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Show how the following products might be synthesized from

Chapter 16, Problem 56P

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QUESTION:

Show how the following products might be synthesized from suitable Michael donors and

Acceptors.

Questions & Answers

QUESTION:

Show how the following products might be synthesized from suitable Michael donors and

Acceptors.

ANSWER:

Solution 56P

(a)

The given compound is shown below:

In Michael addition product, a new bond is formed at carbon atom. To obtain Michael acceptor and Michael donor, break the bond. This is shown below:

Synthesize the given compound is as follows:

In step-I, the nucleophile attacks at electrophilic carbon atom to form enolate ion.

In step-II, the enolate ion is protonated and followed by keto-enol tautomerization to form target product.

(b)

The given compound is shown below:

In Michael addition product, a new bond is formed at carbon atom. To obtain Michael acceptor and Michael donor, break the bond. This is shown below:

Synthesize the given compound is as follows:

In step-I, the nucleophile attacks at electrophilic carbon atom to form enolate ion and followed by protonation to form ethyl 2-acetyl-4-cyanobutanoate.

Ethyl 2-acetyl-4-cyanobutanoate undergoes hydrolysis and decarboxylation to form target product.

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