
Concept explainers
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
To state and explain:
Whether ethyl chloride is expected to undergo Friedal- Crafts reaction with or without rearrangement.
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.
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.
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.
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.

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Chapter 16 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
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