Which of the following syntheses will best produce the following target molecule?

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.

(c)

Propose a synthesis:

Propose a synthesis:

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(f)

Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.

(d)

Show how the following compounds can be prepared, using ethyne as one of the starting materials:

2. 1-phenyl-2-butyn-1-ol

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

g. pentanal, CH₃CH₂CH₂CH₂CHO

h. pentan-2-one, CH₃–CO–CH₂CH₂CH₃

i. (±) 3,4-dibromohexane