Question

What happens when chloroform is subjected to hydrolysis?

Answer 1

When chloroform (CHCl₃) is subjected to hydrolysis, particularly under alkaline conditions (presence of NaOH), it reacts stepwise to form formate ion and chloride ions via a key intermediate called dichlorocarbene (:CCl₂).

1. Hydroxide ion attacks chloroform, abstracting one hydrogen and causing the release of a chloride ion, forming dichlorocarbene:
   \[\mathrm{CHCl}_3 + \mathrm{OH}^- \rightarrow :\mathrm{CCl}_2 + \mathrm{Cl}^- + \mathrm{H}_2\mathrm{O}\]
2. The dichlorocarbene intermediate reacts with hydroxide ions and water to yield formate ion and chloride ions:
   \[:\mathrm{CCl}_2 + 3\mathrm{OH}^- \rightarrow \mathrm{HCOO}^- + 2\mathrm{Cl}^- + \mathrm{H}_2\mathrm{O}\]