Question 1

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. CH₃CH₂Cl/AlCl₃ 2. HN

Question 2

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. fuming

Question 3

Cyclohexene undergoes addition reaction with bromine, but benzene does not. Instead benzene undergoes a substitution reaction with bromine. Explain why.

Accepted Answer

Cyclohexene has localized  @#LAT-DLM&electrons, wh

Question 4

Provide all the resonance structures of the sigma complex, when benzene reacts with an electrophile (E+).

Accepted Answer

Question 5

The following reaction will occur via which mechanism?

Accepted Answer

A)  elimination -addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  addition-elimination 
E)  both B & C 
A)  elimination -addition 
B)  nucleophilic aromatic substitution 
C)  electrophilic aromatic substitution 
D)  addition-elimination 
E)  both B & C

Question 6

Predict the major product for the following reaction.

Accepted Answer

The answer of Predict the major product for the following...

Question 7

Which of the following substituents will direct the incoming group in the ortho/para position during electrophilic aromatic substitution?

Accepted Answer

A)  -CH2CH3 
B)  -CF3 
C)  -OCH3 
D)  -COOCH3 
E)  both A & C 
A)  -CH2CH3 
B)  -CF3 
C)  -OCH3 
D)  -COOCH3 
E)  both A & C

Question 8

Predict the major product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Question 9

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 10

Predict the product and provide a stepwise curved arrow mechanism for the following reaction.

Accepted Answer

The answer of Predict the product and provide a stepwise...

Question 11

Provide a stepwise curved arrow mechanism for chlorination of benzene in the presence of FeCl3.

Accepted Answer

Question 12

Predict the major product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  I & II 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  I & II

Question 13

Which of these is the rate-determining step in the electrophilic aromatic substitution of benzene?

Accepted Answer

A)  Formation of an electrophile 
B)  Formation of sigma complex. 
C)  Loss of proton from sigma complex. 
D)  Addition of electrophile & loss of proton 
E)  None of these 
A)  Formation of an electrophile 
B)  Formation of sigma complex. 
C)  Loss of proton from sigma complex. 
D)  Addition of electrophile & loss of proton 
E)  None of these

Question 14

Which one of the following compounds would be most reactive toward electrophilic aromatic substitution?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 15

Starting with benzene propose a stepwise synthesis for the following compound.

Accepted Answer

The answer of Starting with benzene propose a stepwise synthesis...

Question 16

Provide the structures of major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position.

Accepted Answer

The answer of Provide the structures of major resonance contributors...

Question 17

Predict the major product for the following reaction.

Accepted Answer

The answer of Predict the major product for the following...

Question 18

Provide a stepwise curved arrow mechanism for the following reaction.

Accepted Answer

The answer of Provide a stepwise curved arrow mechanism for...

Question 19

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.

Accepted Answer

A)  chlorobenzene 
B)  sec-butylbenzene 
C)  ethylbenzene 
D)  isopropylbenzene 
E)  t-butylbenzene 
A)  chlorobenzene 
B)  sec-butylbenzene 
C)  ethylbenzene 
D)  isopropylbenzene 
E)  t-butylbenzene

Question 20

Predict the product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Exam 19: Aromatic Substitution Reactions

Provide the reagents necessary to carry out the following conversion.

Provide the reagents necessary to carry out the following conversion.

Cyclohexene undergoes addition reaction with bromine, but benzene does not. Instead benzene undergoes a substitution reaction with bromine. Explain why.

Provide all the resonance structures of the sigma complex, when benzene reacts with an electrophile (E+).

The following reaction will occur via which mechanism?

Predict the major product for the following reaction.

Which of the following substituents will direct the incoming group in the ortho/para position during electrophilic aromatic substitution?

Predict the major product for the following reaction.

Predict the product for the following reaction.

Predict the product and provide a stepwise curved arrow mechanism for the following reaction.

Provide a stepwise curved arrow mechanism for chlorination of benzene in the presence of FeCl3.

Predict the major product for the following reaction.

Which of these is the rate-determining step in the electrophilic aromatic substitution of benzene?

Which one of the following compounds would be most reactive toward electrophilic aromatic substitution?

Starting with benzene propose a stepwise synthesis for the following compound.

Provide the structures of major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position.

Predict the major product for the following reaction.

Provide a stepwise curved arrow mechanism for the following reaction.

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.

Predict the product for the following reaction.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Substitution Reactions

Alkenes: Structure and Preparation Via Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide all the resonance structures of the sigma complex, when benzene reacts with an electrophile (E⁺).

Provide a stepwise curved arrow mechanism for chlorination of benzene in the presence of FeCl₃.

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl₃.