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.

When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, synthesize the following aldehydes beginning with an organic molecule containing three carbons or fewer.

(d)

Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any ­organic compound that has no more than four carbons:

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

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

1. 1-pentyn-3-ol

How could the following compounds be synthesized from acetylene?

b.

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)