12. Alcohols, Ethers, Epoxides and Thiols

When SOCl₂ is used in place of HCl, only one product results. Why are these conditions better?

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