Chapter 16.3, Problem 5P

Interpretation Introduction

a)

Interpretation:

Whether ethyl chloride is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.

Concept introduction:

Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl₃ to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift (particularly when a primary alkyl halide is used) can lead to the formation of rearranged products also in this reaction.

To state and explain:

Whether ethyl chloride is expected to undergo Friedal- Crafts reaction with or without rearrangement.

Interpretation Introduction

b)

Interpretation:

Whether 2-chlorobutane is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.

Concept introduction:

Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl₃ to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift (particularly when a primary alkyl halide is used) can lead to the formation of rearranged product also in this reaction.

To state and explain:

Whether 2-chlorobutane is expected to undergo Friedal-Crafts reaction with or without rearrangement.

Interpretation Introduction

c)

Interpretation:

Whether n-propyl chloride is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.

Concept introduction:

Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl₃ to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift, particularly when a primary alkyl halide is used, can lead to the formation of rearranged product also in this reaction.

To state and explain:

Whether n-propyl chloride is expected to undergo Friedal-Crafts reaction with or without rearrangement.

Interpretation Introduction

d)

Interpretation:

Whether 1-chloro-2, 2-dimethylpropane is expected to undergo Friedal-Crafts reaction with or without rearrangement is to be stated and explained.

Concept introduction:

Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl₃ to produce an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift, particularly when a primary alkyl halide is used, can lead to the formation of rearranged product also in this reaction.

To state and explain:

Whether 1-chloro-2, 2-dimethylpropane is expected to undergo Friedal-Crafts reaction with or without rearrangement.

Interpretation Introduction

e)

Interpretation:

Whether chlorocyclohexane is expected to undergo Friedal Crafts reaction with or without rearrangement is to be stated and explained.

Concept introduction:

Friedal-Crafts reaction is an electrophilic substitution reaction in which an aromatic compound reacts with an alkyl chloride in the presence of AlCl₃ to yield an alkylbenzene. The electrophile in this reaction is an alkyl carbocation. The skeletal rearrangement of the alkyl carbocation electrophile either through a hydride shift or alkyl shift, particularly when a primary alkyl halide is used, can lead to the formation of rearranged product also in this reaction.

To state and explain:

Whether chlorocyclohexane is expected to undergo Friedal-Crafts reaction with or without rearrangement.