Discussion
The major product of the following reaction is :
Answer: A
The major product is Ph-CH(OMe)-CH2-OH, 2-methoxy-2-phenylethanol.
Under acidic conditions the epoxide oxygen is protonated, and the C-O bond to the benzylic carbon weakens because the developing positive charge there is stabilised by the phenyl ring. Methanol therefore attacks the more substituted, benzylic carbon in an SN1-like opening, and the oxygen stays on the CH2 as a primary OH.
Ph-CH(OH)-CH2-OMe is the product of basic conditions (methoxide attacks the less hindered CH2). The diol would need water as the nucleophile, and styrene would require deoxygenation, not ring opening.
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