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

Chemistry
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Chapter1: Chemical Foundations
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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
Transcribed Image Text: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
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