Diazonium Salts

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Diazonium Salts. Diazonium: there are 2 nitrogen atoms joined together in the positive ion. In French, nitrogen is still called by its old name ‘azote’ which means unable to support life. Diazonium Salts. Notice the triple bond between the nitrogen atoms
Transcript
Diazonium Salts
  • Diazonium: there are 2 nitrogen atoms joined together in the positive ion.
  • In French, nitrogen is still called by its old name ‘azote’ which means unable to support life.
  • Diazonium Salts
  • Notice the triple bond between the nitrogen atoms
  • The positive charge is on the nitrogen that is attached to the benzene ring
  • Why are they important? They look pretty weird!
  • They are essential in the dye industry.
  • A Diazonium salt is produced then reacted with a phenol. If the correct phenol is used, almost any colour can be produced.
  • OCR specify this as a reaction you need to know.
  • In the last CRS paper, this was a question worth 6 marks! Very few students got many marks at all.
  • Formation of the Diazonium salt.
  • Formed by reacting phenylamine with sodium nitrite and hydrochloric acid.
  • These reagents form in situ nitrous acid HONO.
  • Formation of the Diazonium salt.
  • The Diazonium salt is unstable above 10°C, so the reaction is normally carried out in ice.
  • An aliphatic Diazonium salt is very unstable, so only aromatics are used.
  • The lone pairs present in the salt can participate in the benzene ring, making it more stable. More correctly this is due to overlap of p-orbitals in the diazo group with the p-system in the ring.
  • So phenylamine would give benzenediazonium chloride.
  • Formation of the Diazonium salt.Formation of the Diazonium salt.
  • The conditions are 5°C and remember the HONO (nitrous acid) is prepared in situ by reacting sodium nitrite with hydrochloric acid.
  • The diazonium salt can ten do one of two things depending on the temperature
  • Reactions of aromatic diazonium saltsHydrolysis
  • The following occurs if a solution of a diazonium salt is warmed up:
  • Coupling reactions
  • The mechanism is for interest only, you do not need to know it.
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