Haloform / Iodoform Reaction

Rarely Tested

$$\text{R-CO-CH}_3 + 3\text{X}_2 + 4\text{NaOH} \longrightarrow \text{CHX}_3 \downarrow + \text{R-COO}^-\text{Na}^+ + 3\text{NaX} + 3\text{H}_2\text{O}$$

Concept: Oxidative cleavage of a carbon-carbon bond triggered by successive halogenation of a terminal methyl group under basic conditions. The reaction acts as a standard qualitative test because the trihalomethane byproduct separates as a distinct solid phase.

Notation:

  • $$\text{Methyl Ketones / 2-ols}$$ = Active groups like $$\text{R-CO-CH}_3$$ , ethanol, or secondary methyl alcohols;
  • $$\text{CHI}_3$$ = Triiodomethane, forming a signature bright yellow precipitate.
Question 1

Natural rubber on complete ozonolysis ($$\mathrm{O_3}$$/Zn-$$\mathrm{H_2O}$$) gives compound X as the major product. X gives positive iodoform and Tollen's tests. X on heating with aqueous NaOH gives Y as the major product. Y is

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