Portmess Homework Q&S 76

Portmess Homework Q&S 76 - 70 ALCOHOLS AND ALKYL...

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4.14 1-Butanol is a primary alcohol; 2-butanol is a secondary alcohol. A carbocation intermediate is possible in the reaction of 2-butanol with hydrogen bromide but not in the corresponding reaction of 1-butanol. The mechanism of the reaction of 1-butanol with hydrogen bromide proceeds by displacement of water by bromide ion from the protonated form of the alcohol (the alkyloxonium ion). Protonation of the alcohol: Displacement of water by bromide: The slow step, displacement of water by bromide from the oxonium ion, is bimolecular. The reaction of 1-butanol with hydrogen bromide follows the S N 2 mechanism. The reaction of 2-butanol with hydrogen bromide involves a carbocation intermediate. Protonation of the alcohol: Dissociation of the oxonium ion: Capture of sec -butyl cation by bromide: The slow step, dissociation of the oxonium ion, is unimolecular. The reaction of 2-butanol with
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