Using hex-1-ene 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.)
a. 1,2-dibromohexane
b. hex-1-yne
c. 2,2-dibromohexane

What is the major product obtained from the reaction of each of the following compounds with excess HCl?

c. CH₃CH₂C☰CCH₂CH₂CH₃

Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.

a. HBr (1 mol)

b. HBr (2 mol)

Predict the major product(s) of the following reactions:

c. cyclooctyne + 2 HBr

d. *hex-2-yne + 2 HCl

Show how hex-1-yne might be converted to

f. 2,2-dibromohexane.

Predict the products of reaction of pent-1-yne with the following reagents.

a. 1 equivalent of HCl

b. 2 equivalents of HCl

c. excess H₂, Ni

Which of the following best represents the major organic product formed when a terminal alkyne reacts with one equivalent of $H_{\mathrm{Cl}}$ under standard conditions?

Predict the major product(s) of the following reactions:

a. phenylacetylene + 2 HBr

b. hex-1-yne + 2 HCl