An
inquiry-based learning approach was implemented into comprehensive
organic chemistry experiments focusing on the formation process of N-phenylbenzamide from the reaction between N-benzylideneaniline and benzoyl peroxide in commercial dimethyl sulfoxide.
Students conducted comparative experiments using alternative reagents
or reaction conditions to produce products. After structure determination
of the products by NMR and GC–MS, the observed structural difference
can lead to the conclusion that the CN double bond cleavage
from N-benzylideneaniline releases aniline, which
then reacts with benzoyl peroxide to form the product N-phenylbenzamide. This comprehensive experiment provides a heuristic
inquiry-based training for upper-division chemistry undergraduate
students to gain experimental skills, analyze data, interpret spectra,
and elucidate the amide formation process.