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08-01 - Hydride Shifts, Ether Chemistry, Epoxide Formation.docx

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McMaster University
Jeff Landry

Hydride Shifts  CH -3(CH )(H3-C(OH)(H)-CH ---HBr→ 3 o EXPECTED: CH -C(CH )(3)-C(Br)2H)(CH ) 3 o ACTUAL: CH -C(CH )(Br)-CH -CH 3 3 2 3 o Original had an H go to the OH, so H O split2off 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  CH -3(CH ) -3 2H)(H)-CH ---HBr→3 o EXPECTED: CH -C(CH ) -C(Br)(H)-CH 3 3 2 3 o ACTUAL: CH -C(CH )3Br)-C(C3 )(H)-CH 3 3 + o The OH got an H and broke off as H O, leavi2g the carbocation (C-3). The CH 3 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 Ether Chemistry  Ether: C-O-C (R-O-R) (partial positive on the carbons, partial negative on oxygen) o Stable C-O bond (stable, not very reactive) o Sometimes use it as solvents because it doesn’t react much o Pretty much only react with strong acids  E.g. CH 3O-C(CH ) =3 3Butyl Methyl Ether  E.g. CH 3CH -2-(Cyclohexane) = Cyclohexyl Ethyl Ether  Cyclohexane-OCH = Methoxy cyclohexane (uns
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