Class 11 Chemistry - Chapter Hydrocarbons NCERT Solutions | Addition of HBr to propene yields 2-brom
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.
Addition of HBr to propene is an example of an electrophilic substitution reaction.
Hydrogen bromide provides an electrophile H+. This electrophile attacks the double bond to form 1° and 2° carbocations.
Secondary carbocations are more stable. Hence, the former predominates since it will form at faster rate. Thus, in the next step, Br- attacks the carbocation to form 2 - bromopropane as major product.
This reaction follows Markovnikov's rule where the negative part of the addendum is attached to the carbon atom having a lesser number of hydrogen atoms.
In the presence of benzoyl peroxide, an addition reaction takes place anti to Markovnikov's rule. The reaction follows a free radical chain mechanism as:
Secondary free radicals are more stable than primary radicals. Hence, the former predominates since it forms at a faster rate. Thus, 1 - bromopropane is obtained as the major product.
In the presence of peroxide, Br free radical acts as an electrophile. Hence, two different products are obtained on addition of HBr to propene in the absence and presence of peroxide.
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2 Comment(s) on this Question
Why the HCl,HF and HI don't show peroxide effect
Why the HCl,HF and HI don't show peroxide effect
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