Chem357_NBS___Grignards____FINAL_student_

Chem357_NBS___Grignards____FINAL_student_ - Radical...

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1 Br N O O Br H Br + N O O H Br Br + N O O Br Mechanism: peroxide N O O Br + Br H H Br Ionic reaction Thoughts on how this reaction might proceed? Radical Radical Bromination Bromination of of Allylics Allylics using NBS using NBS 2 Radical Radical Bromination Bromination of of Allylics Allylics using NBS using NBS Where is the most B A S I C center in the molecule? N O O Br
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3 Radical Radical Bromination Bromination of of Allylics Allylics using NBS using NBS N O O Br H Br + N O O H Br Br + Where is the most B A S I C center in the molecule? N O O Br Br + H N O O Br H N O O Br H Br + N O O H Br OPTION A OPTION B N O O H Tautomerization 4 N O O Br N O O Br N O O Br N O O Br ! + ! - ! - HYBRID Could we have predicted based on the structure of the base? When a carbonyl containing molecule is treated with acid, usually the carbonyl is protonated. O H + O H O H N H O H + N H O H N H O H N H O H A L O K F R W D Radical Radical Bromination Bromination of of Allylics Allylics using NBS using NBS
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Chem357_NBS___Grignards____FINAL_student_ - Radical...

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