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Mobile App Chapter 10: Q.18. (page 402)
Question: Addition of HBr to which of the following alkenes will lead to a rearrangement?
Short Answer
Answer
The addition of HBr leads to rearrangement in alkene c.
Step by step solution
Rearrangement of carbocations
The carbocation undergoes 1,2-H shift to become more stable, thus forming the major product of the reaction.
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.
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 leads to the formation of a carbocation, which is a very stable intermediate. Hence, it does not undergo rearrangement.
b.
Formation of carbocations takes place and both of which are not able to form a more stable carbocation upon rearrangement. Hence, no rearrangement takes place.
Carbocation in b
c.
One of the carbocation undergoes rearrangement to form a more stable carbocation.
Carbocation in c
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