Predict whether each compound has a greater solubility in water or hexane. Hexane Water Answer Bank HO HO propionaldehyde (iodomethyl)cyclopentane OH HO piperidine vitamin C Indicate the kinds of intermolecular forces that occur between vitamin C and the solvent that it has greater solubility in. HO HO HO OH London dispersion ion-dipole dipole-dipole hydrogen bonding Indicate the kinds of intermolecular forces that occur between piperidine and the solvent that it has greater solubility in. hydrogen bonding London dispersion ion-dipole dipole-dipole Indicate the kinds of intermolecular forces that occur between propionaldehyde and the solvent that it has greater solubility in. H London dispersion hydrogen bonding dipole-dipole ion-dipole Indicate the kinds of intermolecular forces that occur between (iodomethyl)cyclopentane and the solvent that it has greater solubility in. dipole-dipole hydrogen bonding London dispersion ion-dipole
The Correct Answer and Explanation is :
Solubility Prediction
To determine the solubility of the compounds in water or hexane, we need to look at their polarity and the types of intermolecular forces they exhibit.
- Propionaldehyde: This compound has a polar carbonyl group (C=O), making it polar overall. It is more likely to be soluble in water because water is also polar and can form hydrogen bonds with the carbonyl group.
- Solubility: Water
- Intermolecular Forces: Dipole-Dipole, Hydrogen Bonding (since the carbonyl group can participate in hydrogen bonding with water molecules).
- (Iodomethyl)cyclopentane: This compound has a nonpolar cyclopentane ring and a polar iodomethyl group (–CH2I), which makes it a polar molecule but with a significant nonpolar character due to the cyclopentane ring. Since it has some polarity due to the iodine atom (which is electronegative), it will likely have better solubility in water than in hexane.
- Solubility: Water
- Intermolecular Forces: Dipole-Dipole, London Dispersion (the iodine atom can induce dipole interactions, but London dispersion forces also play a role).
- Piperidine: This compound contains a nitrogen atom in a six-membered ring that can participate in hydrogen bonding. The nitrogen is relatively electronegative, so the molecule is polar and will likely dissolve in water because of its ability to form hydrogen bonds with water molecules.
- Solubility: Water
- Intermolecular Forces: Hydrogen Bonding, London Dispersion.
- Vitamin C: Vitamin C is a highly polar molecule with multiple hydroxyl groups (–OH), which can form hydrogen bonds with water molecules. These interactions make it highly soluble in water.
- Solubility: Water
- Intermolecular Forces: Hydrogen Bonding.
Summary Table
| Compound | Solubility in Water | Solubility in Hexane | Intermolecular Forces in Water |
|---|---|---|---|
| Propionaldehyde | Water | Hexane | Dipole-Dipole, Hydrogen Bonding |
| (Iodomethyl)cyclopentane | Water | Hexane | Dipole-Dipole, London Dispersion |
| Piperidine | Water | Hexane | Hydrogen Bonding, London Dispersion |
| Vitamin C | Water | Hexane | Hydrogen Bonding |
Explanation
- Water is polar and forms hydrogen bonds, so compounds that are polar or capable of hydrogen bonding tend to dissolve in it.
- Hexane is nonpolar and interacts mainly through London dispersion forces. Nonpolar compounds are more soluble in hexane due to similar types of intermolecular forces.
- The solubility of each compound depends on its polarity and its ability to form hydrogen bonds, dipole-dipole interactions, or London dispersion forces. More polar compounds with hydrogen bonding capabilities (like Vitamin C) will be soluble in water, while nonpolar compounds will dissolve better in hexane.
Now, I will generate an image representing the molecular structure of these compounds showing their polarity to help visualize the solubility trends.
Here is the visual representation of the molecular structures of propionaldehyde, iodomethylcyclopentane, piperidine, and vitamin C, along with indications of their polarity and solubility trends in water versus hexane. The image highlights the key functional groups in each compound and their interactions with the solvents. Let me know if you’d like further clarification or adjustments!