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Chapter 12: Q.61. (page 492)

Question: Devise a synthesis of muscalure, the sex pheromone of the common housefly, from acetylene and any other required reagents.

Muscalure

Short Answer

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Answer:

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01

Deprotonation

The organic reaction in which a proton is removed from the compound with the help of a strong base such as sodium or potassium hydride is known as a deprotonation reaction.

The acetylene is deprotonated by the strong base sodium hydride to produce sodium acetylide.

Deprotonation of Acetylene

02

Substitution reaction

The strong base sodium acetylide would undergo a substitution reaction with bromononane to replace bromine with the acetylide anion.

Substitution reaction.

03

Deprotonation and substitution

This compound is again treated with another molecule of sodium hydride, followed by bromotridecane, to form a substituted alkyne.

Deprotonation followed by substitution

04

Reduction reaction

The corresponding alkyne is reduced with hydrogen in the presence of Lindlar鈥檚catalyst to form the cis alkene (Z)-9-tricosene.

Reduction of alkyne to alkene

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