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Synthesis Of Ethers: Williamson Ether Synthesis And Alcoxymercuration

Ethers are compounds with the formula R-O-R. An ether can be easily recognized by spotting an oxygen in between two carbons. Let's go over the major ways to synthesize ethers. There are two major ways to make ethers which are Williamson Ether Synthesis And Alcoxymercuration.


Williamson ether synthesis is a reaction that converts alcohols into ethers (C-O-C). In the first step, alcohol is deprotonated using a strong base such as NaH. The alkoxide ion that is created is a strong nucleophile and can attack primary alkyl halides and tosylates in an SN2 reaction. The O- attacks the carbon the leaving group is attached to and the leaving group leaves.

Note: If the alkyl halide or tosylate is not primary, E2 will happen instead of SN2.

Williamson Ether Synthesis
Williamson Ether Synthesis

How to predict the reactants of Williamson Ether Synthesis when product is given
How to predict the reactants of Williamson Ether Synthesis when product is given


In this reaction, the starting material, alkene, reactions with 1.Hg(OAc)2, ROH 2.NaBH4 to produce an ether.

Product: Turn double bond into single and add OR to the most substituted carbon from the double bond. The other carbon gets the hydrogen. No Rearrangements!

alcoxymercuration predict the product
alcoxymercuration predict the product

Error: the picture above says "add OH" and should say "add OR" instead

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