Ether synthesis?

[marmar]

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so I am a little confused here! In the Kaplan book, it says that for ether to form we need alkoxide to attack a alkyl halide in SN2 reaction to form ether and the only case where we can use alcohol instead of alkoxy for ether synthesis is in case of phenol and with use of NaOH. In the destroyer maps, it also says we can not directly get ether from reaction of alcohol with alkyl halide but we can do so by adding NaH to the alcohol first which I assume converts the alcohol. ok now the topscore has a question where alcohol attacks an alkyl halide with no other reagent to get ether. so if on the exam they ask for the reaction product and they do not give you any other reagent, would you choose and ether or you would say no reaction?😕

 

[funktion]

I think it would depend on the kind of alcohol in the rxn. The kaplan book provides the case of phenols reacting with NaOH because the phenol forms a stable phenoxide due to aromaticity which could then react with alkyl halide to form ether. Other alcohols such as propanol or butanol might form alkoxides but not likely as alkoxides are highly unstable.

 

[klutzy1987]

so I am a little confused here! In the Kaplan book, it says that for ether to form we need alkoxide to attack a alkyl halide in SN2 reaction to form ether and the only case where we can use alcohol instead of alkoxy for ether synthesis is in case of phenol and with use of NaOH. In the destroyer maps, it also says we can not directly get ether from reaction of alcohol with alkyl halide but we can do so by adding NaH to the alcohol first which I assume converts the alcohol. ok now the topscore has a question where alcohol attacks an alkyl halide with no other reagent to get ether. so if on the exam they ask for the reaction product and they do not give you any other reagent, would you choose and ether or you would say no reaction?😕

An alcohol is not a base and therfore wouldnt react to form a ether. First add the NaH which is a strong base to abstratct a proton and the it works. Ifthe reaction doesnt have it just assume that it did and they forgot to write it.