Question

Phenol dissolves easily in-
A) Dilute $HCl$
B) Both $NaOH$ and $HCl$
C) $NaOH$ solution
D) Sodium bicarbonate solution

Answer 1

Hint: We must have to remember that the dilute Hydrochloric acid is a strong acid while sodium hydroxide is a base. Sodium bicarbonate or sodium hydrogen carbonate, chemical compound\[NaHC{O_3}\], a white crystalline or granular powder, commonly known as bicarbonate of soda or baking soda. It is soluble in water and very slightly soluble in alcohol.

Complete answer:
We also need to know that the phenols are similar to alcohols but form stronger hydrogen bonds. Thus, they are more soluble in water than alcohol and have higher boiling points. Phenols occur either as colorless liquids or white solids at room temperature and may be highly toxic and caustic. Similar to alcohols, phenols have hydroxyl groups that can participate in intermolecular hydrogen bonding. In fact, phenols tend to form stronger hydrogen bonds than alcohols. Hydrogen bonding results in higher melting points and much higher boiling points for phenols than for hydrocarbons with similar molecular weights. Phenols when reacted with $NaOH$ forms sodium phenoxide. Phenol is acidic in nature because on releasing ${H^ + }$ ion it forms a resonance stabilized phenoxide. Carboxylic acid is more acidic than phenol. Acid releasing ${H^ + }$ ion forms carboxylate which is more stable than phenoxide. Carboxylate ions have equally contributing resonating structures.

Correct answer is option C.

Note:
We must have to know that the negative charge is delocalized on the negatively charged $O$ atom thus it is more stable than phenoxide. Hence phenol is a weak acid compared to carboxylic acid. \[NaHC{O_3}\] is a weak base that reacts only with a strong acid like carboxylic acid and does not react with a weak acid like phenol.