The “normal” and “abnormal” products formed in the reaction of allyl bromide with hydrogen bromide under a variety of conditions are to be identified. Out of these two products, the product that is the result of addition in accordance with Markovnikov's rule and the one which corresponds to addition opposite to the Markovnikov's rule is to be given. Concept introduction: Addition of hydrogen halides to alkenes produces alkyl halides. This addition may be electrophilic, which proceeds through the formation of carbocation intermediates. During electrophilic addition, a proton is added to the double bond such that the more stable carbocation is produced. The overall addition is according to the Markovnikov rule. The hydrogen atoms get added to the carbon atom, which has more hydrogens attached to it. The addition of hydrogen halides to alkenes may be through the formation of free radicals as intermediates. During free radical addition, the bromine is added to the double bond such that a more stable alkyl free radical is produced. The overall addition takes place with a regioselectivity opposite to that of Markovnikov rule: The hydrogen atoms get added to the carbon atom which has less hydrogens attached to it.

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Chapter 10.5, Problem 10P

Interpretation Introduction

Interpretation:

The “normal” and “abnormal” products formed in the reaction of allyl bromide with hydrogen bromide under a variety of conditions are to be identified. Out of these two products, the product that is the result of addition in accordance with Markovnikov's rule and the one which corresponds to addition opposite to the Markovnikov's rule is to be given.

Concept introduction:

Addition of hydrogen halides to alkenes produces alkyl halides.

This addition may be electrophilic, which proceeds through the formation of carbocation intermediates.

During electrophilic addition, a proton is added to the double bond such that the more stable carbocation is produced.

The overall addition is according to the Markovnikov rule. The hydrogen atoms get added to the carbon atom, which has more hydrogens attached to it.

The addition of hydrogen halides to alkenes may be through the formation of free radicals as intermediates.

During free radical addition, the bromine is added to the double bond such that a more stable alkyl free radical is produced.

The overall addition takes place with a regioselectivity opposite to that of Markovnikov rule: The hydrogen atoms get added to the carbon atom which has less hydrogens attached to it.

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