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 AlCl 3 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.

Question

Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R H

Answer 1

Question

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.

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Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R H

Calculate the proton and carbon chemical shifts for this structure

A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?

Answer 2

Question

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.

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Answer 3

Question

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.

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Answer 4

Question

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.

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Answer 5

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.

Answer 6

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.

Answer 7

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.

Answer 8

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.

Answer 9

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.

Answer 10

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.

Answer 11

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.

Answer 12

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.

Answer 13

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.

Answer 14

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.

Answer 15

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.

Answer 16

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Answer 27

Ch. 16.1 - Prob. 1P Ch. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SÅª4. deuterium...Ch. 16.3 - Prob. 5P Ch. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P

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Chapter 16 Solutions