Positive iodoform test :
- All methyl ketones: RCOCH3 (acetone, acetophenone, etc.)
- Acetaldehyde: CH3CHO
- Ethanol: CH3CH2OH (oxidized to CH3CHO → then iodoform)
- Secondary alcohols with methyl: RCH(OH)CH3 (oxidized to RCOCH3)
Negative iodoform:
- Diethyl ketone (CH3CH2COCH2CH3) — no methyl on C=O
- Benzaldehyde (PhCHO) — no methyl on C=O
- 3-Pentanone — no methyl on C=O
- Methanol — oxidized to HCHO, not to a methyl ketone
Mechanism: Base abstracts alpha-H → halogenation of all 3 alpha-H's → CX3 group cleaved by OH- → CHX3 + RCOO-