acid catalyzed hydrolysis of amide mechanism


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  • The most general way for obtaining amides involves the activation of the carboxylic function by means the conversion of carboxylic acids into the corresponding acid chlorides [5,6,7,8].
    Subsequently this reactive derivative is coupled with the appropriate amine to yield the corresponding amide.

  • What is the purpose of the acid catalyst in the hydrolysis of an amide?

    The acid acts as a catalyst for the reaction between the amide and water.
    The alkaline hydrolysis of amides actually involves reaction with hydroxide ions, but the result is similar enough that it is still classed as hydrolysis.

  • What is the mechanism of acid catalysed hydrolysis?

    The nucleophile involved in acid-catalyzed hydrolysis of the ester is H2O.
    The water molecule attacks the carbonyl carbon atom by donating the oxygen's lone pair of electrons and forming a bond.
    It is a nucleophilic substitution reaction as water act as a nucleophile, by attacking the carbonyl carbon of ester.

  • What is the mechanism of acid hydrolysis of amides?

    Hydrolysis of Amide
    In an acidic medium, amide interacts with the water molecule to give a carboxylic acid and the salt of ammonia or amine salt.
    In a basic medium, amide interacts with the water molecule to give a carboxylic acid and the salt of ammonia or amine salt.

  • The first step in acid-catalyzed amide hydrolysis is the protonation of the carbonyl oxygen atom of the amide group. The rate-determining step is the nucleophilic attack of a water molecule to the carbon atom of the amide group. During this process one proton is transferred to the water phase.
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