Show how you would synthesize the following compound. As starting materials, you may use any alcohols containing five or fewer carbon atoms and any necessary solvents and inorganic reagents.

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

(g)

Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(a)

Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how the following syntheses could be carried out:

a.

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

(h)

When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, synthesize the following aldehydes beginning with an organic molecule containing three carbons or fewer.

(b)

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(a)

a. Propose a mechanism for the following reaction.

2 (CH₃)₂C=CH–CH₃ + cat. H⁺ → 2,3,4,4-tetramethylhex-2-ene

b. Show the first three steps (as far as the tetramer) in the BF₃–catalyzed polymerization of propylene to form polypropylene.

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)