Because the 1°carbocation RCH2+ rearranges and a 2-alkene is formed. Even if a 1-alkenes forms it tends to rearrange in acid to a 2-alkene.
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Friday, February 7, 2020
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 ?
Because dehydration of alcohol is accompanied by a hydride shift leading to an intermediate 3°carbocation which gives 2, 3-dimethylbut-2-ene.
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Why dehydration proceeds in acid but not in base?
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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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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