Diazonium_Coupling_Reaction

Diazonium_Coupling_Reaction - CO 2 H NH 2 N + O N a N O 2 ,...

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Click to edit Master subtitle style 5/13/09 Diazonium Coupling Reaction CH 222L April 23, 2009
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5/13/09 Diazonium Coupling Reaction Form and use a diazonium salt in a diazo coupling reaction Produce an azobenzene derivative (azo dye) General Reaction CO 2 H NH 2 CO 2 H N N + N N N N CO 2 H Cl- + N a N O 2 H C l H 2 O 0 C Anthranilic Acid Anthranyl diazonium chloride N, N - dimethyl - aniline Methyl Red
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5/13/09 First need to form nitrosyl cation to act as nucleophile Reaction Mechanism N O O - N + O H N O O H H N O + O H 3 O + H 3 O + - H 2 O Nitrite ion (from sodium nitrite) Nitrous acid Nitrosyl cation
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5/13/09 Reaction Mechanism Anthranilic acid attacks the nitrosyl cation forming the aryl diazonium ion
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Unformatted text preview: CO 2 H NH 2 N + O N a N O 2 , H C l H 2 O , 0 * C H H O N CO 2 H N + O H 2 H O N CO 2 H N H 3 O + H OH + N CO 2 H N OH N CO 2 H N OH 2 N CO 2 H N N CO 2 H N + Cl-O H 2 H 3 O + H 2 O + 5/13/09 Reaction Mechanism The aryl diazonium ion, a weak electrophile attacks the strongly activated aromatic ring N CO 2 H N + Cl-H 2 O + + N N N N CO 2 H H N + N N CO 2 H Cl-HCl + Methyl Red 5/13/09 Diazonium Ion Reactions Fig 22.5 on pg 938 is VERY HELPFUL Remember: NO2 is META directing and NH2 is ORTHO/PARA directing...
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Diazonium_Coupling_Reaction - CO 2 H NH 2 N + O N a N O 2 ,...

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