Named reactions of phenol constitute a consistent NEET topic. All three major reactions exploit the activated nature of the phenol ring.
1. Kolbe Reaction (Kolbe-Schmitt Carboxylation):
- Substrate: sodium phenoxide (NOT phenol directly)
- Reagent: under pressure
- Conditions: 125°C, 4-7 atm
- Product: salicylic acid (
SMILES:OC(=O)c1ccccc1O) — -COOH at ortho position - Significance: salicylic acid → acetylation → aspirin (acetylsalicylic acid)
2. Reimer-Tiemann Reaction (Formylation):
- Substrate: phenol
- Reagent: + NaOH
- Intermediate: dichlorocarbene (:) — electrophilic, attacks phenoxide at ortho position
- Product: salicylaldehyde (
SMILES:O=Cc1ccccc1O) — ortho-hydroxybenzaldehyde
3. Bromination of Phenol:
- No Lewis acid catalyst () required — unlike benzene
- Product: white crystalline precipitate
- Also serves as qualitative test for phenol
Summary Comparison:
| Reaction | Reagent | Product | Position |
|---|---|---|---|
| Kolbe | , pressure | Salicylic acid (-COOH) | Ortho |
| Reimer-Tiemann | /NaOH, : | Salicylaldehyde (-CHO) | Ortho |
| Bromination | /, no catalyst | 2,4,6-tribromophenol | O, O, P |