Unimolecular Nucleophilic Substitution (S N 1): Structural Reactivity Evidenced by Colored Acid–Base Indicators

CAMINOS, DANIEL A.

JOURNAL OF CHEMICAL EDUCATION

AMER CHEMICAL SOC

Año: 2018 vol. 95 p. 1827 - 1827

0021-9584

he different reactivities between 1°, 2°, and 3° butyl chlorides by the unimolecular nucleophilic substitution (SN1) mechanism were easily observed at 60 °C by a solvolysis reaction in ethanol with ether formation. The hydrogen ion from the byproduct HCl reacted with an acid?base indicator such as methyl red to induce a color change. At room temperature, the addition of AgNO3 was used to detect the released chloride ion by AgCl precipitation. The reactivity order (3° > 2° ≫1°) was visually confirmed by both a color change in an indicator and precipitate formation by these safe, quick, and easy assays.