Question 1

Which of the following is the strongest activating group in electrophilic aromatic substitution reactions?

Accepted Answer

A)  -CH2CH3 
B)  -OCH3 
C)  -CO2CH3 
D)  -NO2 
E)  -N(CH3)2 
A)  -CH2CH3 
B)  -OCH3 
C)  -CO2CH3 
D)  -NO2 
E)  -N(CH3)2

Question 2

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 3

Provide a series of synthetic steps by which 4-t-butylbenzoic acid can be prepared from toluene.

Accepted Answer

1. (CH₃)₃CCl

Question 4

Provide the structure of the major organic product(s) in the following reaction.

Accepted Answer

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

Question 5

Draw the two major resonance structures of the acylium ion which results when butanoyl chloride   is treated with AlCl3.

Accepted Answer

Question 6

What intermediate is thought to occur in the elimination-addition nucleophilic aromatic substitution mechanism?

Accepted Answer

A)  radical anion 
B)  radical cation 
C)  quinone 
D)  benzyne 
E)  positively charged sigma complex 
A)  radical anion 
B)  radical cation 
C)  quinone 
D)  benzyne 
E)  positively charged sigma complex

Question 7

List two of the three limitations usually associated with the Friedel-Crafts alkylation reaction.

Accepted Answer

1. Reaction fails when strongl

Question 8

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 9

Which of the following compounds is least reactive in the nucleophilic aromatic substitution reaction with NaOH?

Accepted Answer

A)  2,4-dinitrochlorobenzene 
B)  m-nitrochlorobenzene 
C)  o-nitrochlorobenzene 
D)  p-nitrochlorobenzene 
E)  3,5-dinitrochlorobenzene 
A)  2,4-dinitrochlorobenzene 
B)  m-nitrochlorobenzene 
C)  o-nitrochlorobenzene 
D)  p-nitrochlorobenzene 
E)  3,5-dinitrochlorobenzene

Question 10

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 11

In electrophilic aromatic substitution reactions the nitro group is:

Accepted Answer

A)  a m-director since it destabilizes the meta sigma complex more than the ortho, para. 
B)  a m-director since it destabilizes the meta sigma complex less than the ortho, para. 
C)  an o,p-director since it stabilizes the ortho, para sigma complex more than the meta. 
D)  an o,p-director since it stabilizes the ortho, para sigma complex less than the meta. 
E)  none of the above. 
A)  a m-director since it destabilizes the meta sigma complex more than the ortho, para. 
B)  a m-director since it destabilizes the meta sigma complex less than the ortho, para. 
C)  an o,p-director since it stabilizes the ortho, para sigma complex more than the meta. 
D)  an o,p-director since it stabilizes the ortho, para sigma complex less than the meta. 
E)  none of the above.

Question 12

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 13

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

Accepted Answer

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

Question 14

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 15

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 16

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 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 a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

Accepted Answer

1. HNO₃, H₂S

Question 19

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

Accepted Answer

Question 20

Which of the following compounds will react most rapidly when treated with CH3CH2Cl and AlCl3?

Accepted Answer

A)  benzene 
B)  chlorobenzene 
C)  nitrobenzene 
D)  anisole 
E)  toluene 
A)  benzene 
B)  chlorobenzene 
C)  nitrobenzene 
D)  anisole 
E)  toluene

Exam 17: Reactions of Aromatic Compounds

Which of the following is the strongest activating group in electrophilic aromatic substitution reactions?

Provide the major organic product of the following reaction.

Provide a series of synthetic steps by which 4-t-butylbenzoic acid can be prepared from toluene.

Provide the structure of the major organic product(s) in the following reaction.

Draw the two major resonance structures of the acylium ion which results when butanoyl chloride is treated with AlCl3.

What intermediate is thought to occur in the elimination-addition nucleophilic aromatic substitution mechanism?

List two of the three limitations usually associated with the Friedel-Crafts alkylation reaction.

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

Which of the following compounds is least reactive in the nucleophilic aromatic substitution reaction with NaOH?

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

In electrophilic aromatic substitution reactions the nitro group is:

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

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

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

Provide the major organic product of the following reaction.

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

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

Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

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

Which of the following compounds will react most rapidly when treated with CH3CH2Cl and AlCl3?

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

Whichof the following is the strongest activating group in electrophilic aromatic substitution reactions?

Draw the two major resonance structures of the acylium ion which results when butanoyl chloride is treated with AlCl₃.

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

Which of the following compounds will react most rapidly when treated with CH₃CH₂Cl and AlCl₃?