Question

Which one the following compounds will readily react with dilute NaOH?

• A. C$_6$H$_5$CH$_2$OH
• B. C$_2$H$_5$OH
• C. (CH$_3$)$_3$COH
• D. C$_6$H$_5$OH

Answer 1

Answer: (D)

C$_6$H$_5$OH

Answer 2

Phenol (C$_6$H$_5$OH) reacts readily with dilute NaOH because it is more acidic than water. The reaction is as follows:
$\text{C}_6\text{H}_5\text{OH} + \text{NaOH} \rightarrow \text{C}_6\text{H}_5\text{O}^- \text{Na}^+ + \text{H}_2\text{O}.$
The phenoxide ion (C$_6$H$_5\text{O}^-$) formed is stabilized by resonance, making phenol a stronger acid than water.