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Organic Chemistry
Found in: Page 402

Short Answer

Question: Treatment of 3-methylcyclohexene with HCl yields two products, 1-chloro-3-methylcyclohexane and 1-chloro-1-methylcyclohexane. Draw a mechanism to explain this result.



See the step by step solution

Step by Step Solution

Step 1: Markovnikov rule

The carbon atom with a higher number of hydrogen atoms in the bond gets the hydrogen atom from HX bonded to it.

Step 2: Carbocation stability

The more substituted and stable carbocation is favored to form the major product. However, the products also contain some amount of that product that has resulted from a less substituted carbocation.

Step 3: Products of the given reactions

The addition of the hydrogen atom from HX to 3-methylcyclohexene leads to two carbocations. In one case, the carbocationic center is next to the carbon having a methyl group.

Hence, the carbocation undergoes a 1,2-H shift to form a carbocation, leading to the formation of two products.


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