a) Interpretation: How to prepare cyclohexene from 2-cyclohexenone is to be stated. Concept introduction: Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone. To state: How to prepare cyclohexene from 2-cyclohexenone.

Question

(racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehyde

Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

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(racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehyde

R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…

Provide the reasonable steps to achieve the following synthesis.

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

Expert Solution & Answer

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Answer 5

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

Answer 6

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Answer 7

Chapter 19.SE, Problem 62AP

Interpretation Introduction

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Answer 8

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Answer 9

Interpretation Introduction

b)

Interpretation:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone is to be stated.

Concept introduction:

By treating 2-cyclohexenone with lithiumdiphenylcopper and acidifying the product formed 3-phenylcyclohexanone can be prepared, as the organolithiumcopper reagents are good reagents for the conjugate addition to α,β- unsaturated ketones.

To state:

How to prepare 3-phenylcyclohexanone from 2-cyclohexenone.

Answer 10

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Answer 11

Interpretation Introduction

c)

Interpretation:

How to prepare the ketoacid shown from 2-cyclohexenone is to be stated.

Concept introduction:

An easily oxidizable group is introduced to C₃ of 2-cyclohexenone by a conjugate addition using lithiumdialkylcopper reagent. The resulting product can then be oxidized to a carboxylic acid by acidified KMnO₄.

To state:

How to prepare the keto acid shown from 2-cyclohexenone.

Answer 12

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

Answer 13

Interpretation Introduction

d)

Interpretation:

How to prepare methylcyclohexane from 2-cyclohexenone (two ways) is to be shown.

Concept introduction:

An alkyl group can be introduced into 2-cyclohexenone by treating it with lithiumdialkyl reagent(conjugate addition takes place). The keto group can be reduced to CH₂ by Wolff-Kishner reduction.

Another way is to replace the C =O in 2-cyclohexenone by C =CH₂ by a Wittig reaction first and then reducing it to C-CH₃ by H₂, Pd/C.

To state:

How to prepare methylcyclohexane from 2-cyclohexenone.

Answer 14

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Answer 19

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Answer 25

Ch. 19.1 - Prob. 1P Ch. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3P Ch. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7P Ch. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9P Ch. 19.8 - Show the products you would obtain by...

a) Interpretation: How to prepare cyclohexene from 2-cyclohexenone is to be stated. Concept introduction: Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone. To state: How to prepare cyclohexene from 2-cyclohexenone.

Solution Summary: The author explains how Wolf-Kishner reduction rection can be used to prepare cyclohexene.

a)

Interpretation:

How to prepare cyclohexene from 2-cyclohexenone is to be stated.

Concept introduction:

Wolf-Kishner reduction rection can be used to prepare cyclohexene from 2-cyclohexenone.

To state:

How to prepare cyclohexene from 2-cyclohexenone.

Chapter 19 Solutions