OH- is a very poor leaving group (a strong base) hence it cannot be eliminated under basic conditions. But in the presence of acid -OH is converted to -OH2 a very good leaving group and thus elimination occurs.
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Friday, February 7, 2020
Why alcohols do not undergo base induced dehydration in the same way that alkyl halides are dehydrohalogenated ?
In the dehydration reaction of alcohols the leaving group is -OH- which is a very strong base. Thus reaction cannot proceed in the presence of other base.
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To synthesize 2, 3-dimethylbut-1-ene in the better yield dehydrohalogenation of 2, 3-dimethyl-1-bromobutane is preferred over dehydration of 2, 3-dimethylhutan-1-ol. Why ?
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