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Chapter 10: Q.18. (page 402)

Question: Addition of HBr to which of the following alkenes will lead to a rearrangement?

Short Answer

Expert verified

Answer

The addition of HBr leads to rearrangement in alkene c.

Step by step solution

01

Rearrangement of carbocations

The carbocation undergoes 1,2-H shift to become more stable, thus forming the major product of the reaction.

02

Carbocation stability

The more substituted carbocation is more stable. Due to the electron-donating tendency of the alkyl group, the carbocation centers achieve stability to some extent.

03

Products of the given reactions

The addition of HX to alkenes enables carbocation formation by the addition of the hydrogen atom of HX to the less substituted carbon atom in the C=C bond.

Carbocations undergo a 1,2-H shift to achieve stability.


a.

Addition of H+leads to the formation of a 3°carbocation, which is a very stable intermediate. Hence, it does not undergo rearrangement.


b.

Formation of 2°carbocations takes place and both of which are not able to form a more stable 3°carbocation upon rearrangement. Hence, no rearrangement takes place.


Carbocation in b

c.

One of the 2°carbocation undergoes rearrangement to form a more stable 3°carbocation.

Carbocation in c

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Most popular questions from this chapter

Question: What three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?

Question: Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.

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