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Chapter 18: Q18-64E (page 594)

How would you synthesize racemic disparlure (Problem 18-63) from compounds having ten or fewer carbons?

Short Answer

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Step by step solution

01

Step-by-step Solution

The Disparlure, is a sex attractant released by the female gypsy moth called Lymantria dispar.

Reaction of disparlure with acid and then with potassium permanganate yields two carboxylic acids gives undecanoic acid and 6-methyl- heptanoic acid.

02

Explanation

The reaction for the synthesis of racemic Displature is shown below.

The compound can be synthesized starting from the 7-methyl octane. It is oxidised using sodium hydrazine, followed by nucleophilic substitution reaction with bromodecane. The triple bond is reduced to cis- alkene using the Lindlars catalyst. The obtained alkene on epoxidation with peroxide gives the racemic mixture of Displature.

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Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

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