The structure of compounds A-H in the given synthesis is to be determined. Concept introduction: The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone . The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Question

Want to see the full answer?

Answer 1

Question

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 2

Question

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Answer 6

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Answer 7

Chapter 23, Problem 23.91P

Interpretation Introduction

Interpretation:

The structure of compounds A-H in the given synthesis is to be determined.

Concept introduction:

The synthesis of monoacylated product is formed in the electrophilic aromatic substitution from acyl chloride and arenes. Here, Friedel-Craft acylation occurs to form the ketone. The ketone is reduced to the isopentyl benzene. The alkyl group is an ortho/para director, and owing to sterics, nitration occurs primarily at the para position. The amine is formed when nitro group is reduced. which is then transformed into the diazonium ion. which reacts with CuCN to form the nitrile. The nitrile undergoes a Grignard reaction to form the ketone, which is reduced to the secondary alcohol.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 23 - Prob. 23.1P Ch. 23 - Prob. 23.2P Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Prob. 23.5P Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Want to see the full answer?

Chapter 23 Solutions