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

Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.

(a) PBr₃

(b) SOCl₂ 

(c) Lucas reagent

Suggest how you would convert trans-4-methylcyclohexanol to

a. trans-1-chloro-4-methylcyclohexane.

b. cis-1-chloro-4-methylcyclohexane.

What stereoisomers do the following reactions form?

a.

b.

What stereoisomers do the following reactions form?

c.

d.

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.