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Chapter 10: Q.17. (page 402)

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.

Short Answer

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Answer

Mechanism

Step by step solution

01

Markovnikov rule

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

02

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.

03

Products of the given reactions

The addition of the hydrogen atom from HX to 3-methylcyclohexene leads to two 2°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 3° carbocation, leading to the formation of two products.

Mechanism

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Most popular questions from this chapter

Question: Which alcohols can be prepared as a single product by hydroboration–oxidation of an alkene? Which alcohols can be prepared as a single product by the acid-catalyzed addition of H2O to an alkene?

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Question: When buta-1,3-diene (CH2=CH-CH=CH2) is treated with HBr, two constitutional isomers are formed CH3CHBr-CH=CH2and Br-CH2CH=CHCH2. Draw a stepwise mechanism that accounts for the formation of both products.

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Question: Draw a stepwise mechanism for the following reaction.

Question: Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecific reaction. Draw the structure of the stereoisomers formed from each alkene.
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