Question 1

Provide the structures of the major organic products of the following reaction.

Accepted Answer

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

Question 2

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 3

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 4

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 5

Electrophilic iodination of benzene requires which reagent in addition to I2?

Accepted Answer

Question 6

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

Accepted Answer

1) CH₃CH₂CH₂C

Question 7

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 8

What sequence of reagents is needed to convert benzene into m-bromoethylbenzene?

Accepted Answer

1) CH₃COCl,

Question 9

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 10

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 11

Which step in an electrophilic aromatic substitution reaction is typically rate determining, formation of the sigma complex or loss of H+ by the sigma complex to form the product? Explain.

Accepted Answer

Formation of the sigma complex is typica

Question 12

Provide a detailed, stepwise mechanism for the following reaction.

Accepted Answer

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

Question 13

Provide the structures of the major organic products of the following reaction.

Accepted Answer

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

Question 14

Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions:

-Br.

Accepted Answer

-Br < -CH₂C

Question 15

Draw the four major resonance structures of the intermediate which results when   
is treated with NaOH.

Accepted Answer

The answer of Draw the four major resonance structures of...

Question 16

Provide the major organic product of the following reaction.

Accepted Answer

No reaction. Friedel-Crafts al

Question 17

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 18

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

Accepted Answer

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

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

In electrophilic aromatic substitution reactions, the -CF3 group is ________.

Accepted Answer

A)  an activating group because it donates electron density through inductive stabilization 
B)  an activating group because it donates electron density through resonance 
C)  a deactivating group because it withdraws electron density through inductive destabilization 
D)  a deactivating group because it withdraws electron density through resonance 
A)  an activating group because it donates electron density through inductive stabilization 
B)  an activating group because it donates electron density through resonance 
C)  a deactivating group because it withdraws electron density through inductive destabilization 
D)  a deactivating group because it withdraws electron density through resonance

Exam 17: Reactions of Aromatic Compounds

Provide the structures of the major organic products of the following reaction.

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

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

Electrophilic iodination of benzene requires which reagent in addition to I2?

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

Complete the following reaction by filling in the necessary reagents.

What sequence of reagents is needed to convert benzene into m-bromoethylbenzene?

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

The nitration of anisole ________.

Which step in an electrophilic aromatic substitution reaction is typically rate determining, formation of the sigma complex or loss of H+ by the sigma complex to form the product? Explain.

Provide a detailed, stepwise mechanism for the following reaction.

Provide the structures of the major organic products of the following reaction.

Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions: -Br.

Draw the four major resonance structures of the intermediate which results when is treated with NaOH.

Provide the major organic product of the following reaction.

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

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

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

In electrophilic aromatic substitution reactions, the -CF3 group is ________.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

Electrophilic iodination of benzene requires which reagent in addition to I₂?

Which step in an electrophilic aromatic substitution reaction is typically rate determining, formation of the sigma complex or loss of H⁺ by the sigma complex to form the product? Explain.

In electrophilic aromatic substitution reactions, the -CF₃ group is ________.