When SOCl₂ replaces HCl in the reaction, it only produces one product. Explain why.

In each case, show how alcohol can be converted into the given halides (chloride, bromide, and iodide).
a. 1-halopropane (halo = chloro, bromo, iodo)
b. halocyclohexane

Predict the expected products when the following two alcohols are treated with each of the given reagents.
Reagents: (1) HCl, ZnCl₂; (2) HBr; (3) PBr₃; (4) P/I₂; and (5) SOCl₂.
Alcohols: a. propan-1-ol ; b. 2-methylpropan-2-ol

Show the reaction to convert (S)-pentan-2-ol into the following products.

a. (S)-2-chloropentane

b. (R)-2-bromopentane

c. (R)-pentan-2-ol

Consider the following reaction:

Is the product shown the correct expected product from the reaction? If not, draw the correct product and provide the proper reagent that must be used.

Draw the major products formed from the reaction of cis-3-ethylcycloheptanol with the reagents below. Include stereochemistry, if applicable.

(i) concentrated HBr

(ii) TsCl/pyridine, then NaBr