During the workup portion of the reaction of alkenes with HBr as described in the experiment provided, a student transferred the
reaction mixture to a separatory funnel, rinsed the reaction flask with diethyl ether, and added the ether rinses to the separatory funnel. The student then added sodium bicarbonate to the separatory funnel. Extremely vigorous bubbling occurred. What did the student do wrong
Because of the acid-base reaction, as sodium bicarbonate is introduced to the separatory funnel, the additional or unreacted HBr reacts vigorously to yield CO2 gas, which exits the separatory funnel together with any dissolved compound(s) in the ether layer. This is due to a wrong and incorrect selection of the solvent mixture and the addition of sodium bicarbonate to an acidic solution.
Nothing to do with it until it has leaked out of the separatory funnel. Even then, the student may separate the components from the remaining reaction mixture by washing the ether coating layer several times with brine water, then running it into a dry sodium sulfate bed and evaporating solvent ether under decreased pressure.
