Muscalure, the sex attractant of the common housefly, is cis-tricos-9-ene. Most syntheses of alkenes give the more stable trans isomer as the major product. Devise a synthesis of muscalure from acetylene and other compounds of your choice. Your synthesis must give specifically the cis isomer of muscalure.

How could the following compounds be synthesized from acetylene?

e.

The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.

Show how you would convert

d. but-1-yne to cis-hex-3-ene.

Show how you would synthesize the following compounds from acetylene and any other needed reagents:

(a) 6-phenylhex-1-en-4-yne

(b) cis-1-phenylpent-2-ene

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

d.

Propose structures for intermediates and products (F) through (G)

Beginning with acetylene and benzyl bromide and using any other inorganic reagents, propose a synthesis of the alkene shown here.

Show how the following compounds can be synthesized starting with ethyne:

a. cis-2-octene