What are the products formed when phenol is reacted with $\ce{PhCH_2Br}$ (benzyl bromide)?

I can think of two ways in which the reaction would proceed. One would be the formation of an ether through SN2 mechanism. The other is formation of 4-benzylphenol (Friedel–Crafts alkylation)

Which one of the two products is likely to be formed? If both are formed, is there any preference for one being the major product?


closed as unclear what you're asking by Mithoron, Jon Custer, airhuff, Gaurang Tandon, Tyberius May 9 '18 at 15:20

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    $\begingroup$ Please specify the solvent, amount, catalyst absence or presence, temperature and then your reasoning considering all of them. If there is still a point for a question, then helping you is possible. $\endgroup$ – Güray Hatipoğlu May 7 '18 at 10:58

I believe the SN2 mechanism will predominate. The benzyl bromide is not sufficiently electrophilic to perform a Friedel-Crafts Alkylation, as that often requires the use of a metal catalyst.

  • $\begingroup$ Hey Alex, the OP didn't say we aren't permitted to use a metal catalyst. In fact, I think saying that we are performing FC alkylation assumes that we have to use the metal catalyst. So, is there any other reason why you would want to reject the EAS substitution? $\endgroup$ – Gaurang Tandon May 7 '18 at 12:35
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    $\begingroup$ Normally to do a Friedel Crafts alkylation a lewis acid or some other means of generating a carbocation is needed. I am also sure that it will be mainly SN2 as long as the system is alkaline or basic. If we were to add aluminium bromide or aluminium chloride things could get interesting as the phenol could coordinate to the aluminium. This will withdraw some electron density from the benzene ring and thus make the phenol less reactive. $\endgroup$ – Nuclear Chemist May 7 '18 at 16:00

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