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Reaction Mechanism:

  1. Diazotization: When an aromatic primary amine reacts with HNO2 it undergoes diazotization to form a highly reactive diazonium ion.
  2. Intramolecular Cyclization:

    Since o-phenylenediamine has two amino groups ortho to each other, one of the $$-\text{NH}_2$$ groups is converted into a diazonium group ($$-\text{N}_2^+$$).

  3. Ring Closure:

    The adjacent, unreacted primary amino group ($$-\text{NH}_2$$) acts as an internal nucleophile. The lone pair on its nitrogen atom attacks the neighboring diazonium group, causing a rapid intramolecular cyclization to close a stable 5-membered heterocyclic ring.

  4. Deprotonation:

    After losing a proton ($$\text{H}^+$$), the stable heterocyclic compound Benzotriazole is formed.

Structure of the Product:

The resulting compound contains a benzene ring fused to a triazole ring (a 5-membered ring containing three nitrogen atoms), with the structure:

  • A benzene core.
  • Fused to a ring containing $$-\text{N}=\text{N}-\text{NH}-$$.

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