Question | Answer |
Addition of HX | Add. Reagents: HX
What adds? -H, -X
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? yes |
Addition of HBr with H2O2 | Add. Reagents: HBr, peroxide
What adds? -H, -Br
Regioselectivity: Anti-Markovnikov
Stereoselectivity: n/a
Rearrangement possible? no |
Acid-Catalyzed Hydration | Add. Reagents: H2O, H+
What adds? -H, -OH
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? yes |
Oxymercuration-Demercuration | Add. Reagents: 1) Hg(OAc)2, H2O, 2)NaBH4
What adds? -H, -OH
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? no |
Alkoxymercuration-Demercuration | Add. Reagents: 1) Hg(OAc)2, ROH, 2)NaBH4
What adds? -H, -OR
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? no |
Hydroboration-Oxidation | Add. Reagents: 1) BH3, 2) H2O2, -OH
What adds? -H, -OH
Regioselectivity: Anti-Markovnikov
Stereoselectivity: syn
Rearrangement possible? no |
Hydrogenation | Add. Reagents: H2 and Pt, Pd, or Ni
What adds? -H, -H
Regioselectivity: n/a
Stereoselectivity: syn
Rearrangement possible? no |
Simmons-Smith | Add. Reagents: CH2I2, Zn(Cu)
What adds? -CH2-
Regioselectivity: n/a
Stereoselectivity: retention of stereochemistry
Rearrangement possible? no |
alpha-elimination | Add. Reagents: CH2X2 or CHX3 w/ strong base
What adds? -CHX- or -CX2-
Regioselectivity: n/a
Stereoselectivity: retention of stereochemistry
Rearrangement possible? no |
Addition of halogens | Add. Reagents: X2, inert solvent
What adds? -X, -X
Regioselectivity: n/a
Stereoselectivity: anti
Rearrangement possible? no |
Halohydrin Formation | Add. Reagents: X2, H2O
What adds? -X, -OH
Regioselectivity: -OH to more substituted side
Stereoselectivity: anti
Rearrangement possible? no |
Epoxidation | Add. Reagents: R-CO3H
What adds? -O-
Regioselectivity: n/a
Stereoselectivity: retention of stereochemistry
Rearrangement possible? no |
Epoxidation + Ring Opening | Add. Reagents: R-CO3, H+ (aq)
What adds? -OH, -OH
Regioselectivity: n/a
Stereoselectivity: anti
Rearrangement possible? no |
Osmium Tetroxide | Add. Reagents: OsO4
What adds? -OH, -OH
Regioselectivity: n/a
Stereoselectivity: syn
Rearrangement possible? no |
KMnO4 (mild) | Add. Reagents: KMnO4 (mild)
What adds? -OH, -OH
Regioselectivity: n/a
Stereoselectivity: syn
Rearrangement possible? no |
Ozonolysis | Add. Reagents: 1) O3, 2) DMS (or something else)
What adds? n/a
Regioselectivity: splits bond, turns into carbonyl
Stereoselectivity: n/a
Rearrangement possible? n/a |
KMnO4 (vigorous) | Add. Reagents: KMnO4 (vigorous)
What adds? n/a
Regioselectivity: splits the bond
Stereoselectivity: further oxidizes aldehydes
Rearrangement possible? to COOH |