Why caffeine soluble in chloroform?

Answer 1

Caffeine is a polar molecule thus it has hydrophobic portions, and dichloromethane is s polar organic solvent which is fairly good at dissolving most organic molecules. In water caffeine dissolves for the most part via formation of hydrogen bonds where atoms with free electron pairs are involved, and the solubility of caffeine in water in 2.2mg/mL at 25 C, 180 mg/mL at 80 C, and 670 mg/mL at 100 C. where caffeine is not all soluble in water at room temperatureWhen caffeine is brought in close contact with dichloromethane most of the caffeine migrates into the organic layer.