H HBr Br H HBr H Br Br - University of Texas at...

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  • Reaction:

    H

    Br

    HBr

    H

    Br

    HBr

    Add a proton

    H Br

    Make-a-bond

    1

  • Reaction:

    HBr

    1) Add a proton--but where?

    H

    Br

    H Br

    H Br

    Make-a-bond

    Make-a-bond

    Br

    Br

    Regiochemistry: Markovnikov's Rule

    2

  • Reaction:

    HOH

    H

    OH

    H2SO4catalytic

    First-consider the acid/water reaction:

    H

    OH

    Make-a-bond

    Add a proton

    (protonate)

    Remove a proton

    (deprotonate)

    H2SO4 HOH+

    3

  • Reaction:

    HOH

    OH

    H2SO4catalytic

    H

    Regiochemistry: Markovnikov's Rule

    Make-a-bond

    Add a proton

    (protonate)

    Remove a proton

    (deprotonate)

    OH H

    4

  • Reaction:

    HOH

    HO

    H2SO4catalytic

    H

    Make-a-bond

    Add a proton

    (protonate)

    Remove a proton

    (deprotonate)

    HOH

    1,2 Hydride shif t

    5

    Note: rearrangement

  • Reaction:

    HOH

    HO

    H2SO4catalytic

    CH3 H

    Make-a-bond

    Add a proton

    (protonate)

    Remove a proton

    (deprotonate)

    HOH

    1,2 Methyl shif t

    6

    Note: rearrangement

    CH3

    CH3CH3

  • 7

    Reaction:

    Br2

    CH2Cl2

    Stereochemistry: trans addition

    Br

    Br

    Br

    Br

    Br Br

    Make-a-bond Make-a-bond

    ONLY trans

    Bromonium Ion

  • 8

    Reaction:

    Br2

    H2O

    Stereochemistry: trans addition

    Br

    OH

    Br

    OH

    Br Br

    Make-a-bond

    Make-a-bond

    ONLY trans

    Bromonium Ion

    HO

    Br

    Oxonium Ion

    Remove a proton(deprotonate)

  • 9

    Reaction:

    Br2

    H2O

    Stereochemistry: trans additionOH

    Br

    Br Br

    Make-a-bond

    Make-a-bond

    Bromonium Ion Oxonium Ion

    Remove a proton(deprotonate)

    CH3

    CH3

    CH3

    Regiochemistry: OH to the

    MOST hindered Carbon

    OH

    Br

    CH3

    CH3

    Br

  • 10

    Reaction:

    H removes

    the HgMake-a-bond

    Remove a proton

    (deprotonate)

    H

    Mercurinium ion

    OH

    1) Hg(OAc)2 (aq)

    2) NaBH4

    OH

    H

    Regiochemistry: Markovnikov's Rule

    NO rearrangement

    2) NaBH4

    Make-a-bond

  • 11

    Reaction:

    several steps

    (don't need to know)

    Make-a-bond

    Organoborane Compound

    1) BH3

    2) H2O2NaOH

    Regiochemistry: NON-Markovnikov's Rule

    NO rearrangement

    2) H2O2NaOH

    add B to the least hindered C;Hydride adds syn

    H

    OH

    Stereochemistry:

    SYN addition of H2O

    H

    OH

  • 12

    Reaction:

    several steps

    (don't need to know)

    Make-a-bonds

    Osmate Ester

    1) OsO4

    2) NaHSO3 (aq)

    2) NaHSO3

    OsO4 adds both O atom

    simultaneously

    OH

    OH

    Stereochemistry:

    SYN oxidation

    OH

    OH

    Glycols are the product

    Os

    OO

    OO

    S

    O

    OHONa

    Sodium bisulfite

  • 13

    Reaction:

    several steps

    (don't need to know)

    Make-a-bonds

    Molozonide

    1) O3

    2) (CH3)2S

    2) (CH3)2S

    O3 adds

    simultaneously

    CH3

    CH3

    O

    O

    C---C bonds are

    broken

    Ketones & aldehydes are products

    O

    O

    O

    H

    CH3

    O

    O

    H


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