| Reaction | Example | Comments |
|---|---|---|
| Addition of HX |  |
M's Rule; stereochem (where possible) varies |
| Double addition of HX |  |
M's Rule |
| Hydration |  |
M's Rule; tautomerism |
| Hydroboration |  |
Anti-M; tautomerism |
| Halogenation |  |
Usually (but not always) anti- via halonium ion |
| Double Halogenation |  |
Generally no stereochem |
| Oxidation |  |
Ozonolysis oxidative workup only |
| Hydrogenation |  |
Z-stereoselective |
| Reduction |  |
E-stereoselective |