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  1. Question:β -Vetivone is isolated from vetiver, a perennial grass that yields a variety of compounds usedin traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular 00a00000ldol reaction.000 (a) What Michael acceptor is needed for the conjugate addition? (See Problem23.61 for another method to form the bicyclic ring system of β-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.

Short Answer

Expert verified

Answer

a. Michael acceptor:

b.

Step by step solution

01

Michael reaction

In Michael reaction, an α,β-unsaturated ketone is subjected to 1,4-addition with an enolate. The enolate acts as a nucleophile that gets deprotonate in presence of ethoxide, and then attacks at the β-carbon position of the ketone system.

The general reaction is given below:

Michael Reaction

02

Aldol condensation

When two carbonyl compounds react in the presence of a strong base to form an α,β-unsaturated ketone or aldehyde, the reaction is known as Aldol condensation. The reaction proceeds with the formation of enol or enolate.

The general reaction is given below:

Aldol condensation

03

Determination of Michael acceptor

In Michael reaction, theα,β-unsaturated ketone is termed as the Michael acceptor.

For the given compound, the Michael acceptor would be:

Determination of Michael acceptor

04

Mechanism of Aldol condensation

The mechanism of aldol condensation of β-vetivone is given below:

Mechanism of the Aldol condensation step

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