# Reaction of alpha-naphthol with benzyl iodide [duplicate]

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?