Why will the reaction fail to work if the phase transfer catalyst is switched to ammonium chloride while retaining the same reactants, solvent, and base? Because it reacts with 2‑naphthol to make 2‑chloronaphthalene. Because it generates a powerful nitrogen‑based nucleophile in aqueous base. Because ammonium chloride is not soluble in dichloromethane solvent. Because ammonium chloride is not soluble in water.

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Chemistry

Phoebe Clay

2 March, 15:08

Why will the reaction fail to work if the phase transfer catalyst is switched to ammonium chloride while retaining the same reactants, solvent, and base? Because it reacts with 2‑naphthol to make 2‑chloronaphthalene. Because it generates a powerful nitrogen‑based nucleophile in aqueous base. Because ammonium chloride is not soluble in dichloromethane solvent. Because ammonium chloride is not soluble in water.

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Sean Mcguire · Answer 1

It must be said that methylene chloride and ammonium chloride are polar compounds, however, the reaction stops if ammonium chloride is used as a catalyst, it is already characterized as being a strong Lewis base, thus producing AlCl4⁻ in the presence of chloride ions.