1. For solutes that are dissolved because of intermolecular attractions with the solvent, state the intermolecular attractions involved.
There are dipole-dipole attractions and hydrogen bonding between polar acetone and polar water.
There are dipole-dipole attractions and hydrogen bonding between ethanol and water. There are also dipole-dipole attractions between ethanol and diethyl ether.
There are hydrogen bonding, dipole-induced dipole forces, and dipole-dipole forces between sucrose and water.
2. For solutes that are dissolved because of reaction with the solvent, write the balanced equation involved.
C6H5OH + NaOH
C6H5ONa + H2O
C6H5CHO + H2SO4
m-benzaldehyde sulfonic acid
C6H5CH2OH + H2SO4 C6H5CH2OH2+ + HSO4-
C6H5COOH + NaOH C6H5COONa + H2O
C6H5COOH + NaHCO3 C6H5COONa + CO2 + H2O
C6H5NH2 + HCl → C6H5N+H3Cl-
3. On the basis of solubility behaviour, determine the best solvent to differentiate the following pairs of compounds. a. CH3COOH (acetic acid) and CH3(CH2)5COOH
The best solvent to use to differentiate acetic acid from heptanoic acid would be sodium bicarbonate (NaHCO3) as the stronger the acid, the more soluble it is in sodium bicarbonate.
b. CH3CH2OCH2CH3 and CH3CH2OH
The best solvent to use to differentiate diethyl ether from ethanol is water. Diethyl ether is only slightly soluble in water unlike ethanol which is completely soluble. c. toluene and benzaldehyde
The best solvent to use to differentiate toluene from benzaldehyde is concentrated sulfuric acid (H2SO4) since benzaldehyde is soluble in sulfuric acid unlike toluene. d. tert-butyl chloride and tert-butanol
The best solvent to use to differentiate tert-butyl chloride and tert-butanol is water since tert-butanol is very soluble in water while tert-butyl chloride is not.
Jain, M. (Ed.). (2008, June). Aromatic Conversions. Competition Science Vision, 474.
McMurry, J. (2011). Alcohols, Phenols, Ethers and Their Sulfur Analogs. Fundamentals of Organic Chemistry, 7th Edition (pp. 256-283). Belmont, CA: Brooks/Cole.
Solomons, G., Fryhle, C., & Snyder, S. (2014). Organic Chemistry, 11th Edition. USA: John Wiley & Sons, Inc.