How could the following compounds be synthesized from acetylene?
b.

Show how each of the following compounds can be synthesized from the given starting materials:

d.

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.

(d) cyclohexanone

(e) CH₃CH₂CH₂CHO

The application box in the margin of states, “The addition of an acetylide ion to a carbonyl group is used in the synthesis of ethchlorvynol, a drug used to cause drowsiness and induce sleep.” Show how you would accomplish this synthesis from acetylene and a carbonyl compound.

Show how the following compounds can be prepared, using ethyne as one of the starting materials:

1. 1-pentyn-3-ol

Reaction of the acetylide with the epoxide shown will not form the desired product. What side reaction occurs instead? Why?

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.

(b)

Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(b)

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(b)