Question 1

Provide the structure of the major mononitration product(s) of the compound below.

Accepted Answer

The answer of Provide the structure of the major mononitration...

Question 2

Name the major organic product which results when 3-ethylbenzenesulfonic acid is heated in aqueous acid.

Accepted Answer

The answer of Name the major organic product which results...

Question 3

Based upon the following energy profile diagram for the first step of an electrophilic aromatic substitution reaction, which of the following substituents is X mostly likely to be?

Accepted Answer

A)  Cl 
B)  OCH3 
C)  CO2H 
D)  CH3 
A)  Cl 
B)  OCH3 
C)  CO2H 
D)  CH3

Question 4

Provide a detailed, stepwise mechanism for the following reactions.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 5

In the addition of an electrophile to acetophenone, which of the following best describes the expected mode of reaction?

Accepted Answer

A)  The o,p-positions are most activated to attack by the electrophile. 
B)  The m-positions are most activated to attack by the electrophile. 
C)  The o,p-positions are most deactivated to attack by the electrophile. 
D)  The m-positions are most deactivated to attack by the electrophile. 
E)  All positions (o, m, and p) are equally activated to attack by the electrophile. 
A)  The o,p-positions are most activated to attack by the electrophile. 
B)  The m-positions are most activated to attack by the electrophile. 
C)  The o,p-positions are most deactivated to attack by the electrophile. 
D)  The m-positions are most deactivated to attack by the electrophile. 
E)  All positions (o, m, and p) are equally activated to attack by the electrophile.

Question 6

p-Methoxybenzaldehyde can be prepared from anisole using the Gatterman-Koch formylation. What mixture of reagents is necessary for this process?

Accepted Answer

A)  CO, HCl, AlCl3, CuCl 
B)  CO, SO3, H2SO4 
C)  CO2, HCl, AlCl3 
D)  CO2, SO3, H2SO4 
E)  CO2, HNO3, H2SO4 
A)  CO, HCl, AlCl3, CuCl 
B)  CO, SO3, H2SO4 
C)  CO2, HCl, AlCl3 
D)  CO2, SO3, H2SO4 
E)  CO2, HNO3, H2SO4

Question 7

Provide a detailed, stepwise mechanism for the reaction of benzene with Br2 and FeBr3. Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism.

Accepted Answer

Question 8

Provide the major organic product(s) when benzene is treated with the following sequence of reagents: 1. Br2, FeBr3 2. HNO3, H2SO4.

Accepted Answer

Question 9

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 10

Which sequence correctly ranks the following aromatic rings in order of increasing rate of reactivity with chlorine and aluminum chloride?

Accepted Answer

A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 2 < 1 
D)  2 < 1 < 3 
E)  1 < 3 < 2 
A)  1 < 2 < 3 
B)  2 < 3 < 1 
C)  3 < 2 < 1 
D)  2 < 1 < 3 
E)  1 < 3 < 2

Question 11

Which of the following is an intermediate in the bromination of toluene?

Accepted Answer

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

Question 12

Which of the following reactions will actually yield the indicated product?

Accepted Answer

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

Question 13

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 14

Rank the following compounds in order of increasing reactivity towards chlorination with Cl2/AlCl3 (slowest reacting to fastest).

Accepted Answer

A)  3 < 4 < 2 < 1 < 5 
B)  2 < 4 < 1 < 3 < 5 
C)  4 < 2 < 1 < 3 < 5 
D)  2 < 4 < 5 < 1 < 3 
E)  2 < 4 < 1 < 5 < 3 
A)  3 < 4 < 2 < 1 < 5 
B)  2 < 4 < 1 < 3 < 5 
C)  4 < 2 < 1 < 3 < 5 
D)  2 < 4 < 5 < 1 < 3 
E)  2 < 4 < 1 < 5 < 3

Question 15

Show how the following product can be made from benzene.

Accepted Answer

1) isobutyryl chlori

Question 16

Which of the following is the best choice of reagents to effect the electrophilic iodination of an aromatic ring?

Accepted Answer

A)  KI, acetone 
B)  I2, CH3CN 
C)  KI, HNO3 
D)  I2, HNO3 
E)  none of the above 
A)  KI, acetone 
B)  I2, CH3CN 
C)  KI, HNO3 
D)  I2, HNO3 
E)  none of the above

Question 17

Which of the following compounds will undergo bromination most rapidly using Br2, FeBr3?

Accepted Answer

A)  p-methylacetanilide 
B)  bromobenzene 
C)  acetanilide 
D)  benzenesulfonic acid 
E)  dibromobenzene 
A)  p-methylacetanilide 
B)  bromobenzene 
C)  acetanilide 
D)  benzenesulfonic acid 
E)  dibromobenzene

Question 18

Why are Friedel-Crafts acylation reactions not prone to polyacylation?

Accepted Answer

Once the ring is acylated, it

Question 19

Show what reagents are needed to complete the transformation below.

Accepted Answer

The answer of Show what reagents are needed to complete...

Question 20

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Exam 17: Reactions of Aromatic Compounds

Provide the structure of the major mononitration product(s) of the compound below.

Name the major organic product which results when 3-ethylbenzenesulfonic acid is heated in aqueous acid.

Based upon the following energy profile diagram for the first step of an electrophilic aromatic substitution reaction, which of the following substituents is X mostly likely to be?

Provide a detailed, stepwise mechanism for the following reactions.

In the addition of an electrophile to acetophenone, which of the following best describes the expected mode of reaction?

p-Methoxybenzaldehyde can be prepared from anisole using the Gatterman-Koch formylation. What mixture of reagents is necessary for this process?

Provide a detailed, stepwise mechanism for the reaction of benzene with Br2 and FeBr3. Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism.

Provide the major organic product(s) when benzene is treated with the following sequence of reagents: 1. Br2, FeBr3 2. HNO3, H2SO4.

Provide the major organic product of the following reaction.

Which sequence correctly ranks the following aromatic rings in order of increasing rate of reactivity with chlorine and aluminum chloride?

Which of the following is an intermediate in the bromination of toluene?

Which of the following reactions will actually yield the indicated product?

Provide the major organic product of the following reaction.

Rank the following compounds in order of increasing reactivity towards chlorination with Cl2/AlCl3 (slowest reacting to fastest).

Show how the following product can be made from benzene.

Which of the following is the best choice of reagents to effect the electrophilic iodination of an aromatic ring?

Which of the following compounds will undergo bromination most rapidly using Br2, FeBr3?

Why are Friedel-Crafts acylation reactions not prone to polyacylation?

Show what reagents are needed to complete the transformation below.

Provide the major organic product of the following reaction.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide a detailed, stepwise mechanism for the reaction of benzene with Br₂ and FeBr₃. Make sure to include the activating reaction between Br₂ and FeBr₃ in your mechanism.

Provide the major organic product(s) when benzene is treated with the following sequence of reagents: 1. Br₂, FeBr₃2. HNO₃, H₂SO₄.

Rank the following compounds in order of increasing reactivity towards chlorination with Cl₂/AlCl₃ (slowest reacting to fastest).

Which of the following compounds will undergo bromination most rapidly using Br₂, FeBr₃?