The Williamson reaction often competes with the base-catalyzed elimination of the alkylating agent, and the nature of the leaving group as well as the reaction conditions (particularly the temperature and solvent) can have a strong effect on which is favored. In particular, some structures of alkylating agent can be particularly prone to elimination.
When the nucleophile is an aroxide ion, the Williamson reaction can also compete with alkylation on the ring since the aroxide is an ambident nucleophile.
Read more about this topic: Williamson Ether Synthesis
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