10. Addition Reactions

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

(g) <IMAGE>

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 <IMAGE> 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. <IMAGE>

h. <IMAGE>

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

a. <IMAGE>

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

c. <IMAGE>

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

a. <IMAGE>

b. <IMAGE>

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