The mechanism for the given reaction that accounts for the observed stereochemistry is to be explained. Concept introduction: The electrophilic addition of R O − B r molecule across the C=C bond can take place similar to the addition of H O − B r . In the first step, the electron-rich C=C bond attacks the bromine atom and the lone pair of the same bromine atom attacks the other carbon of C=C bond forming cyclic bromonium ion intermediate and simultaneously breaks the O − Br bond. The bromonium ion is a three-membered ring with one positively charged bromine atom. The alkoxide ion produced in the first step acts as a nucleophile, and the positively charged bromine of bromonium ion intermediate is the leaving group. Thus, the reactions proceed through S N 2 where the nucleophilic alkoxide ion attacks one of the carbon of the three-membered intermediate of bromonium ion from the opposite side of positively charged bromine atom resulting in the breaking of one C − Br bond. As the nucleophile approaches from the opposite side of the positively charged bromine atom, the stereochemistry of groups B r and O R is trans.

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Chapter 12, Problem 12.39P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction that accounts for the observed stereochemistry is to be explained.

Concept introduction:

The electrophilic addition of RO−Br molecule across the C=C bond can take place similar to the addition of HO−Br. In the first step, the electron-rich C=C bond attacks the bromine atom and the lone pair of the same bromine atom attacks the other carbon of C=C bond forming cyclic bromonium ion intermediate and simultaneously breaks the O−Br bond. The bromonium ion is a three-membered ring with one positively charged bromine atom. The alkoxide ion produced in the first step acts as a nucleophile, and the positively charged bromine of bromonium ion intermediate is the leaving group. Thus, the reactions proceed through SN2 where the nucleophilic alkoxide ion attacks one of the carbon of the three-membered intermediate of bromonium ion from the opposite side of positively charged bromine atom resulting in the breaking of one C−Br bond. As the nucleophile approaches from the opposite side of the positively charged bromine atom, the stereochemistry of groups Br and OR is trans.

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