HYDROLYSIS AMIDE

Amide is a compound that is not reactive, since the protein consists of amino aminoyang linked by amide bonds. Amide does not react with halide ions, ionkarboksilat, alcohol, or water because in each case, the incoming nucleophile is basalemah of the amide group to go

Amide can react with water and alcohol if the reaction mixture is heated under acidic

Molecular orbital theory can explain why the amide is not reactive. Amide resonance memilikikontributor important where one partner shares with karbonkarbonil nitrogen, which contains a lone pair orbital overlap of the empty orbitals of guguskarbonil

Lower energy state overlap-one partner is not a base or nucleophilic, and raises the energy of the orbital of the carbonyl group, making it less reactive toward nucleophiles. Amide NH₂  group can be dehydrated to a nitrile. Dehydrating reagents commonly used for this purpose is P₂O₅, POCl₃, SOCl₃

Hydrolysis of amides with acid catalyst

When the amide is hydrolyzed in acidic conditions, acid proton of the carbonyl oxygen, increase the susceptibility of the carbonyl carbon to nucleophilic attack. Nukleofilikoleh attack of water on the carbonyl carbon causes the tetrahedral intermediate compound I, which beradadalam equilibrium with form rather than protons, tetrahedral intermediates II.Reprotonasi can occur either at the tetrahedral intermediates of oxygen to reform I ataupada nitrogen to form a tetrahedral intermediate III. Protonation at the nitrogen preferred because the NH₂ is a stronger base than the OH.Dari two possible groups went on a tetrahedral intermediate III group (-OH danNH₃), NH₃ is a weak base, so it is released, forming a carboxylic acid end sebagaiproduk. Because the reaction is carried out in acid solution, NH₃ be protonated setelahdiusir of tetrahedral intermediates. This prevents the reverse reaction

Why can not hydrolyze amide without a catalyst? In the reaction without catalyst, amidatidak protonated. Therefore, the water, a very poor nucleophile, should be neutral menyerangamida far more susceptible to nucleophilic than serangandari amidaterprotonasi. In addition, the group of the tetrahedral intermediate is not protonated in the reaction without a catalyst. Therefore, the-OH group is away from the tetrahedral intermediate-because-OH is a weak base of the-NH₂ amide reform. A amidabereaksi with alcohol under acidic conditions for the same reason will bereaksidengan water under acidic