Ethers can be prepared by Williamson synthesis which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether can't be prepared by this method. Explain.

Ethers can be prepared by Williamson synthesis which an alkyl halide i

1.	Ethers can be prepared by Williamson synthesis which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether can't be prepared by this method. Explain.
Answer» Solution :In order to prepare di-tert butyl ETHER, sodium tert-butoxide must be reacted with tert-butyl bromide. Alkoxides are not only NUCLEOPHILES but they are STRONG base as well. They react with `3^(@)` alkyl halides leading to the elimination reaction. When tert-butyl-bromide reacts with sodium tert-butoxide instead of SUBSTITUTION, elimination takes place. As a result of this elimination reaction, Iso BUTYLENE is formed instead of di-tert butyl ether. `{:(""CH_(2)-H""CH_(3)""CH_(2)""CH_(3)),("\|""\|""\|\|""\|"),(H_(3)C-C-Br+Na-O-C-CH_(3) overset("Elimination")rarr H_(3)C-C-CH_(3)+H_(3)C-C-OH+NaBr),("\|""\|" "Iso-butylene" "\|"),(""CH_(3)""CH_(3)""CH_(3)),("Tert-butyl bromideSodium.tert butoxide2-methylpropan-2-ol"):}` `{:(""CH_(2)-H""CH_(3)),("\|""\|"),(H_(3)C-C-Br+Na-O-C-CH_(3) overset("Substitution")rarr "No reaction"),("\|""\|"),(""CH_(3)""CH_(3)),("Tert-butyl bromideSodium.tert butoxide"):}`