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.

How can the following compounds be prepared using ethyne as the starting material?

b.

How could the following compounds be synthesized from acetylene?

c. CH₃CH═CH₂

How could the following compounds be synthesized from acetylene?

d.

How could the following compounds be synthesized from acetylene?

e.

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

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.

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

d.