Question

Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by the addition of water. Demercuration of the product with NaBH4 yields a Markovnikov Alcohol. 1. Hg(OAc)2, H2O 2. NaBHE Major Product Mechanism The addition of Hg* leads to the formation of a mereurinium ion intermediate which resembles the bromonium ion intermediate which is formed during halogenation of alkenes. The nucleophilic water attacks the mercurinium ion intermediate on the more substituted side leading to the formation of Markovnikov Aleohols. Hydroboration - involves the addition of borane to the alkene in a concerted step. Treatment of the alkylated borane yields an Anti-Markovnikov Alcohol.

Answer 1

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