Benzpinacol-Benzpinacolone Rearrangement & The Cannizzarro

Benzpinacol-Benzpinacolone Rearrangement & The Cannizzarro ...

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Benzpinacol-Benzpinacolone  Reaction. Examples of a Rearrangement and of a  Redox Reaction.
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Rearrangements: Most involve an electron-deficient site or a  “Concerted Reaction”. Some involve an electron-rich site with a  leaving group near-by.
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Wagner-Meerwein Rearrangement The W-M rearrangement is the name given to the  1,2-migrations common to carbocations. C C H X C C H -X - C C H 1,2- migration C C R X C C R -X - C C R 1,2- migration
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1,2-Migrations (Wagner-Meerwein) Most Common type of rearangement. Only a significant reaction if it: a. Results in a more stable      carbocation. or  b. Is assisted by an adjacent                electron-donating atom to form      a stable species.
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More stable Carbocation? Two pathways to a more stable  carbocation are: i. 1,2-migration to form a more     substituted carbocation.  ii. 1,2-migration to form a      resonance-delocalized      carbocation.
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Assistance of Neighboring Atom. Assisted migration has the stabilizing benefit of  completing all octets. Donating e -  pair facilitates the migration as well as  completing octets. C R C OH X C R C OH -X - C R C 1,2- migration OH All complete octets
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A pinacol is a vicinal di-tertiary diol (di-alcohol). Treatment with acid, converts one of the hydroxyl 
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This note was uploaded on 07/09/2008 for the course CHM 218 taught by Professor Loeffler during the Fall '08 term at Sam Houston State University.

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Benzpinacol-Benzpinacolone Rearrangement & The Cannizzarro ...

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