Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.
d. trans-hex-2-ene
e. 1,1-dibromohexane
f. 2,2-dibromohexane

When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

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

a. hex-1-yne

b. hex-2-yne

c. cis-hex-2-ene

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

(d) cyclohexanone

(e) CH₃CH₂CH₂CHO

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

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?