14. Synthetic Techniques

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

2. 1-phenyl-2-butyn-1-ol

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

b.

Propose a synthesis:

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.

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

(b)

Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are two correct answers for each product.]

(c)

Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents

(a)

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

1. 1-pentyn-3-ol

Propose a synthesis:

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

d.

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

c.

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.

(c)

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 you would accomplish the following syntheses. You may use whatever additional reagents you need.

(f)