[google1]

Hey everyone,

For education purposes-- trying to understand what the product(s) would be for benzyl bromide + methanol? 

My current understanding of reactions are E1, E2, Sn1, Sn2, Dehydration...  I am don't see how this reaction would involve E1 or E2 since there are no beta hydrogens.  I only see substitution (Sn2?) reaction because the oxygen in methanol can attack the carbon adjacent to bromine.  The bromine could fall off during this as well.  Then the OH- would lose its hydrogen to satisfy its positive charge.  Stereochemistry would not be a concern since there are no chiral carbons.  This would produce a benzyl ether? 

Am I headed in the right direction?  Something seems funny in this hypothesis...  Help will be appreciated!

[google1]

Actually, it is Sn1 reaction isn't it.  Even though the bromine is attached to a primary carbon the carbocation is resonance stabilized and the bromide is stabilized.  The methanol nucleophile is a weak nucleophile so no Sn2 reaction will occur. 

This is probably still wrong but if anyone can lend me some good ol' knowledge that would be great!

[saden99]

I'm still thinking about this, but I don't think there is a reaction. Keep in mind that benzene is rather stable on its own and a substituent might only effect where more addition occurs on the benzene ring (Ortho, para, meta).


HOWEVER....look up Grignard reagents and have fun

[macman104]

You are correct that it cannot undergo E1 or E2, and the primary carbon encourages SN2.  However, check your answer, you have lost an atom in the process of drawing your answer.