Stanislao Cannizzaro was an Italian chemist. He made his first contribution to chemical research in 1851 when he, along with F. S. Cloez, a French chemist, prepared cyanimide using ammonia and cyanogen chloride in an ethereal solution. Later that year, he became a professor in physical chemistry in Alessandria. It is there where Cannizzaro discovered that aromatic aldehydes can be decomposed into a mixture of the corresponding acid and alcohol by using an alcoholic solution of potassium hydroxide. This is now known as the Cannizzaro Reaction.
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Next week, add 10 mL water and try to dissolve all the solid material in the flask 5. Pour aqueous solution into a separatory funnel and extract with two 5 mL portions of dichloromethane 6. Combine the dichloromethane extracts and set aside 7. If the 125 mL flask still contains any solids, transfer the aqueous layer back to the flask, add 5 mL of water and try to dissolve the remaining solids 8. Extract the aqueous layer twice more with 5 mL portions of dichloromethane 9. Combine all dichloromethane solutions and extract with 5 mL water 10. Combine the water layers and set aside, labeling the flask ‘acid’ 11.
Add 1. 2 g anhydrous sodium sulfate to the dichloromethane solution which should contain your 4-nitrobenzyl alcohol product 12. Stopper the flask, label it ‘alcohol’, swirl the flask occasionally, and let the trace amount of water be absorbed by the anhydrous sodium sulfate. 13. While the 4-nitrobenzyl alcohol / dichloromethane solution is drying, prepare an ice bath using a 250-mL beaker 14. Place the aqueous flask labeled ‘acid’ in the ice bath and slowly add 9 mL of 6M HCl 15. Does a precipitate form? What is its color? 16. Collect the 4-nitrobenzoic acid product by vacuum filtration rinsing the flask with water.
Transfer the solid to a water glass and let air dry overnight. 18. After drying weigh the crude product, determine its melting point and calculate the percentage yield. 19. Carefully decant or filter the ‘dried’ dichloromethane solution labeled ‘alcohol’ to a clean, labeled, evaporating dish and place in the vent hood. 20. Let the dichloromethane evaporate from the dish overnight 21. Collect the dry crude 4-nitrobenzyl alcohol, determine its mass and melting point, and calculate the percentage yield. a. Based on your melting point determination, indicate whether your products are pure or need to be recrystallized. . What solvent will you use to purify each product should purification by recrystallization is necessary?
