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Alkene Addition Reactions by Increasing Electronegativity of
Added Reagent
| Atoms Added |
Name |
Reagents |
Regiochemistry |
Stereochemistry |
Subsequent Reactions |
| B, H |
Hydroboration |
diborane |
anti-Markovnikov |
syn |
Oxidation (H2O2, NaOH)
Net anti-Markovnikov Addition of Water |
| H, H |
Hydrogenation |
hydrogen, transition metal |
n/a |
syn |
n/a |
| C: |
Carbene Addition |
diazomethane, chloroform, CH2I2/Zn |
n/a |
syn |
n/a |
| C C |
Cycloadditions |
|
|
|
|
| H, O |
Hydration, Ether Synthesis |
acid, water or alcohols |
Markovnikov |
anti? |
n/a |
| Hg, O |
Oxymercuration |
Hg2+ |
Markovnikov? |
anti |
Reduction (NaBH4)
Net Markovnikov Addition of Water |
| H, X |
Hydrohalogenation |
mineral acid |
Markovnikov |
anti? |
n/a |
| Br., H. |
Bromine Radical Addition |
hydrogen bromide, peroxide |
anti-Markovnikov |
n/a |
n/a |
| O |
Epoxidation |
peracid |
n/a |
syn |
Ring Opening with H3O+
Gives Anti Vicinal Diols |
| O, O |
Dihydroxylation |
osmium tetraoxide, potassium permanganate (Baeyer
Test) |
n/a |
syn |
n/a |
| O3 |
Ozonolysis |
ozone |
n/a |
syn |
Ring Opening, Addition, Reduction (Zn) |
| X, O |
Halohydrin or Haloether Synthesis |
halogen, water |
Markovnikov? |
anti |
Epoxidation (NaOH) |
| X, X |
Halogenation |
halogen |
n/a |
anti |
n/a |
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