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Select a starting functional group and a reagent to predict the product. Learn the mechanism and selectivity for each transformation.
| From | Reagent | To | Mechanism |
|---|---|---|---|
| Alkene | HBr (no peroxides) | Alkyl Halide | Electrophilic Addition |
| Alkene | HBr + ROOR (peroxides) | Alkyl Halide | Radical Chain |
| Alkene | H₂O / H₂SO₄ | Alcohol | Electrophilic Addition |
| Alkene | BH₃·THF, then H₂O₂/NaOH | Alcohol | Concerted + Oxidation |
| Alkene | Br₂ / CCl₄ | Alkyl Halide | Electrophilic Addition |
| Alkene | H₂ / Pd/C | Alkane | Heterogeneous Catalysis |
| Alkene | OsO₄ / NMO (or KMnO₄ cold) | Alcohol | Concerted [3+2] |
| Alkene | mCPBA | Epoxide | Concerted |
| Alkene | O₃, then DMS (or Zn) | Aldehyde | Concerted + Cleavage |
| Alcohol | H₂SO₄, heat | Alkene | E1 or E2 |
| Alcohol | PCC / CH₂Cl₂ | Aldehyde | Cr(VI) Oxidation |
| Alcohol | CrO₃/H₂SO₄ (Jones reagent) | Carboxylic Acid | Cr(VI) Oxidation |
| Alcohol | NaH, then R-X (1° halide) | Ether | SN2 |
| Alcohol | SOCl₂ / pyridine | Alkyl Halide | SNi or SN2 |
| Aldehyde | NaBH₄ / MeOH | Alcohol | Nucleophilic Addition (H⁻) |
| Ketone | NaBH₄ / MeOH | Alcohol | Nucleophilic Addition (H⁻) |
| Aldehyde | RMgBr (Grignard), then H₃O⁺ | Alcohol | Nucleophilic Addition |
| Ketone | RMgBr (Grignard), then H₃O⁺ | Alcohol | Nucleophilic Addition |
| Ketone | H₂NNH₂, KOH, 200°C | Alkane | Hydrazone Decomposition |
| Ketone | mCPBA (peracid) | Ester | 1,2-Shift |
Showing 20 of 34 rules. Use the predictor above to explore all.