Question

Write increasing order of solubility in water : phenol, catechol, resorcinol and quinol

Answer 1

Answer: Quinol> resorcinol>Phenol>catechol

Explanation:

Catechol has very low solubility in water because it forms intramolecular hydrogen bonding. Remaining can form intermolecular hydrogen bonding with water.so these easily and has high solubility in water

Answer 2

The increasing order of water solubility for the given compounds is  Quinol<Phenol<REsorcinol<Catechol.

• Quinol or hydroquinone is the least soluble in the water among given compounds as it has keto-enol tautomerism. Due to this, the polar hydroxy groups get converted to keto, which has decreased hydrogen bonding capability with water molecules.
• Phenol has only one polar hydroxyl group whereas catechol and resorcinol have two hydroxy groups. So phenol is less soluble than catechol and resorcinol.
• Resorcinol has two hydroxyl groups that are in meta position on the benzene ring whereas, in catechol, the hydroxyl groups are ortho to each other.
• In resorcinol, there is intermolecular hydrogen bonding between two resorcinol molecules. So hydrogen bonding with water is less.
• In catechol, the hydroxyl groups are close to each other and there is intermolecular hydrogen bonding. So no hydrogen bonding between catechol molecules occurs and solubility in water increases.