Liquid ethanol is chosen as the solvent for four different organic solutes at 25 °C. Structural formulas for the solutes are given below.
• Acetic acid, CH₃COOH
• Acetone, CH₃COCH₃
• 1-Hexanol, CH₃(CH₂)₅OH
• n-Hexane, CH₃(CH₂)₄CH₃
(a) Rank the four solutes from most soluble to least soluble in ethanol.
(b) Justify your ranking by comparing the types and relative strengths of intermolecular forces between each solute and ethanol molecules.
(c) Ethanol can act as both a hydrogen-bond donor and acceptor. Using structural features, explain which solute benefits most from this dual capability and which benefits least.
(d) Predict how replacing ethanol with methanol as the solvent would alter the relative solubility of 1-hexanol and acetic acid. Support your prediction with intermolecular-force arguments.