Named Reactions Quick Reference
| Reaction | Reagent | Product | Key Point |
|---|---|---|---|
| HVZ | X2/Red P | alpha-halocarboxylic acid | Needs alpha-H; not for HCOOH/ArCOOH |
| Fischer esterification | R'OH/H2SO4 | RCOOR' + H2O | Reversible; K ≈ 1 |
| Saponification | NaOH/H2O | RCOONa + R'OH | Irreversible; gives salt |
| Decarboxylation | NaOH+CaO/heat | R–H + Na2CO3 | Removes –COOH; loses 1 C |
| Kolbe electrolysis | Electrolysis of RCOO– | R–R + CO2 | Anode; symmetrical alkane |
| Grignard carboxylation | RMgX + CO2 | RCOOH | Anhydrous; adds 1 C |
| LiAlH4 reduction | LiAlH4/dry ether | RCH2OH | NaBH4 fails |
| SOCl2 acyl chloride | SOCl2 | RCOCl + SO2 + HCl | Gaseous byproducts = clean |
| PCl5 acyl chloride | PCl5 | RCOCl + POCl3 + HCl | Liquid POCl3 = messy |
| Nitrile hydrolysis | H3O+/reflux | RCOOH + NH4+ | Acid conditions |
Key pKa Data
| Compound | SMILES | pKa |
|---|---|---|
| Trichloroacetic acid (Cl3CCOOH) | OC(=O)C(Cl)(Cl)Cl | 0.65 |
| Dichloroacetic acid (Cl2CHCOOH) | OC(=O)C(Cl)Cl | 1.26 |
| Monochloroacetic acid (ClCH2COOH) | OC(=O)CCl | 2.87 |
| Formic acid (HCOOH) | OC=O | 3.75 |
| Acetic acid (CH3COOH) | CC(=O)O | 4.76 |
| Trimethylacetic acid ((CH3)3CCOOH) | — | 5.05 |
| Phenol | — | ~10 |
| Water | — | 15.7 |
| Ethanol | — | ~16 |
| Terminal alkyne | — | ~25 |