Chapter 16, Problem 16.23P

Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each haloalkane with triphenylphosphine, (2) the phosphonium ylide formed by treatment of each phosphonium salt with butyllithium, and (3) the alkene formed by treatment of each phosphonium ylide with acetone.

Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

Mechanism:

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

Mechanism:

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

Mechanism:

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

Mechanism:

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

Mechanism:

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,

Interpretation Introduction

Interpretation:

The structural formulas for the materials formed in the each steps in the Wittig reaction of  given reactant has to be drawn.

Concept introduction:

The functional group in the aldehydes and Ketones are carbonyl group.

Wittig reaction is a reaction in which a nucleophilic elimination occurs after nucleophilic addition reaction. In this reaction an aldehyde or ketone reacts with a triphenyl phosphonium ylide (Wittig reagent) to give an alkene and triphenylphosphine oxide.

The reaction can be represented as shown below,

Mechanism:

Explanation of Solution

Given halo compound is shown below, 1,2 and 3 in the questions are the important steps in Wittig reaction.

When treating this compound with triphenylphosphine corresponding alkyltriphenylphosphonium salt will form.

Thus, the alkyltriphenylphosphonium salt formed in the reaction (1) can be drawn as follows,

Phosphonium ylide formed by treatment of this phosphonium salt with butyl lithium (2) can be drawn as shown below,

(3) The alkene formed by treatment of this phosphonium ylide with acetone is drawn below,