In an Honors organic chemistry lab, a student devised an experiment in which she would treat benzoic acid with t-butanol in an a
cid-catalyzed esterification reaction using concentrated sulfuric acid. Regretfully, the synthetic yield of the expected ester was exceedingly low. Please explain this outcome in terms of the chemistry that actually occurred in the reaction flask. [This attempted esterification reaction would have been better suited to dicyclohexylcarbodiimide (DCC/pyridine) esterification conditions.]
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