Chapter 23.10, Problem 16P

Interpretation Introduction

a) 2-cyclohexanone

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with 2-cyclohexanone (α, β- unsaturated acceptor).

Interpretation Introduction

b) Propenenitrile

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with propenenitrile (α, β- unsaturated acceptor).

Interpretation Introduction

c) Ethyl-2-butenoate

Interpretation:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor) is to be given.

Concept introduction:

Michael reaction involves the conjugate addition of a stable enolate ion derived from a β-ketoesters or β- diketones or β- ketonitriles or malonic esters (donors) to an unhindered α,β- unsaturated ketones or aldehydes or esters or thioesters or nitriles or amides or nitro compounds (acceptors). The enolate ion from the donor attacks the double bond in acceptor. A new bond is formed between the α-carbon of the donor and the β- carbon of the unsaturated ester.

To give:

The product obtained in the base catalyzed Michael reaction of 2, 4-pentanedione with ethyl-2-butenoate (α, β- unsaturated acceptor).