Draw the structure of the product (s) formed on mixing propanoic acid and aniline and then the new organic product formed on heating. Be sure to show formal charges where necessary.

Structure of the product has been shown below

Explanation:

N atom in aniline acts as a nucleophile and carbonyl group of propanoic acid acts as an electrophilic center. A nucleophilic acyl substitution reaction occurs on mixing and heating mixture of aniline and propanoic acid. In this reaction an amide is formed. Reaction mechanism goes through addition-ellimination pathway at carbonyl center. Full reaction mechanism has been shown below.