Three structural isomers of C₄H₁₀O are tested for their solubility in liquid water at 20 °C. The isomers are illustrated below.
• n-Butan-1-ol, CH₃CH₂CH₂CH₂OH
• sec-Butan-2-ol, CH₃CH₂CH(OH)CH₃
• tert-Butan-2-ol, (CH₃)₃COH
(a) Predict the order of solubility of the three isomers in water, from highest to lowest.
(b) Provide a detailed explanation that considers both hydrogen-bond formation and the impact of molecular branching on dispersion forces and steric hindrance.
(c) A particulate diagram shows several water molecules arranged around one molecule of tert-butan-2-ol. Describe two specific deviations you would expect this diagram to exhibit compared with an analogous diagram for n-butan-1-ol, and relate each deviation to intermolecular interactions.
(d) Design an experimental procedure (at the qualitative level) that could verify your predicted order of solubility without using advanced instrumentation. Include the observations that would confirm the ranking.