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CHEM 2OA3 Lecture Notes - Hydride, Alkyl, Epoxide

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Jeff Landry

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Hydride Shifts
CH3-C(CH3)(H)-C(OH)(H)-CH3 ---HBr→
o EXPECTED: CH3-C(CH2)(H)-C(Br)(H)(CH3)
o ACTUAL: CH3-C(CH3)(Br)-CH2-CH3
o Original had an H+ go to the OH, so H2O split off and you had left a carbocation
(on Carbon-3), which then pulls the hydrogen on Carbon-2 to its new empty
space, making a new carbocation (Carbon-2), which then pulls the Br
Secondary to Tertiary Shift
The Hydrogen doesn’t “jump,” it’s a smooth transfer (orbitals have to line
up correctly)
Won’t have to give a product and have to “anticipate” a Hydride Shift occurring
o We WILL have to be able to recognize it he gives us the reactant, condition, AND
the product
CH3-C(CH3)2-C(OH)(H)-CH3 ---HBr→
o EXPECTED: CH3-C(CH3)2-C(Br)(H)-CH3
o ACTUAL: CH3-C(CH3)(Br)-C(CH3)(H)-CH3
o The OH got an H+ and broke off as H2O, leaving the carbocation (C-3). The CH3
connected to the Carbon-2 shifts to the Carbon-3, leaving Carbon-2 as a
carbocation. Br- connects to the C-2 carbocation.
Almost ANY Alkyl group can undergo this shift
Smaller groups move faster
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