An unknown molecular compound X has the empirical formula C₃H₆O. The compound is tested for solubility at room temperature in three solvents of comparable polarity index:
• Water – complete miscibility
• Ethanol – complete miscibility
• n-Hexane – negligible solubility (two layers form)
Assume X does not ionize in any solvent.
(a) Based solely on the solubility data, identify the dominant type(s) of intermolecular force acting between molecules of X and water. Explain your reasoning.
(b) Two structural isomers that match the empirical formula are shown below in condensed form:
I. CH₃–CH₂–CHO (propanal)
II. CH₃–CO–CH₃ (propanone, commonly called acetone)
Using intermolecular-force arguments, determine which structure more plausibly corresponds to compound X. Support your choice with at least two pieces of evidence derived from the solubility observations.
(a) Based solely on the solubility data, identify the dominant type(s) of intermolecular force acting between molecules of X and water. Explain your reasoning.
(b) Two structural isomers that match the empirical formula are shown below in condensed form:
I. CH₃–CH₂–CHO (propanal)
II. CH₃–CO–CH₃ (propanone, commonly called acetone)
Using intermolecular-force arguments, determine which structure more plausibly corresponds to compound X. Support your choice with at least two pieces of evidence derived from the solubility observations.
(c) Sketch or describe a particulate-level diagram that depicts one molecule of your chosen structure interacting with two water molecules. Indicate the orientation of the water molecules and label any hydrogen bonds or dipole–dipole interactions.