10. Addition Reactions

Show how you would accomplish the following synthetic transformations. Show all intermediates.

h. hex-1-yne → hexan-2-one, CH₃COCH₂CH₂CH₂CH₃

What are products of the following reactions?

f.

When pent-2-yne reacts with mercuric sulfate in dilute sulfuric acid, the product is a mixture of two ketones. Give the structures of these products, and use mechanisms to show how they are formed.

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

(e) 1-bromohexane

Which alkyne should be used for the synthesis of each of the following ketones?

a.

b.

Which alkyne should be used for the synthesis of each of the following ketones?

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:

e.