Synthesis of Ethers and Epoxides

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From alkyl halides and alcohols

Mechanism!; S_N2 reaction, Williamson synthesis
Note that some alkene is also formed, by competition from the E2 reaction; more substituted halides will undergo only the E2 elimination.
McMurry 8.3, 11.5, 11.9, Fessenden 5.3A, 5.10, 8.2B, Schmid 13.8C, 12.2 - 12.5, 12.14

From alkenes

+ CH₃OH

This method is better than the Williamson synthesis if the carbon is not primary.
McMurry 18.4, Fessenden 10.8, Schmid 8.10, 13.8

Epoxides

These strained ethers are very easy to make (from alkenes) but very reactive.

Stereospecific!
McMurry 17.4, 18.7, Fessenden 10.13, Schmid 13.10, 8.6

Mechanism! Stereospecific!
McMurry 18.7, Fessenden 8.3, Schmid 13.10, 8.9

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Last update Feb. 1, 1999