[neobenzene]

Hi...I've been recently taught that in the Williamson ether synthesis, the halide to be reacted, should be a primary halide. This is because if the halide is secondary or tertiary, due to greater sterric crowding, elimination dominates over substitution, and an alkene is formed.

Now, what if the halide I'm using is benzyl chloride....benzene ring with a -CH₂Cl attached to it. I'm  not sure how to draw it using the SMILES engine.

Anyways, my question is, if we use benzyl chloride, and any sodium alkoxide (RONa), what will the product be? Will it be an ether, since the halide is primary, or will it be an alkene, since the halide has a bulky benzene ring?

Thanks!

[discodermolide]

Benzyl chloride cannot form an alkene. So you will form the ether.

[neobenzene]

Why can't it form an alkene?

[discodermolide]

Because there is no proton to initiate the elimination.
You cannot break the aromaticity.
You will not get

or

or


The first molecule does not make any sense.

[neobenzene]

Thanks!!