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Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain and give mechanism.

13.16     Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain and give mechanism.

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Addition of HBr to propene-
In this addition, an electrophile H^+ attacks the double bond of the alkene to form 1^0 and 2^0 carbocations-

a secondary carbocation is more stable than the primary carbocation. Thus bromide ion attacks the carbocation to form 2-bromopropane as a major product. (This mechanism is followed by Markovnikov's rule)

 

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