1.) 1-bromo-2-cyclohexylethane -----------> vinylcyclohexane
Dehydrohalogenation using bulky base in DMSO solvent . Using NaOEt in EtOH as solvent will
give substitution product rather than elimination one.
2.) vinylcyclohexane ---------------> 1-cyclohexylethane-1,2-diol
Hydroxylation using following reagents
(i) Cold aqueous alkaline KMnO
4 OR
(ii) OsO
4 followed by hydrolysis