Which among the following compounds will give a completely racemic enantiomeric pair upon heterolyti — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

For a compound to form a racemic mixture (a pair of enantiomers) during an $S_N1$ reaction, the starting material must yield a carbocation intermediate that creates a new chiral center upon nucleophilic attack. A) The product $C_6H_5-C(OH)(C_6H_5)_2$ has three identical phenyl groups and is achiral. B) The product has two identical phenyl groups and is achiral. C) $C_6H_5-CH(CH_3)-I$ contains a chiral center. When iodide leaves, it forms a planar, resonance-stabilized benzylic carbocation. Attack by $H_2O$ from either the top or bottom face is equally probable, yielding equal amounts of d- and l- 1-phenylethanol (a racemic mixture). D) The product has two identical methyl groups and is achiral.