(a)
Interpretation:
The mechanism and the structure of the product of the nucleophilic addition-elimination reaction between pyridine and an acid chloride are to be drawn.
Concept introduction:
Pyridine is a moderately strong nucleophile as the lone pair of the nitrogen atom is not involved in resonance (and
(b)
Interpretation:
Why the reaction involving pyridine does not interfere with the production of the desired amide product of the given reaction is to be explained.
Concept introduction:
Pyridine is a moderately strong nucleophile as the lone pair of the nitrogen atom is not involved in resonance (and aromaticity). When it is used as a solvent in a nucleophilic addition-elimination reaction, it can compete with the reagent, adding to the carbonyl carbon of the substrate. The product of the reaction has a positive charge on the nitrogen of the pyridine group and, therefore, is reactive toward nucleophilic addition-substitution reaction.
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