14. Synthetic Techniques

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

(f)

Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.

(d)

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 you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

g. pentanal, CH₃CH₂CH₂CH₂CHO

h. pentan-2-one, CH₃–CO–CH₂CH₂CH₃

i. (±) 3,4-dibromohexane

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

c.

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

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)

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

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

How could the following compounds be synthesized from acetylene?

b.