Orgo exam 3

  1. Sn2
    • Good nucelophiles, poor bases
    • Anions with conjugate acids of <12
    • Uncharged nonbinding e- on N, P, or S
    • Primary carbons or Methyl groups
    • Will revert stereochem
  2. E2
    • Good bases
    • Conjugate acid >13
    • Hindered uncharged N
    • Primary and Secondary carbons
  3. Sn1 E1
    • Poor nucleophiles, poor bases
    • Neutral molecules that have good conjugate acids
    • Tertiary Carbons
    • Will either retain or revert sterochem
  4. H-X
    • Reagent : H-X and double bond
    • Mechanism : Carbocation
    • Regioselectivity : Markovnikov
    • Stereoselectivity : Syn+Anti

    Ex) H-CL
  5. H/Or
    • Reagent : ROH + Cat Acid 
    • Mechanism : Carbocation
    • Regioselectivity : Markovnikov 
    • Stereoselectivity : Syn + Anti

    Ex) CH3OH + H2SO4
  6. H/OH 1
    • Reagent : H2O + Cat Acid
    • Mechanism : Carbocation
    • Regioselectivity : Markovnikov
    • Stereoselectivity : Syn+Anti
  7. H/OH 2
    • Reagent :  BH3 + H2O2/NaOH
    • Mechanism : no carbocation, BH2-OH
    • Regioselectivity : anti-Markovnikov
    • Stereoselectivity : Syn only
  8. X/X
    • Reagent : X2
    • Mechanism : Via halonium ion ring
    • Regioselectivity : none
    • Stereoselectivity : anti
  9. X/OH
    • Reagent : NBS+H2O, B2+H2O, X-OH
    • Mechanism : Via halonium ino ring
    • Regioselectivity : Markvnikov
    • Stereoselectivity : Anti
  10. X/OR
    • Reagent : NBS + ROH Br2+ROH X-OR (Br-OCH3) 
    • Mechanism : Via Halonium Ion
    • Regioselectivity : Markovnikov 
    • Stereoselectivity : ante
  11. OH/OH
    • Reagent : OsO4 or KmNO4 + NaOH, H2O
    • Mechanism : Binding to double bond
    • Regioselectivity : NA
    • Stereoselectivity : Syn only
  12. Epoxide ring formation
    • Reagent : MCPBA
    • Mechanism : see notes
    • Regioselectivity : NA
    • Stereoselectivity : SYN
  13. Ozonolysis (only reagents)
    Reductive) O3 + DMS or ZN+H2O 

    Oxidative) H2O2
  14. H/H Double bond (Reagents only)
    Reagents : H2 + Pd/C, Pd, PtO2, Pt, Ni
  15. H/H Across triple bond (reagents only)
    Z-Alkene) H2, Pd/CaCo3, Quinoline, Pbo pd/BaSO4

    E-Alkene) Na,NH3 or Li,Nh3
Author
Cloverfield742
ID
318472
Card Set
Orgo exam 3
Description
Orgo
Updated