Some charged
nucleophiles are actually poor
bases. ... So if you see a
nucleophile like NaCl, NaBr, KCN, and so on, it will favor SN2 over E2. In contrast, the bulky
base below (tert-butoxide ion)
is a strong base but a poor
nucleophile due to its great steric hindrance, so an E2 reaction is much more likely than SN2.Nov 30, 2012
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