For the experiment, \"Cannizzaro Reaction: the Conversion of p-Nitrobenzaldehyde
ID: 1038794 • Letter: F
Question
For the experiment, "Cannizzaro Reaction: the Conversion of p-Nitrobenzaldehyde into p-Nitrobenzoic Acid and p-Nitrobenzyl Alcohol," note 1 in part 1 of the procedure warns against the use of acetone to rinse glassware. Why should acetone be avoided?
Part 1 of the Procedure:
"Place 0.300g of p-nitrobenzaldehyde into a clean, dry 10-mL E. flask or 5-mL conical vial. [Note 1]...Use glass stirring rod to grind the p-nitrobenzaldehyde into a powder. USing a Pastuer pipet, add 3 mL of 30% KOH down the walls of the vessel, flushing down any p-nitrobenzaldehyde that adheres to the walls. Add a magnetic stir bar or spine vane. Turn on the magnetic stirrer and stir for 15-20 min. Label two 15-mL centrifuge tubes 'acid' and 'alcohol,' respectively. Transfer the reaction mixture to the tube labeled 'acid.' Add 2 mL of distilled or deionized water and 2 mL of dicholomethane to the centrifuge tube. Attach a lid and shake the tube to mix the layers. Vent the tube periodically...."
Explanation / Answer
Although acetone don't have an alpha-H, but it can undergo a Cannizzaro-type reaction after a nucleophilic attack on alpha-H, transferring one of their two carbon groups rather than the hydride that would be present on an aldehyde.
Thus the reaction would be interfered and consequently % yield and purity of the product is compromised