Both of these effects are illustrated below. The carboxylate ion would be rapidly protonated by hydronium ion. Chymotrypsin, one of the digestive enzymes secreted by the pancreas, belongs to a family of enzymes that cleave proteins into smaller peptides. List two reasons why the amide hydrolysis is slow in the absence of chymotrypsin. An amide is a poor electrophile due to excellent resonance between the carbonyl carbon and the amide nitrogen.
Water is a poor nucleophile due to low polarizability and high electronegativity of oxygen.
The hydrogen bond with the carbonyl oxygen serves to remove electron density from this oxygen. Thus, the hydrogen bond increases the electrophilicity of the carbonyl carbon, assisting attack by weakly nucleophilic water. Imidazole is aromatic. Briefly explain your answer to the previous question. Both nitrogen atoms would be sp 2 hybridized.