All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone. H,SO, OOH OH + O= Cumene Phenol Acetone hydroperoxide
All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone. H,SO, OOH OH + O= Cumene Phenol Acetone hydroperoxide
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.65P: All rearrangements we have discussed so far have involved generation of an electron-deficient carbon...
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