Final answer:
Industrial synthesis of amides typically avoids using acyl chlorides due to their high reactivity. Amides are less electrophilic and more stable because of nitrogen's ability to donate electron density through resonance. Amidation, the preferred industrial process, involves combining a carboxylic acid with an amine and eliminating a water molecule.
Step-by-step explanation:
Industrial Synthesis of Amides
The industrial synthesis of amides typically avoids the use of acyl chlorides due to their high reactivity. Acyl chlorides are very reactive with nucleophiles because of the highly nucleophilic carbonyl carbon they contain. In contrast, amides are much less electrophilic, as evidenced by electrostatic potential maps showing that the carbonyl carbon is less positive, making them more stable. This reduced reactivity is a result of nitrogen in the amide being less electronegative than oxygen, and its ability to donate electron density to the carbonyl carbon via resonance, reducing its positive charge.
Furthermore, the synthesis of amides usually involves a reaction between a carboxylic acid and an amine or ammonia, which is a process called amidation. During this reaction, a molecule of water is eliminated to form the amide linkage. This contrasts with the use of acyl chlorides, which due to their high reactivity, are not typically found in biological systems and are less suitable for the mild conditions preferred in industrial processes.
Lastly, amides themselves are known for their resistance to hydrolysis, requiring catalysis by acids, bases, or enzymes in biological systems to break down. The production of amides by reaction of a carboxylic acid with an amine is a fundamental reaction in organic chemistry, with direct relevance to the synthesis of many biologically active molecules, including proteins.