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Addition of HBr to propene yields 2-bromopropane, while inpresence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain and give mechanism. |
Answer» SOLUTION :Addition of HBr to propene is an ionic electrophilic addition REACTION in which the electrophile, i.e., `H^+` first ADDS to give a more stable `2^@` carbocation. In the 2nd second, the carbocation is rapidly attacked by the nucleophile `Br^-` ION to give 2-bromopropane In presence of benzoyl peroxide , the reaction is still electrophilic but the electrophile here is a `oversetdot(Br)` free radical which is obtained by the action of benzoyl peroxide on HBr In the first step, `oversetdot(Br)` radical adds to propene in such a way as to generate a more stable `2^@` radical . In the second step, the free radical thus obtained rapidly abstracts a hydrogen atom from HBr to give 1-bromopropane. it is evident that although both reactions (i.e., in presence or absence of benzoyl peroxide ) are electrophilic addition but it is due to different order or sequence of addition of H and Br atoms which gives different PRODUCTS. |
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