CHAPTER 9: Question 1

 

Simple Answers

starting material = S        product = R        inversion
starting material =        product = S        inversion
starting material = SS      product = SS      retention

The third case is subject to neighboring group participation in which one bromine atom first intramolecularly displaces the second to the bromonium ion intermediate shown below. The bromonium ion is an achiral meso compound which can react with thiophenolate at either carbon atom in the three membered ring to form the two enantiomers of the product.

 

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