12. Alcohols, Ethers, Epoxides and Thiols

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?

What stereoisomers do the following reactions form?

c.

d.

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

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