Chapter 16, Problem 89P

(a)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

(b)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

(c)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is:

(d)

Interpretation Introduction

Interpretation:

The carbonyl carbon and phosphonium ylide that are needed to synthesize the given compound has to be identified.

Concept introduction:

Wittig reaction:

Witting reaction is the reaction between the carbonyl carbon of aldehyde or ketone and the phosphonium ylide to give an alkene.  Wittig reaction is a very useful method to synthesize the compound which can’t be synthesis easily by other methods.

Specific phosphonium ylide can be prepared for specific alkene synthesis.  The triphenylphosphine is reacted with alkyl halide that has required numbers of carbon.  A strong base such as sodium hydride or butyllithium is added to remove proton of carbon adjacent to the phosphorus atom.  The carbon of prepared phosphonium ylide have nucleophilic character and get attached to the carbonyl carbon and carbonyl oxygen get attached to the positively charged phosphorous.  Triphenylphosphine oxide gets eliminated resulting in the formation of the alkene.

The mechanism of the witting reaction is: