Question: Identify the reagents (a–h) needed to carry out each reaction.

Alkyl halides can be converted to alkyl bromide using the reagent ${\mathbf{PBr}}_{\mathbf{3}}$. The bromocyclohexane hence formed, can be reduced using a strong base such as tert-butyloxide. The reaction is shown below:

Conversion of cyclohexanol to bromocyclohexane and reduction

The hydroxyl group of cyclohexanol can also be converted to a tosylate group and reduced in the same manner as shown below:

Tosylation and reduction

The hydroxyl group is reduced using a strong acid, converted to bromo cyclohexene using NBS, and reduced using a strong base.

Reduction of alcohol and further reactions

The halohydrination of cyclohexene is done using HOCl, which is further converted to an epoxide via reduction and then to a diol using a hydroxyl ion source.

Halohydrination, epoxidation, and formation of diol