VIDEO solution: Your labmate forgets to TLC their esterification reaction and decides that after 2 hours of refluxing, the reaction must be done. They concentrate the reaction mixture and take a 1H NMR. In addition to the peaks for the desired product, the spectrum includes a peak at 11.90 ppm. The student then redissolves their product mixture in DCM and washes the solution with a saturated aqueous NaHCO3 solution. They then dry the organic layer, concentrate the sample on the rotary evaporator

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