Draw the product of each of the following reactions:
1.

Show the products of the following acetylide alkylation reactions. [Make sure your product has the correct number of carbons.]

(b)

Calculate for the following acid–base reactions. Which is the best base to use to deprotonate acetylene and make the acetylide anion?

(c)

Suggest reagents you might use to generate the product from the given reactant.

(b)

A chemist is planning to synthesize 3-octyne by adding 1-bromobutane to the product obtained from the reaction of 1-butyne with sodium amide. Unfortunately, however, he forgot to order 1-butyne. How else can he prepare 3-octyne?

Show how you might synthesize the following compounds, using acetylene and any ­suitable alkyl halides as your starting materials. If the compound given cannot be ­synthesized by this method, explain why.

d. 4-methylhex-2-yne

e. 5-methylhex-2-yne

f. cyclodecyne

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

3. 2-methyl-3-hexyn-2-ol

Why is a cumulated diene not formed in the reaction shown above?

A chemist attempted to do the following acetylide alkylation reaction but was unsuccessful in several attempts, producing only the original starting materials in each case. Explain why the reaction didn't work.