The structural formula for the betaine formed by the reaction of methylenetriphenylphosphorane with cyclohexanone is to be drawn. The conversion of the betaine to an oxaphosphetane is to be shown using curved arrows. Also, the one-step conversion of the betaine to methylenecyclohexane and triphenylphosphine oxide is to be shown using curved arrows. Concept introduction: The reaction of an aldehyde or a ketone with triphenylphosphonium ylide results in the formation of an alkene as the final product. This reaction is commonly known as Wittig reaction. In the first step of the reaction, the nucleophilic attack of the ylide on the carbonyl carbon takes place to form betaine. In the second step, the formation of the four-membered ring, oxaphosphetane occurs and in the final step, the alkene is formed as a product.

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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 18.12, Problem 21P

Interpretation Introduction

Interpretation:

The structural formula for the betaine formed by the reaction of methylenetriphenylphosphorane with cyclohexanone is to be drawn. The conversion of the betaine to an oxaphosphetane is to be shown using curved arrows. Also, the one-step conversion of the betaine to methylenecyclohexane and triphenylphosphine oxide is to be shown using curved arrows.

Concept introduction:

The reaction of an aldehyde or a ketone with triphenylphosphonium ylide results in the formation of an alkene as the final product.

This reaction is commonly known as Wittig reaction.

In the first step of the reaction, the nucleophilic attack of the ylide on the carbonyl carbon takes place to form betaine.

In the second step, the formation of the four-membered ring, oxaphosphetane occurs and in the final step, the alkene is formed as a product.

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In the box below, specify which of the given compounds are very soluble in polar aprotic solvents. You may select more than one compound. Choose one or more: NaCl NH4Cl CH3CH2CH2CH2CH2CN CH3CH2OH hexan-2-one NaOH CH3SCH3

On the following structure, select all of the atoms that could ACCEPT a hydrogen bond. Ignore possible complications of aromaticity. When selecting be sure to click on the center of the atom.

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 18.12, Problem 21P

Interpretation Introduction

Interpretation:

The structural formula for the betaine formed by the reaction of methylenetriphenylphosphorane with cyclohexanone is to be drawn. The conversion of the betaine to an oxaphosphetane is to be shown using curved arrows. Also, the one-step conversion of the betaine to methylenecyclohexane and triphenylphosphine oxide is to be shown using curved arrows.

Concept introduction:

The reaction of an aldehyde or a ketone with triphenylphosphonium ylide results in the formation of an alkene as the final product.

This reaction is commonly known as Wittig reaction.

In the first step of the reaction, the nucleophilic attack of the ylide on the carbonyl carbon takes place to form betaine.

In the second step, the formation of the four-membered ring, oxaphosphetane occurs and in the final step, the alkene is formed as a product.

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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 18.12, Problem 21P

Interpretation Introduction

Interpretation:

The structural formula for the betaine formed by the reaction of methylenetriphenylphosphorane with cyclohexanone is to be drawn. The conversion of the betaine to an oxaphosphetane is to be shown using curved arrows. Also, the one-step conversion of the betaine to methylenecyclohexane and triphenylphosphine oxide is to be shown using curved arrows.

Concept introduction:

The reaction of an aldehyde or a ketone with triphenylphosphonium ylide results in the formation of an alkene as the final product.

This reaction is commonly known as Wittig reaction.

In the first step of the reaction, the nucleophilic attack of the ylide on the carbonyl carbon takes place to form betaine.

In the second step, the formation of the four-membered ring, oxaphosphetane occurs and in the final step, the alkene is formed as a product.

Expert Solution & Answer

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Check out a sample textbook solution

See 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 18.12, Problem 21P

Interpretation Introduction