CHEM 2332H Lecture Notes - Opata Language, Sodium Nitrate, Azo Compound

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15 Jul 2014
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-> ortho/para directing here, n2 doesn"t get kicked out azo dyes. These above rxns show up in multistep synthesis: put nitrate on aromatic ring, reduce to amine, turn into diazo, substitute (with the above rxns) Mechanism: goes through aryl cation (very rare, need leaving group like n2 to get to this) The plane of the cation"s orbital is in the plane of the page while the aromatic orbitals are into/out of page. That"s why wants nucleophilic attack on +charged central c to relieve that strain. If had stronger ortho para directing group para to ch3, then can make cl go ortho to it. If just to electrophilic aromatic substitution, then prefers ortho/para, so not the major product. -> use sacrificial base that"s stronger than byproduct (acid) product. If mix just ammonia and sodium nitrate, will automatically make n2 since it"s not attached to anything else. Nabh4 works just fine as well and more selective might be the better option.

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