In a 100 mL round bottom flask equipped for magnetic stirring, place 0.54 g of 4-chlorobenzhydrol (for preparation see preceding experiment), 5 mL of ethyl acetate, 0.1 g of tetrabutylammonium hydrogen sulfate, and 10 mL of bleach (approx. 8% NaOCI). The flask may be loosely stoppered to prevent splashing. Stir the mixture vigorously and continuously at room temperature.
After 60 min, transfer the mixture to a separatory funnel (you may use a little additional ethyl acetate to complete the transfer), remove the aqueous layer, and wash the ethyl acetate solution with 5 mL of 5% aqueous $NaHCO_3$ and then with 5 mL of saturated aqueous NaCl. Dry the organic solution over $K_2CO_3$, then transfer the liquid to a 50 mL round bottom flask and remove the solvent by simple distillation using a steam bath as a heat source to prevent charring of the product. When the solvent has been removed, allow the flask to cool, break up the resulting solid, and allow it to dry until the next lab period. During the next lab period, determine the yield, obtain the infrared spectrum, and record the melting point (the reported melting point of 4-chlorobenzophenone is 75-77 $^\circ$C). Perform a 2,4-dinitrophenylhydrazine test
