Determine which compound is more soluble in water for each of the following pairs: (i): cyclohexane or tetrahydro-2H-pyran and (ii): tetrahydrofuran or 1,3-dioxolane. Explain.
A. (i): Tetrahydro-2H-pyran is more soluble than cyclohexane because it can form stronger intermolecular interactions (hydrogen bonding) with water molecules; (ii): 1,3-dioxolane is more soluble than tetrahydrofuran because it can form more hydrogen bonding per molecule with water than tetrahydrofuran.
B. (i): Tetrahydro-2H-pyran is more soluble than cyclohexane because it can form covalent bonds with water molecules; (ii): 1,3-dioxolane is more soluble than tetrahydrofuran because it can form more covalent bonds per molecule with water than tetrahydrofuran.
C. (i): Cyclohexane is more soluble than tetrahydro-2H-pyran because water and cyclohexane are both non-polar molecules; (ii): Tetrahydrofuran is more soluble than 1,3-dioxolane because it can form more hydrophobic interactions with water molecules.
D. (i): Cyclohexane is more soluble than tetrahydro-2H-pyran because it can form covalent bonds with water molecules; (ii): Tetrahydrofuran is more soluble than 1,3-dioxolane because it can form more covalent bonds per molecule with water.
