Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed. Concept introduction: The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are, Formation of an enamine Michael addition Hydrolysis

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Answer 1

Question

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

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Answer 2

Question

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

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Answer 3

Question

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

Expert Solution & Answer

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Answer 4

Question

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

Expert Solution & Answer

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See solution

Answer 5

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

Answer 6

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

Answer 7

Chapter 21.7, Problem 42PTS

(a)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

Answer 8

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

Answer 9

(b)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

If the product is 1,3-difunctionalized means either it has to prepared via Aldol addition or Claisen condensation reaction.

Williamson ether synthesis is the synthesis of ether when alkoxide reacts with an alkyl halide.

Answer 10

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Using cyclopentanone as a starting material, synthesis of given compounds need to be proposed.

Concept introduction:

The addition of an enamine to α,β -unsaturated carbonyl acceptor (Michael acceptor) to form dicarbonyl compound is known as Stork enamine synthesis. The difference between Michael addition and stork enamine is that for Michael addition to take place the enolate formed should be doubly stabilized. The product is then hydrolyzed by an aqueous acid to produce 1,5-dicarbonyl compound. Steps involved in Stork enamine synthesis are,

Formation of an enamine

Michael addition

Hydrolysis

The formed 1,5-dicarbonyl compound undergoes reduction when treated with LAH to give 1,5-dihydroxy compound.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - Prob. 5ATS Ch. 21.1 - Prob. 6CC Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions