Among the following which one does not act as an intermediate in Hofmann rearrangement?

Among the following which one does not act as an intermediate in Hofmann rearrangement?
  1. $\mathrm{RNCO}$
  2. $R \mathrm{CO} \ddot{\mathrm{N}}$
  3. $R \mathrm{CON̈HBr}$
  4. $\mathrm{RNC}$

Solution

(ii) $\mathrm{RCONHBr}+\mathrm{KOH} \rightarrow \mathrm{RNCO}+\mathrm{KBr}+\mathrm{H}_2 \mathrm{O}$ (iii) $\mathrm{RNCO}+2 \mathrm{KOH} \rightarrow \mathrm{RNH}_2+\mathrm{K}_2 \mathrm{CO}_3$ $\mathrm{RCONH}_2+\mathrm{Br}_2+4 \mathrm{KOH} \rightarrow \mathrm{RNH}_2+2 \mathrm{KBr}$ $+\mathrm{K}_2 \mathrm{CO}_3+2 \mathrm{H}_2 \mathrm{O}$

Asked in: NEET 2004

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