The possible alkenes to produce 1-methylcyclohexanol are and . (Refer to the attached image)
Further explanation:
Oxymercuration-demercuration reaction:
Oxymercuration-demercuration converts alkene into alcohol in two steps. In the initial step, the alkene is reacted with salt and nucleophile such as alcohol and water to produce an organomercury intermediate. In second step, the carbon-Hg bond in organomercury intermediate is converted into C-H bond.
In this method the product is obtained in accordance with Markovnikov’s rule, and rearrangement of carbocation does not take place.
The mechanism of Oxymercuration-demercuration is as follows(Refer to the attached image):
Step 1: break and form mercuroacetic cation and ions.
Step 2: The mercuroacetic cation reacts with a double bond and forms a cyclic cation.
Step 3:The cyclic intermediate is attacked by the nucleophile to the most substituted side according to Markovnikov’s rule and forms organomercury intermediate.
Step 4: the carbon-Hg bond in organomercury intermediate is converted into C-H bond.
The methylcyclohexanol has alcohol on tertiary carbon thus the double bond must be attached to the tertiary carbon in initial alkene. This means there are only two possible alkenes that can have double bond attached to the tertiary carbon. These alkenes are 1-methylcyclohexene and methylenecyclohexane.
Learn more:
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Answer details:
Grade: Senior School
Subject: Chemistry
Chapter:Oxymercuration-demercuration reactions
Keywords: Oxymercuration-demercuration reaction, alkenes, structure of two alkenes, yield 1-methylcyclohexanol, Hg(OAc)2, NaBH4.