Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn. Concept introduction: The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus. In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

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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 17, Problem 17.70P

Interpretation Introduction

Interpretation:

Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn.

Concept introduction:

The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus.

In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

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Answer 2

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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 17, Problem 17.70P

Interpretation Introduction

Interpretation:

Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn.

Concept introduction:

The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus.

In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

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Answer 3

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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 17, Problem 17.70P

Interpretation Introduction

Interpretation:

Detailed mechanism for the given reaction of an α,β- unsaturated ketone with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound is to be drawn.

Concept introduction:

The Wittig reaction is one of the primary methods of preparation of alkene from aldehyde or ketone using a reagent called ylide. The ylide is a neutral molecule having positively charged phosphorous atom bonded to negatively charged carbon atom. The negatively charged carbon of an ylide acts as a nucleophile and attacks the electrophilic carbon of carbonyl group and forms betaine, which has the negative charge on the oxygen and positive charge on the phosphorus atom. The reaction proceeds with the formation of four membered ring intermediate called an oxaphosphetane by forming a bond between the negatively charged oxygen and positively charged phosphorus.

In case of α,β- unsaturated ketone, the negatively charged carbon attacks the β carbon instead of the carbonyl carbon and forms the bicyclic compound.

Expert Solution & Answer

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Check out a sample textbook solution

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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 17, Problem 17.70P

Interpretation Introduction