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.

Show how you might use olefin metathesis to assemble the following alkenes from smaller units:

(a)

(b)

Starting with ethyne, describe how the following compounds can be synthesized:

a. (3S,4R)-4-bromo-3-hexanol and (3R,4S)-4-bromo-3-hexanol

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

(g)

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.

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(h)

Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.

(a)