Oxymercuration -demurcuration reaction of 1-methyl cyclohexene gives

Options

A. cis-2-Methyl cyclohexene gives
B. trans-2-Methyl cyclohexanol
C. 1-Methyl cyclohexanol
D. Mixture of cis and trans-2-methyl cyclohexanol.

Explanation

To solve the problem of the oxymercuration-demercuration reaction of 1-methylcyclohexene, we can follow these steps:

### Step 1: Understand the Reaction Mechanism
The oxymercuration-demercuration reaction involves two main steps:
1. Oxymercuration: The alkene reacts with mercuric acetate (Hg(OAc)₂) in the presence of water to form a mercurial alcohol intermediate.
2. Demercuration: The mercurial intermediate is then treated with sodium borohydride (NaBH4) to remove the mercury and form the final alcohol product.

**Hint:** Remember that oxymercuration follows Markovnikov's rule, where the more substituted carbon atom gets the -OH group.

### Step 2: Identify the Starting Material
We start with 1-methylcyclohexene, which is a cyclic alkene with a methyl group attached to one of the carbon atoms in the ring.

**Hint:** Visualize the structure of 1-methylcyclohexene to understand where the double bond and the methyl group are located.

### Step 3: Perform Oxymercuration
In the oxymercuration step, mercuric acetate reacts with 1-methylcyclohexene. The double bond of the alkene attacks the mercury, leading to the formation of a cyclic mercurinium ion. Water then attacks the more substituted carbon of the mercurinium ion, resulting in the formation of a mercurial alcohol intermediate.

**Hint:** Focus on the regioselectivity of the attack by water, which will lead to the formation of the more stable carbocation.

### Step 4: Perform Demercuration
In the demercuration step, the mercurial alcohol intermediate is treated with sodium borohydride (NaBH4). This step replaces the mercury with a hydrogen atom, yielding the final alcohol product.

**Hint:** Remember that the demercuration step is crucial for removing the mercury and forming the final alcohol.

### Step 5: Identify the Final Product
After completing the oxymercuration-demercuration reaction, the product formed is 1-methylcyclohexanol. This is the alcohol where the hydroxyl (-OH) group is added to the more substituted carbon of the original alkene.

**Hint:** Check the structure of 1-methylcyclohexanol to confirm that the -OH group is correctly positioned.

### Final Answer
The oxymercuration-demercuration reaction of 1-methylcyclohexene gives **1-methylcyclohexanol**.