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An optically active secondary alcohol of structure CH3-CH(OH)-C6H5 (1-phenylethanol) is treated with sodium metal to give alkoxide (A). Compound A then reacts with CH3I via an SN2 reaction to give product (B). Identify product (B).
- CH3-C(C6H5)(H)-OCH3 (geminal methyl phenyl ether, incorrect framework)
- CH3-CH(OCH3)-C6H5
- C6H5-CH(OCH3)-CH3
- CH3O-CH(C6H5)-CH3
Correct answer: CH3-CH(OCH3)-C6H5
Solution
CH3-CH(OH)-C6H5 + Na -> CH3-CH(O^-Na⁺)-C6H5 (A). A + CH3I (SN2 at primary carbon) -> CH3-CH(OCH3)-C6H5 (B) + NaI. This is Williamson ether synthesis.
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