Experiment # 4

Oxidation and reduction of

benzaldehyde:
 Cannizzaro reaction:
In a 50 mL beaker introduce benzaldehyde (7.5 g) and a saturated solution of sodium
hydroxyde (4.5 g of pellets in the minimum amount of water). Heat the mixture by means of
a bain-marie for 30 min while stirring vigorously. Next, cool the beaker down and the
minimum amount of cold water to dissolve the solid. Then, transfer the mixture into a
separating flask, extract with dichloromethane (2x20 mL) and collect the organic layers in a
100 mL beaker The content of the beaker is mixed vigorously with a solution of sodium
bisulfate (5 mL) in order to remove the unreacted benzaldehyde. If a precipitate is formed,
filter through a Buchner funnel. and wash it with dichloromethane (10 mL); finally dry it and
weigh it out. The organic layer is washed consecutively with a dilute solution of sodium
hydroxide (5 mL) and water until a neutral pH is reached. The resulting organic layer is dried
over anhydrous sodium sulfate (~1g) and evaporated by means of a rotary evaporator. Weigh
the mass of product (benzyl alcohol) obtained. The remaining aqueous phase is cooled down
in an ice bath and treated with concentrated HCl until pH = 1.
The resulting solid is filtered through a Büchner funnel, washed twice with cold water and
finally dried over filter paper.

Recrystallization:
Dissolve the solid completely in hot water (30 mL) and let the solution cool
down slowly until benzoic acid crystallizes in the form of white needles. The
solid is isolated by filtration and dried over filter paper. Weigh the mass of
product (benzoic acid) obtained.