Amino lysis of esters discussion analysis

Esters are carbonyl compounds having the general formula {\rm{RCOOR’}}RCOOR
Amino lysis is a reaction in which a chemical molecule is broken in the presence of ammonia or amines. Esters undergo an amino lysis reaction. Esters on amino lysis reaction get converted to corresponding amides. Depending on the reactant taken, different types of amides are formed. If the process of amino lysis is carried out in the presence of ammonia, primary amide is the major product. If, instead of ammonia, a primary amine is taken for conducting the amino lysis of esters, a secondary amide will be obtained. If this process is carried out in the presence of a secondary amine, a tertiary amide will be obtained. In all these cases, a molecule of alcohol is also obtained as a by-product. The reaction follows a nucleophilic addition pathway. Now, let us look at more details about the process of amino lysis and the amino lysis of esters in the presence of ammonia, primary amine, and secondary amine.

As already mentioned, amino lysis is the process that involves the breakage of an organic compound in the presence of ammonia or any amines. The word ‘amino’ means “compound having {\rm{N}}{{\rm{H}}_2}NH
group,” and ‘lysis’ means “to break”. Amino lysis can be carried out in various compounds like carboxylic acids, esters, alkyl halides, etc. If amino lysis is carried out in an alkyl halide, it replaces the halogen atom and forms a hydrogen halide. If amino lysis is carried out in carboxylic acids and esters, amides are obtained.

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The amino lysis of esters, using ammonia, yields a primary amide. This is depicted in the given figure. The reaction proceeds through a nucleophilic addition mechanism. In this reaction, ammonia is acting as a nucleophile. It attacks the carbonyl carbon. This yields an intermediate. On further proton transfer, it removes the alcoholic portion of the ester and forms the primary amide.


Amino lysis of esters can be also done using amines. Amino lysis of esters using primary amine yields a secondary amide. It is depicted in the given figure. This reaction also follows a nucleophilic addition mechanism. In this reaction, first, the nucleophilic addition of the amine to carbonyl carbon takes place. The nitrogen atom of the amine then undergoes deprotonation and loses a hydrogen atom. This results in the formation of a type of tetrahedral intermediate, which is negatively charged. For restoring the {\rm{C = O}}C=Obond in the molecules, either alkoxy \left( {{\rm{R}}{{\rm{O}}^ – }} \right)(RO
)group or the amino {\rm{RN}}{{\rm{H}}^ – }RNH
group must be lost. When the {\rm{p}}{K_a}pK
values of both the alcohols and amines are compared, amine groups are stronger bases while the alkoxy groups are weaker bases. So, the alkoxy groups are the better leaving groups; therefore the alkoxy \left( {{\rm{R}}{{\rm{O}}^ – }} \right)(RO
)group will be removed from the molecule. As a result, the {\rm{C = O}}C=Obond in the molecule will be restored, resulting in the formation of the amide.

The amylolysis of esters in presence of secondary amines yield tertiary amides. The reaction is illustrated in the figure below. The reaction mechanism of the amino lysis of esters using secondary amines is also similar to that of using the secondary amine.


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