Question

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

Draw the structure of two alkenes that would yield 1-methylcyclohexanol when treated with Hg(OAc)2 in water, then NaBH4. I have done the first, but need help with the second

Draw the structure of two alkenes that would yield


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Concepts and reason

This problem is based on the concept of oxymercuration-demercuration reaction of alkenes.

Oxymercuration is an oxidation reaction which on further reduction gives an alcohol, this reaction is called oxymercuration-reduction reaction or oxymercuration-demercuration reaction.

Fundamentals

Alkenes have high electron density due to the presence of pi-bond due to which they are highly reactive towards the chemical species which are electron deficient in nature. Therefore, alkenes undergo oxymercuration-demercuration reaction on treatment with Hg(OAc)2{\rm{Hg}}{\left( {{\rm{OAc}}} \right)_2} and followed by the reduction with NaBH4{\rm{NaB}}{{\rm{H}}_4} in order to give an alcohol.

The structure of the product is shown below:

First alkene which can form this product is shown as follows:

Hg(OAc)༡
འདམ་ ་
C
ལ་བཤ་འམ་ འཐད།
Hg-OAC
NaBH,
ཨ་
H20

Second alkene which can form this product is shown as follows:

_Hg-OAC
OH
Hg(OAc)2
ОН
NaBH,
H2O

Ans:

The structure of two alkenes are as follows:

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