What major product results when 2-bromo-2-methylbutane is treated with sodium ethoxide?

| May 27, 2018

You have a classic set up for an E2 elimination.
You are using a good nucleophile – good base, one of four darn good bases OH, OR, NH2, and R-
The substrate or alkyl halide is classic for E2, tertiary. So you get elimination E2 not Sn2. Sn2 could occur with NaOCH3 but only if primary RX or CH3X.
You get 2-methylbut-2-ene.
If you still want the substitution product, when you can’t go Sn2, go Sn1, use a weak nucleophile – weak base, or HOCH3. If you can’t do it strong, do it weak… you always get a mix of Sn1/E1 but if you don’t add heat, you get mostly Sn1.

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