Question 1

The nitration of anisole:

Accepted Answer

A)  proceeds more rapidly than the nitration of benzene and yields predominantly the meta product. 
B)  proceeds more rapidly than the nitration of benzene and yields predominantly the ortho, para products. 
C)  proceeds more slowly than the nitration of benzene and yields predominantly the meta product. 
D)  proceeds more slowly than the nitration of benzene and yields predominantly the ortho, para products. 
E)  proceeds at the same rate as the nitration of benzene and yields predominantly the meta product. 
A)  proceeds more rapidly than the nitration of benzene and yields predominantly the meta product. 
B)  proceeds more rapidly than the nitration of benzene and yields predominantly the ortho, para products. 
C)  proceeds more slowly than the nitration of benzene and yields predominantly the meta product. 
D)  proceeds more slowly than the nitration of benzene and yields predominantly the ortho, para products. 
E)  proceeds at the same rate as the nitration of benzene and yields predominantly the meta product.

Question 2

Draw the four major resonance structures of the sigma complex intermediate in the reaction of anisole with HNO3/H2SO4 to yield p-nitroanisole.

Accepted Answer

Question 3

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 4

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 5

In electrophilic aromatic substitution reactions, a -NHCOCH3 substituent on the aromatic ring is:

Accepted Answer

A)  a deactivator and a m-director. 
B)  a deactivator and an o,p-director. 
C)  an activator and a m-director. 
D)  an activator and an o,p-director. 
E)  none of the above. 
A)  a deactivator and a m-director. 
B)  a deactivator and an o,p-director. 
C)  an activator and a m-director. 
D)  an activator and an o,p-director. 
E)  none of the above.

Question 6

Provide the structure of the major organic product in the following reaction sequence.

Accepted Answer

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

Question 7

Predict the major organic product resulting from the following sequence of reactions.

Accepted Answer

The answer of Predict the major organic product resulting from...

Question 8

Which of the following is an incorrect statement about the bromination of benzene by Br2 and FeBr3?

Accepted Answer

A)  FeBr3 functions to increase the electrophilicity of Br2. 
B)  Formation of the sigma complex is the rate-determining step of the mechanism. 
C)  The carbanionic intermediate is resonance stabilized. 
D)  There are two carbon-containing intermediates in the mechanism. 
E)  The final step of the mechanism is loss of H+. 
A)  FeBr3 functions to increase the electrophilicity of Br2. 
B)  Formation of the sigma complex is the rate-determining step of the mechanism. 
C)  The carbanionic intermediate is resonance stabilized. 
D)  There are two carbon-containing intermediates in the mechanism. 
E)  The final step of the mechanism is loss of H+.

Question 9

Provide the structure of the major organic product in the following reaction.

Accepted Answer

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

Question 10

Which of the following compounds will undergo bromination least rapidly when treated with Br2 and FeBr3?

Accepted Answer

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

Question 11

Derivatives of the compound shown below are currently being examined for their effectiveness in treating drug addiction and metabolic syndrome (J. Med. Chem. 2006, 872). Which sequence ranks the following aromatic rings of this compound in order of increasing reactivity in an electrophilic aromatic substitution reaction (slowest to fastest reacting)?

Accepted Answer

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

Question 12

Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene.

Accepted Answer

1. CH₃COCl,

Question 13

Under what reaction conditions does the electrophilic chlorination of aromatic compounds usually occur?

Accepted Answer

A)  Cl2, AlCl3 
B)  Cl2, H2O 
C)  Cl2, CCl4 
D)  NaCl, H2O 
E)  NaCl, CH3OH 
A)  Cl2, AlCl3 
B)  Cl2, H2O 
C)  Cl2, CCl4 
D)  NaCl, H2O 
E)  NaCl, CH3OH

Question 14

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 15

Which of the following compounds would most likely be used in the preparation of isobutylbenzene from benzene?

Accepted Answer

A)  (CH3)2CHCOCl 
B)  (CH3)2CHCH2Cl 
C)  (CH3)2CHCH2Br 
D)  CH3CH2CH2CH2Cl 
E)  CH3CH2CH2COCl 
A)  (CH3)2CHCOCl 
B)  (CH3)2CHCH2Cl 
C)  (CH3)2CHCH2Br 
D)  CH3CH2CH2CH2Cl 
E)  CH3CH2CH2COCl

Question 16

Provide the structure of the major organic product in the following reaction

Accepted Answer

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

Question 17

Provide the major organic product(s) of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 18

Provide the structure of the major monoitration product of the compound below.

Accepted Answer

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

Question 19

Provide the major organic product(s) of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 20

Provide a series of synthetic steps by which p-nitrophenol can be prepared from benzene.

Accepted Answer

1. Cl₂, AlC

Exam 17: Reactions of Aromatic Compounds

The nitration of anisole:

Draw the four major resonance structures of the sigma complex intermediate in the reaction of anisole with HNO3/H2SO4 to yield p-nitroanisole.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

In electrophilic aromatic substitution reactions, a -NHCOCH3 substituent on the aromatic ring is:

Provide the structure of the major organic product in the following reaction sequence.

Predict the major organic product resulting from the following sequence of reactions.

Which of the following is an incorrect statement about the bromination of benzene by Br2 and FeBr3?

Provide the structure of the major organic product in the following reaction.

Which of the following compounds will undergo bromination least rapidly when treated with Br2 and FeBr3?

Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene.

Under what reaction conditions does the electrophilic chlorination of aromatic compounds usually occur?

Provide the major organic product of the following reaction.

Which of the following compounds would most likely be used in the preparation of isobutylbenzene from benzene?

Provide the structure of the major organic product in the following reaction

Provide the major organic product(s) of the reaction shown below.

Provide the structure of the major monoitration product of the compound below.

Provide the major organic product(s) of the reaction shown below.

Provide a series of synthetic steps by which p-nitrophenol can be prepared from benzene.

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

Draw the four major resonance structures of the sigma complex intermediate in the reaction of anisole with HNO₃/H₂SO₄ to yield p-nitroanisole.

In electrophilic aromatic substitution reactions, a -NHCOCH₃ substituent on the aromatic ring is:

Which of the following is an incorrect statement about the bromination of benzene by Br₂ and FeBr₃?

Which of the following compounds will undergo bromination least rapidly when treated with Br₂ and FeBr₃?