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What is the mechanism of the reaction between 2-methylpropene and hydrobromic acid in the presence of peroxide? What are the intermediates formed during the reaction and how do they contribute to the overall reaction mechanism?

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The reaction between 2-methylpropene  also known as isobutene  and hydrobromic acid  HBr  in the presence of peroxide follows a free radical mechanism, specifically, the anti-Markovnikov addition of HBr to the alkene. This reaction is also known as the peroxide effect or the Kharasch effect. The overall reaction can be represented as:2-methylpropene + HBr  1-bromo-2-methylpropaneThe mechanism involves the following steps:1. Initiation: The peroxide  usually a weak O-O bond  undergoes homolytic cleavage by heat or light, generating two alkoxy radicals  RO .R-O-O-R  2 RO2. Propagation Step 1: The alkoxy radical reacts with HBr, abstracting a hydrogen atom and forming a bromine radical  Br  and an alcohol  ROH .RO + HBr  ROH + Br3. Propagation Step 2: The bromine radical reacts with 2-methylpropene, forming a secondary free radical at the less substituted carbon  anti-Markovnikov  due to the greater stability of the secondary radical compared to the primary radical.Br + CH2=C CH3 2  CH3C CH3 24. Propagation Step 3: The secondary radical reacts with another molecule of HBr, abstracting a hydrogen atom and forming the final product, 1-bromo-2-methylpropane.CH3C CH3 2 + HBr  CH3CBr CH3 25. Termination: Two free radicals combine to form a stable molecule, ending the chain reaction. This can occur in various combinations, such as two bromine radicals, two alkoxy radicals, or a bromine radical and an alkoxy radical.Br + Br  Br2RO + RO  R-O-O-RBr + RO  R-O-BrThe intermediates formed during the reaction are the alkoxy radicals, bromine radicals, and the secondary carbon radical. These intermediates contribute to the overall reaction mechanism by propagating the chain reaction and leading to the formation of the final product, 1-bromo-2-methylpropane.
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