Problem: For each of the following pairs of solute and solvent, predict whether the solute would be soluble or insoluble. After making your predictions, you can check your answers by looking up the compounds in The Merck Index or the CRC Handbook of Chemistry and Physics. Generally, The Merck Index is the easier reference book to use. If the substance has a solubility greater than 40 mg/mL, you may conclude that it is soluble. a) Malic acid in waterb) Naphthalene in waterc) Amphetamine in ethyl alcohold) Aspirin in watere) Succinic acid in hexane ( Note: the polarity of hexane is similar to that of petroleum ether.)f) Ibuprofen in diethyl etherg) 1-Decanol (n-decyl alcohol) in water

FREE Expert Solution

Solubility: depends on intermolecular forces between solvent and solute


a) Malic acid in water

malic acid: polar → can form hydrogen bonds

water: polar → can form hydrogen bonds


Malic acid is soluble in water.

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Problem Details

For each of the following pairs of solute and solvent, predict whether the solute would be soluble or insoluble. After making your predictions, you can check your answers by looking up the compounds in The Merck Index or the CRC Handbook of Chemistry and Physics. Generally, The Merck Index is the easier reference book to use. If the substance has a solubility greater than 40 mg/mL, you may conclude that it is soluble. 


a) Malic acid in water

b) Naphthalene in water

c) Amphetamine in ethyl alcohol


d) Aspirin in water

e) Succinic acid in hexane ( Note: the polarity of hexane is similar to that of petroleum ether.)

f) Ibuprofen in diethyl ether

g) 1-Decanol (n-decyl alcohol) in water

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