10. Addition Reactions

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

(g)

Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to

(a) meso-2,7-dimethyloctane-4,5-diol, (CH₃)₂CHCH₂CH(OH)CH(OH)CH₂CH(CH₃)₂.

Predict the products formed when CH₃CH₂–C≡C:^–Na⁺ reacts with the following compounds.

a. ethyl bromide

b. tert-butyl bromide

c. formaldehyde

Show how you would accomplish the following synthetic conversions.

c. 1-methylcyclopentanol → 2-chloro-1-methylcyclopentanol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.

In the electrophilic addition of $H_{2}O$ to propene, what is the major organic product formed?

Which of the following represents the structure of the product formed when $C_2{H}_4$ reacts with water in the presence of an acid catalyst?

Which of the following compounds undergoes the most highly regioselective addition of $HBr$?