[juand.ro97]

Hi, I'd like to know if this mechanism I proposed for the dehydration of 2-naphtol with methanol to form ether  for my laboratory report is correct. Also, why is it that formation of ether by this method is only viable for symmetrical ethers, I assume it's because you would obtain a mix of product because instead of methanol it could be another molecule of 2-naphtol that reacts.

[orgopete]

You may not know the relative basic its of the oxygen atoms directly, but you might assume that the more acidic methanol or naphthol are, the less basic the oxygen. What might this suggest. Optionally, look up requirements for SN2 reactions.

[Alwin Kristen]

Sorry but that reaction mechanism cannot be right. Nuclophilic substitution should happen from opposite direction of leaving group. Aromatic naphthol is planar structure which means that methanol have to attack from INSIDE of the ring. That's obviously impossible. Also Sn1 is impossible because of positive charge is localized to sp2 hybridized orbital outside the ringsystem.