The sex attractant given off by the common housefly is an...

The sex attractant given off by the common housefly is an alkene named muscalure. Propose a synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure?
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Key Concepts

IUPAC Nomenclature in Organic Chemistry

The systematic naming of organic molecules using IUPAC rules is fundamental to clear communication in chemistry. It involves identifying the longest carbon chain, the position and geometry of double bonds, and any substituents present in the molecule. This ensures that the structure is reported unambiguously, which is particularly important when naming bioactive compounds such as muscalure.

Deprotonation of Terminal Alkynes

Acetylene is a terminal alkyne with acidic hydrogen atoms that can be removed by a strong base to generate an acetylide anion. This reactive species is crucial for nucleophilic substitution reactions, enabling the formation of new carbon–carbon bonds by attacking suitable electrophilic centers such as alkyl halides.

SN2 Reactions in Carbon–Carbon Bond Formation

The acetylide anion generated from acetylene can participate in SN2 reactions with alkyl halides. This mechanism is a standard strategy for joining two carbon fragments together, allowing for the construction of more complex molecular frameworks from simple starting materials by displacing a leaving group.

Partial Hydrogenation of Alkynes to Alkenes

Once a substituted alkyne is formed via nucleophilic substitution, it can be partially hydrogenated to yield the corresponding alkene. Controlled hydrogenation, typically using a poisoned catalyst like Lindlar’s catalyst, is essential for achieving stereoselectivity, notably forming the Z-alkene when the geometry of the double bond is critical for the molecule’s biological activity.

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