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In preparation for Olympiad, I faced this question:

$\alpha$ naphthoxide ion (analogue to phenoxide ion) is reacted with benzyl iodide in two different mediums:

$(i)$ DMSO (dimethyl sulfoxide)

$(ii)$ $\ce{CF3CH2OH}$

Write the major products obtained in the above two cases.

DMSO is essentially polar aprotic solvent, whereas (I think) $\ce{CF3CH2OH}$ is polar protic solvent. Thus, I think in latter, $\ce{O-}$ will be involved in hydrogen bonding, thus major product should be p-benzyl naphthol whereas in DMSO ether would be formed.

But, these aren't probably the correct answers. Where did I go wrong? And what are the correct answers?

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