Reagents used for the transformation of cyclohexanone into the products given need to be identified. Concept introduction: Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance. Deprotonation of α carbon to form enolate Nucleophilic attack of enolate S N 2 reaction with alkyl halide

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Answer 1

Question

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

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Answer 2

Question

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Expert Solution & Answer

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Answer 3

Question

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Expert Solution & Answer

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See solution

Answer 4

Question

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Expert Solution & Answer

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See solution

Answer 5

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 6

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

Answer 7

Chapter 22, Problem 89PP

(a)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

S_N2 reaction with alkyl halide

Answer 8

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

Answer 9

(b)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

Answer 10

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

Answer 11

(c)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

When a ketone is deprotonated to form a resonance stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α, β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. A general scheme is shown below,

Answer 12

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 13

(d)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 14

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 15

(e)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 16

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 17

(f)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 18

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 19

(g)

Interpretation Introduction

Interpretation:

Reagents used for the transformation of cyclohexanone into the products given need to be identified.

Concept introduction:

Retrosynthetic approach is a method used to find the starting material from the structure of product by breaking it into simpler fragments and deducing a route for synthesis of the simpler fragments step by step to give the required product.

Change in carbon-carbon framework

Position of functional group.

Answer 20

Expert Solution & Answer

Answer 21

Expert Solution & Answer

Answer 22

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Answer 23

Ch. 22.1 - Prob. 1CC Ch. 22.1 - Prob. 2CC Ch. 22.1 - Prob. 3CC Ch. 22.1 - Prob. 1LTS Ch. 22.1 - Prob. 4PTS Ch. 22.1 - Prob. 5ATS Ch. 22.1 - Prob. 6CC Ch. 22.1 - Prob. 7CC Ch. 22.1 - Prob. 8CC Ch. 22.2 - Prob. 9CC

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Chapter 22 Solutions