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Topic: why do tertiary alkyl halides prefer substitution over E1  (Read 1865 times)

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Offline frankenstein18

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why do tertiary alkyl halides prefer substitution over E1
« on: November 23, 2015, 11:42:29 PM »
why do tertiary alkyl halides prefer Sn1 over E1 even though they can undergo both?


Offline beardy

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Re: why do tertiary alkyl halides prefer substitution over E1
« Reply #1 on: November 23, 2015, 11:56:38 PM »
Tertiary alkyl halides can also undergo E2 with a strong base. Tertiary alkyl halide doesn't necessarily prefer substitution or elimination. Sometimes you get a mixture. You must consider other reagents to determine which pathway is more likely.

How to avoid mixes:

 sn1: weakly basic nucleophiles (water, alcohol)
 e1: non-nucleophilic bases: choose an acid with a weakly nucleophilic counterion [H2SO4, TsOH, or H3PO4], and heat.

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