Question

What is the solubility of benzoic acid in 100 mL of dichloromethane at 25 degrees Celsius? It is the only value I can't find for lab.

Answer 1

Benzene forms dimer by forming hydrogen bonds between carbonyl group of one molecule and hydroxyl group of other molecule ,so its polarity is reduced.Thus ,it is soluble in low polarity solvents like dichloromethane.

solubility in g/100g of solvent values of benzoic acid as found in chemical database-

carbon tetrachloride (CCl4) (25 deg C) 4.36

chloroform(CCl3) (25 deg C) 17.84

Value not available for DCM (CH2Cl2),needs to be determined experimentally.

As DCM (dipole moment 1.6D )is mor polar than chloroform (dipole moment 1.04D),so benzoic acid must be less soluble in DCM than Chloroform,having even lower solubility.