OOOEther Syntheses 1example:OO:–example:1. Devise efficient syntheses for each of the following types of ether.Primary—PrimaryO:–example:Choose either SN2 route (typical Williamson synthesis):BrPrimary—SecondaryO:–example:Secondary—Secondary: tough! Either way gives a strong probability of elimination! Show SN2 and SN1BrUse the secondary alkoxide as the nucleophile, and a primary halide in an SN2 process:Tertiary—anythingOHUse a tertiary alcohol or an alkene, a trace of acid, and lots of the other alcohol, in an SN1-type route:+HO++HOlikely to give E2with acid,likely to give some E1OH++HO+with acid,use large excess ofthe primary alcohol+HOwith acid, use large excessof the alcohol.(Can you showmechanism?)with acid, use large excessof the alcohol.(Can you showmechanism?)CH3IWeek 380
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