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

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

Step-by-step 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.