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E2 and E1 mechanisms, Zaitsev vs Hofmann products, and substitution vs elimination competition
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Learn E2 (anti-periplanar, concerted) and E1 (carbocation intermediate) mechanisms. Understand Zaitsev's rule, Hofmann products with bulky bases, and the SN1/SN2/E1/E2 decision framework.
Predict the major alkene product when (a) 2-bromo-2,3-dimethylbutane is treated with NaOEt / EtOH, and (b) the same substrate is treated with potassium tert-butoxide / t-BuOH. Explain the difference using Zaitsev vs Hofmann selectivity.
(a) NaOEt (small base) โ Zaitsev product. E2 elimination preferentially removes the ฮฒ-H that gives the more substituted (more stable) alkene: 2,3-dimethylbut-2-ene (tetrasubstituted).
(b) KOtBu (bulky base) โ Hofmann product. The bulky base cannot easily access the more crowded internal ฮฒ-Hs, so it removes a less hindered terminal-methyl ฮฒ-H โ 2,3-dimethylbut-1-ene (the less substituted alkene). This is the textbook bulky-base = Hofmann pattern.
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