The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction. Interpretation: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction is to be shown. Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

Question

Propose a mechanism for the following reaction. a. Explain why two products are formed. b. Explain why methanol substitutes for only one of the bromines

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.59SP

(a)

Interpretation Introduction

To explain: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction.

Interpretation: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction is to be shown.

Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

(b)

Interpretation Introduction

To determine: The transformation of cyclohexanone to methylenecyclohexane without using a Wittig reaction and an explanation corresponding to Wittig reaction being a much better synthesis.

Interpretation: The transformation of cyclohexanone to methylenecyclohexane without using a Wittig reaction and an explanation corresponding to Wittig reaction being a much better synthesis is to be stated.

Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

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Propose a mechanism for the following reaction. a. Explain why two products are formed. b. Explain why methanol substitutes for only one of the bromines

a. Draw the structures of all the elimination products. b. The reaction occurs through an E2 mechanism. Using one of your products writethe mechanism of the reaction using curved arrows. c. Is this reaction regioselective? Explain your answer. d. Explain why the reaction is stereoselective.

2. Propose reagents that would affect the following transformations. Pay attention to the order of addition. C. a. b. Br Br NO₂

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.59SP

(a)

Interpretation Introduction

To explain: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction.

Interpretation: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction is to be shown.

Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

(b)

Interpretation Introduction

To determine: The transformation of cyclohexanone to methylenecyclohexane without using a Wittig reaction and an explanation corresponding to Wittig reaction being a much better synthesis.

Interpretation: The transformation of cyclohexanone to methylenecyclohexane without using a Wittig reaction and an explanation corresponding to Wittig reaction being a much better synthesis is to be stated.

Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

Expert Solution & Answer

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Check out sample textbook solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.59SP

(a)

Interpretation Introduction

To explain: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction.

Interpretation: The transformation of cyclohexanone to methylenecyclohexane using a Wittig reaction is to be shown.

Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

(b)

Interpretation Introduction

To determine: The transformation of cyclohexanone to methylenecyclohexane without using a Wittig reaction and an explanation corresponding to Wittig reaction being a much better synthesis.

Interpretation: The transformation of cyclohexanone to methylenecyclohexane without using a Wittig reaction and an explanation corresponding to Wittig reaction being a much better synthesis is to be stated.

Concept introduction: The reaction of an aldehyde or ketone and phosphorous ylide to form an alkene is known as Wittig reaction. The Wittig reaction is useful for placing double bonds in less stable positions.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 18, Problem 18.59SP

(a)

Interpretation Introduction