-
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
-
E2
- Good bases
- Conjugate acid >13
- Hindered uncharged N
- Primary and Secondary carbons
-
Sn1 E1
- Poor nucleophiles, poor bases
- Neutral molecules that have good conjugate acids
- Tertiary Carbons
- Will either retain or revert sterochem
-
H-X
- Reagent : H-X and double bond
- Mechanism : Carbocation
- Regioselectivity : Markovnikov
- Stereoselectivity : Syn+Anti
Ex) H-CL
-
H/Or
- Reagent : ROH + Cat Acid
- Mechanism : Carbocation
- Regioselectivity : Markovnikov
- Stereoselectivity : Syn + Anti
Ex) CH3OH + H2SO4
-
H/OH 1
- Reagent : H2O + Cat Acid
- Mechanism : Carbocation
- Regioselectivity : Markovnikov
- Stereoselectivity : Syn+Anti
-
H/OH 2
- Reagent : BH3 + H2O2/NaOH
- Mechanism : no carbocation, BH2-OH
- Regioselectivity : anti-Markovnikov
- Stereoselectivity : Syn only
-
X/X
- Reagent : X2
- Mechanism : Via halonium ion ring
- Regioselectivity : none
- Stereoselectivity : anti
-
X/OH
- Reagent : NBS+H2O, B2+H2O, X-OH
- Mechanism : Via halonium ino ring
- Regioselectivity : Markvnikov
- Stereoselectivity : Anti
-
X/OR
- Reagent : NBS + ROH Br2+ROH X-OR (Br-OCH3)
- Mechanism : Via Halonium Ion
- Regioselectivity : Markovnikov
- Stereoselectivity : ante
-
OH/OH
- Reagent : OsO4 or KmNO4 + NaOH, H2O
- Mechanism : Binding to double bond
- Regioselectivity : NA
- Stereoselectivity : Syn only
-
Epoxide ring formation
- Reagent : MCPBA
- Mechanism : see notes
- Regioselectivity : NA
- Stereoselectivity : SYN
-
Ozonolysis (only reagents)
Reductive) O3 + DMS or ZN+H2O
Oxidative) H2O2
-
H/H Double bond (Reagents only)
Reagents : H2 + Pd/C, Pd, PtO2, Pt, Ni
-
H/H Across triple bond (reagents only)
Z-Alkene) H2, Pd/CaCo3, Quinoline, Pbo pd/BaSO4
E-Alkene) Na,NH3 or Li,Nh3
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