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Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the...

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Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the...

Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols.
1. BHs / THF 2. HO, OH Major Product Mechanism The borane and hydrogen add to the alkene in a concerted reaction step. This m
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.
1. BHs / THF 2. HO, OH Major Product Mechanism The borane and hydrogen add to the alkene in a concerted reaction step. This means that the borane and the hydrogen add syn to the alkene. The borane arranges itself on the least hindered (less substituted) side of the double bond. This leads to the formation of Anti-Markovnikov Alcohols. During the course of the reaction each borane is actually alkylated 3 times. The trialkylate borane for the above reaction is shown below. Trialkylated Borane Catalytie Hydrogenation - adds hydrogen across alkenes. Effectively reduces alkenes into alkanes. a Hz. Pd/c or PtO2 Ether or Acetic Acid solvent Ether or acelic Acid Major Product The catalyst adds the hydrogen in a syn addition. Also the catalyst usually tends to add the hydrogens to the least hindered face of the alkene. Oxidation of Alkenes

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t-methyl Mator product cyclopentene flowever, at higher temperature, product gets delapkailed again and leads the the formati


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