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Ch. 8

CHEM 301

QuestionAnswer
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
Created by: slb23310