Preparation of Alcohols

 

➡️Preparation of Alcohols

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• Preparation of Alcohols
  1. From alkenes
     • By acid catalysed hydration:
       1. Alkenes react with water in the presence of acid as catalyst to form alcohols.
       2. In case of unsymmetrical alkenes, the addition reaction takes place in accordance with Markovnikov’s rule (Unit 13, Class XI).
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     • By hydroboration–oxidation:
       1. Diborane (BH3)2 reacts with alkenes to give trialkyl boranes as addition product. This is oxidised to alcohol by hydrogen peroxide in the presence of aqueous sodium hydroxide. The
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       3. The addition of borane to the double bond takes place in such a manner that the boron atom gets attached to the sp2 carbon carrying greater number of hydrogen atoms. The alcohol so formed looks as if it has been formed by the addition of water to the alkene in a way opposite to the Markovnikov’s rule. In this reaction, alcohol is obtained in excellent yield.
  2. From carbonyl compounds
     • (i) By reduction of aldehydes and ketones:
       1. Aldehydes and ketones are reduced to the corresponding alcohols by addition of hydrogen in the presence of catalysts (catalytic hydrogenation).
       2. The usual catalyst is a finely divided metal such as platinum, palladium or nickel. It is also prepared by treating aldehydes and ketones with sodium borohydride (NaBH4) or lithium aluminium hydride (LiAlH4)
       3. Aldehydes yield primary alcohols whereas ketones give secondary alcohols.
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     • By reduction of carboxylic acids and esters:
       1. Carboxylic acids are reduced to primary alcohols in excellent yields by lithium aluminium hydride, a strong reducing agent.
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       3. However, LiAlH4 is an expensive reagent, and therefore, used for preparing special chemicals only.
       4. Commercially, acids are reduced to alcohols by converting them to the esters (Section 11.4.4), followed by their reduction using hydrogen in the presence of catalyst (catalytic hydrogenation).
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  3. From Grignard reagents
     1. Alcohols are produced by the reaction of Grignard reagents (Unit 10, Class XII) with aldehydes and ketones.
     2. The first step of the reaction is the nucleophilic addition of Grignard reagent to the carbonyl group to form an adduct. Hydrolysis of the adduct yields an alcohol.
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     4. You will notice that the reaction produces a primary alcohol with methanal, a secondary alcohol with other aldehydes and tertiary alcohol with ketones.