Is caffeine more soluble in water or in dichloromethane? How can you tell?

After checking in several different places, and discussing with my peer tutor, I would have to go with the peer tutor's information: more soluble in methylene chloride than water.

"Of course, molecules generally can be assigned to both classes, partially. And thus, caffeine is a polar molecule, which has a significant hydrophobic portion (look at the structure). In water, caffeine dissolves chiefly via formation of hydrogen bonds involving atoms with free electron pairs (N

and O). In Ch2Cl2, these interactions give way to generalized hydrophobic interactions of the nonpolar dichloromethane with hydrophobic parts of the molecule, such as -CH3 etc.

Likewise, caffeine readily dissolves in chloroform and several other organic solvents.

Solubility of caffeine in water is about 9 times less than in

dichlorometane - thus when a solution of caffeine in water is brought in contact with dichloromethane, most of the caffeine will migrate into the organic layer. "

Caffeine is more soluble in dichloromethane. It has to do with the polarity of these items. Dicholormethane has more similar properties to caffeine than water does and therefore it is more soluble. By the way caffeine is polar and so is dichloromethane. Good luck!

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Is caffeine more soluble in water or in dichloromethane? How can you tell?