Part of JOC-03 — Aldehydes, Ketones & Carboxylic Acids

Iodoform Reaction — Diagnostic Test

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Positive iodoform test yellowCHI3precipitatewithI2NaOH\frac{yellow CHI3 precipitate with I2}{NaOH}:

  1. All methyl ketones: RCOCH3 (acetone, acetophenone, etc.)
  2. Acetaldehyde: CH3CHO
  3. Ethanol: CH3CH2OH (oxidized to CH3CHO → then iodoform)
  4. 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-

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