Which among the following compounds will give a completely racemic enantiomeric pair upon heterolytic cleavage and subsequent nucleophilic attack by via an mechanism?

Question

Which among the following compounds will give a completely racemic enantiomeric pair upon heterolytic cleavage and subsequent nucleophilic attack by $H_2O$ via an $S_N1$ mechanism?

Prashant Kotian · Accepted Answer

Correct answer: C. For a compound to form a racemic mixture (a pair of enantiomers) during an reaction, the starting material must yield a carbocation intermediate that creates a new chiral center upon nucleophilic attack. A) The product has three identical phenyl groups and is achiral. B) The product has two identical phenyl groups and is achiral. C) contains a chiral center. When iodide leaves, it forms a planar, resonance-stabilized benzylic carbocation. Attack by 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.

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