Question

Explain why the reaction of (+)-3 bromo -3-methyl hexane with aqueous NaOH gives a racemic mixture of the product rather than (+)- or (-)-3-methyl-3-hexanol?​

Answer 1

This is because the carbon to which the leaving group is attached is stereogenic ( atom to which different groups are bound such that its mirror image is non-superimposable ) . Here only three groups are attached to positively charged carbon atom hence it is sp² hyberdized.Neucleophile will attack on either side of carbon to give racemic mixture.