Leaving Group Conversions Summary Practice Problems

Complete the following multistep synthesis in two steps. (Note: use a tosyl ester formation as one of the steps.)

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

Provide the final products of each of the reactions given below. 

a. Cyclopentylmethanol + TsCl/pyridine 

b. product of (a) +LiAlH4

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.