result of the reaction shown?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 18

What major product would you expect from the reaction shown?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 19

N-nitrosoamines (called nitrosamines)have what outstanding characteristic?

Accepted Answer

A)  An intense fishy odor 
B)  Tend to be carcinogenic 
C)  Ammonia-like odor 
D)  Easily rearrange 
E)  Have acidic N-H hydrogens 
A)  An intense fishy odor 
B)  Tend to be carcinogenic 
C)  Ammonia-like odor 
D)  Easily rearrange 
E)  Have acidic N-H hydrogens

Question 20

Which of the following reactions can be used to prepare ethylamine?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above.

Exam 21: Amines and Their Derivatives: Functional Groups Containing Nitrogen

Which of the following sets of reagents would accomplish the reaction shown below?

Which of the following is not limited to the synthesis of primary amines (R-NH2 or Ar-NH2)(i.e.,which,if any,can be used to make 2° or 3° amines)?

Which of the following is not formed as either an intermediate along the reaction pathway or as a final product for the Mannich reaction shown below?

What is the structure of lithium diisopropylamide (LDA)?

Rank the following in order of decreasing basicity (most basic on left):

What by-product(s)would you expect to contaminate methyl amine prepared by the following reaction?

What would be formed in the following reaction?

Which of the following products would you expect to result from the following reactions?

Which of the molecules below is the strongest base?

What process accomplishes the following transformation?

What product would result from the following reaction?

Which of the following represents N-ethyl-2-phenylethylamine?

What product would result from the Hofmann elimination of the following quaternary ammonium hydroxide?

Predict the major organic product of the following reaction.

Which of the following structures is a secondary amine?

Absorptions at 3358 cm-1 and 3283 cm-1 in the IR spectrum would suggest which of the following compounds?

What is the result of the reaction shown?

What major product would you expect from the reaction shown?

N-nitrosoamines (called nitrosamines)have what outstanding characteristic?

Which of the following reactions can be used to prepare ethylamine?

Structure and Bonding in Organic Molecules

Structure and Reactivity: Acids and Bases,polar and Nonpolar Molecules

Reactions of Alkanes: Bond-Dissociation Energies,radical Halogenation,and Relative Reactivity

Cycloalkanes

Stereoisomers

Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution

Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Hydroxy of Functional Group: Alcohols: Properties,preparation,and Strategy of Synthesis

Further Reactions of Alcohols and the Chemistry of Ethers

Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure

Alkenes: Infrared Spectroscopy and Mass Spectrometry

Reactions to Alkenes

Alkynes: the Carbon

Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy Interlude

Benzene and Aromaticity: Electrophilic Aromatic Substitution

Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Aldehydes and Ketones: the Carbonyl Group

Enols,enolates,and the Aldol Condensation: A,b-Unsaturated Aldehydes and Ketones

Carboxylic Acids

Carboxylic Acid Derivatives

Chemistry of the Benzene Substituents: Alkylbenzenes,phenols,and Benzenamines

Ester Enolates and the Claisen Condensation: Synthesis of B-Dicarbonyl Compounds; Acyl Anion Equivalents

Carbohydrates: Polyfunctional Compounds in Nature

Heterocycles: Heteroatoms in Cyclic Organic Compounds

Amino Acids,peptides,proteins,and Nucleic Acids: Nitrogen-Containing Polymers in Nature

Filters

Which of the following is not limited to the synthesis of primary amines (R-NH₂ or Ar-NH₂)(i.e.,which,if any,can be used to make 2° or 3° amines)?

Absorptions at 3358 cm^-1 and 3283 cm^-1 in the IR spectrum would suggest which of the following compounds?