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Reaction List - Ch 12 Reactions of Alkenes (II) A d d i t i o n o f X 2 A d d i t i o n o f X 2 w i t h H 2 O C a t a l y t i c H y d r o g e n a t i o n H y d r o x y l a t i o n H 2 Pd/C H adds to both sides of C=C excess hydrogen is always present syn addition alkane KMnO 4 H 2 O, NaOH OH OH OH is added to both sides of C=C syn addition OsO 4 H 2 O 2 or halogen is added to both sides of C=C Cl 2 or Br 2 may be used (diiodides are not very stable) anti addition Br 2 Br Br vicinal diol vicinal dihalide OH is added to more substituted side, halogen to less Cl 2 , Br 2 , or I 2 may be used anti addition Br 2 OH Br H 2 O halohydrin

Reaction List Ch12

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  • Reaction List - Ch 12Reactions of Alkenes (II)

    Addition of X2

    Addition of X2 with H2O

    Catalytic Hydrogenation

    Hydroxylation

    H2

    Pd/C

    H adds to both sides of C=Cexcess hydrogen is always presentsyn addition

    alkane

    KMnO4

    H2O, NaOHOH

    OH

    OH is added to both sides of C=Csyn addition

    OsO4

    H2O2

    or

    halogen is added to both sides of C=C

    Cl2 or Br2 may be used (diiodides are not very stable)

    anti addition

    Br2Br

    Br

    vicinal diol

    vicinal dihalide

    OH is added to more substituted side, halogen to less

    Cl2, Br2, or I2 may be used

    anti addition

    Br2 OH

    Br

    H2O

    halohydrin

  • Cyclopropanation

    Polymerization

    Oxidative cleavage:

    Epoxidation

    O

    OPhOH

    +O

    reagent may be abbreviated PhCO3H

    syn addition

    CH2N2

    heat or light

    orCH2I2

    Zn, CuCl

    CHBr3

    (CH3)3COK

    Br

    Br

    carbene is formed in each casesyn addition

    orH2SO4 ROOR

    heat or light

    acid creates carbocation; peroxide creates radicalcarbocation or radical react with another alkene

    O3

    O3

    (CH3)2S

    H2O2

    O

    O

    HH

    O

    O

    OHH

    epoxide

    cyclopropane

    polymer

    aldehydes and/or ketones

    carboxylic acids and/or ketones

    cyclic compounds give dicarbonyl compoundsif the C=C is symmetrical, only one product is formed