Organic 2 Review Problem 266

Organic 2 Review Problem 266 - 250 PRACTICAL O RGANIC...

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250 PRACTICAL ORGANIC CHEMISTRY •ulphonylation is complete, the reaction product can then be steam-distilled without transference to another vessel. Required: Aniline, 4 ml.; monomethylaniline, 4 ml.; dimethyl- aniline, 4ml.; toluenc- p -sulphonyl chloride, 16 g. Prepare a mixture containing 4 ml. of each of the above three amines. Place the mixture in the conical flask, add 60 ml. of 10 % sodium hydroxide solution, and also 60 ml. of water to moderate the subsequent reaction. Add 16 g. of finely powdered toluene- p -sulphonyl chloride, cork the flask securely and shake the contents vigorously for 20-30 minutes: the mixture becomes warm, and a fine emulsion of the unchanged dimethylaniline and the molten sulphonyl-methylaniline forms in the alkaline solution. Finally the temperature falls towards the end of the above period of shaking. Now replace the cork by the steam-distillation fitting, and steam-distil the reaction mixture until fine drops of dimethylaniline can no longer be detected in the distillate leaving
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