Give the structures of the products you would expect when each alcohol reacts with (1) HCl, ZnCl₂; (2) HBr; (3) PBr₃; (4) P/I₂; and (5) SOCl₂.
(a) butan-1-ol
(b) 2-methylbutan-2-ol

Starting with (R)-1-deuterio-1-propanol, how could you prepare

b. (S)-1-deuterio-1-methoxypropane?

Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.

(a) 1-methoxybutane

(b) 2-ethoxy-2-methylpropane

(c) benzyl cyclopentyl ether

Show how you would convert hex-1-ene to each of the following compounds. You may use any additional reagents and solvents you need.

(a) 2-methoxyhexane

(b) 1-methoxyhexane

(c) 1-methoxyhexan-2-ol

Show how you would convert (S)-hexan-2-ol to

(a) (S)-2-chlorohexane.

(b) (R)-2-bromohexane.

(c) (R)-hexan-2-ol.

In each case, show how you would synthesize the chloride, bromide, and iodide from the corresponding alcohol.

(a) 1-halobutane (halo = chloro, bromo, iodo)

(b) halocyclopentane

A graduate student attempted the following reaction and did not isolate the expected product.

(a) What product did they isolate?

(b) What reagent should they have used instead to get their desired product?

Suggest the appropriate reagents to carry out the following transformations.

(f)

Suggest a reagent for the transformation of a 1° alcohol to a 1° alkyl halide.