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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: Draw the products of each reaction using the two-part strategy from Sample Problem 10.7.

Question: Devise a synthesis of each compound from cyclohexene as the starting material. More than one step is needed.

a.

b.

c.

d.

Question: Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China.

(a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid.

(b) Draw the structure of a stereoisomer that has a lower melting point.

Question: What product is formed when each alkene is treated with HCl?

Question: Label each C-C double bond as E or Z. Kavain is a naturally occurring relaxant isolated from kava root.
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