CHEM 301
Quiz yourself by thinking what should be in
each of the black spaces below before clicking
on it to display the answer.
Help!
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| Addition of HX | Add. Reagents: HX
What adds? -H, -X
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? yes
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| Addition of HBr with H2O2 | Add. Reagents: HBr, peroxide
What adds? -H, -Br
Regioselectivity: Anti-Markovnikov
Stereoselectivity: n/a
Rearrangement possible? no
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| Acid-Catalyzed Hydration | Add. Reagents: H2O, H+
What adds? -H, -OH
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? yes
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| Oxymercuration-Demercuration | Add. Reagents: 1) Hg(OAc)2, H2O, 2)NaBH4
What adds? -H, -OH
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? no
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| Alkoxymercuration-Demercuration | Add. Reagents: 1) Hg(OAc)2, ROH, 2)NaBH4
What adds? -H, -OR
Regioselectivity: Markovnikov
Stereoselectivity: n/a
Rearrangement possible? no
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| Hydroboration-Oxidation | Add. Reagents: 1) BH3, 2) H2O2, -OH
What adds? -H, -OH
Regioselectivity: Anti-Markovnikov
Stereoselectivity: syn
Rearrangement possible? no
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| Hydrogenation | Add. Reagents: H2 and Pt, Pd, or Ni
What adds? -H, -H
Regioselectivity: n/a
Stereoselectivity: syn
Rearrangement possible? no
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| Simmons-Smith | Add. Reagents: CH2I2, Zn(Cu)
What adds? -CH2-
Regioselectivity: n/a
Stereoselectivity: retention of stereochemistry
Rearrangement possible? no
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| 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
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| Addition of halogens | Add. Reagents: X2, inert solvent
What adds? -X, -X
Regioselectivity: n/a
Stereoselectivity: anti
Rearrangement possible? no
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| Halohydrin Formation | Add. Reagents: X2, H2O
What adds? -X, -OH
Regioselectivity: -OH to more substituted side
Stereoselectivity: anti
Rearrangement possible? no
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| Epoxidation | Add. Reagents: R-CO3H
What adds? -O-
Regioselectivity: n/a
Stereoselectivity: retention of stereochemistry
Rearrangement possible? no
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| Epoxidation + Ring Opening | Add. Reagents: R-CO3, H+ (aq)
What adds? -OH, -OH
Regioselectivity: n/a
Stereoselectivity: anti
Rearrangement possible? no
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| Osmium Tetroxide | Add. Reagents: OsO4
What adds? -OH, -OH
Regioselectivity: n/a
Stereoselectivity: syn
Rearrangement possible? no
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| KMnO4 (mild) | Add. Reagents: KMnO4 (mild)
What adds? -OH, -OH
Regioselectivity: n/a
Stereoselectivity: syn
Rearrangement possible? no
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| 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
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| KMnO4 (vigorous) | Add. Reagents: KMnO4 (vigorous)
What adds? n/a
Regioselectivity: splits the bond
Stereoselectivity: further oxidizes aldehydes
Rearrangement possible? to COOH
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