Question

Draw the structure of two alkenes that would yield 1-methylcyclohexanol when treated with Hg(OAc)2 in water, then NaBH4:Draw the structure of two alkenes that would yield 1-methylcyclohexanol when treated with Hg(OAc)2 in water, then NaBH4:

Answer 1

Answer:

Two possible compounds are shown below- one with an exocyclic double bond and another one with an endocyclic double bond

Explanation:

Reaction of alkene with $Hg(OAc)_{2}$ gives a complex of mercurous ion.

Then water molecule attacks this complex through $S_{N}2$ type reaction at more substituted position.

$NaBH_{4}$ cleaves the resultant C-Hg bond and forms a C-H bond.

Two possible structures of an alkene is possible to yield 1-methylcyclohexanol which are shown below.