mitan leaning The Williamson ether synthesis between 2-naphthol and allyl bromid

Question

mitan leaning The Williamson ether synthesis between 2-naphthol and allyl bromide in the presence of strong base and benzyltriphenylammonium chloride as a phase transfer catalyst in dichloromethane solution is known to proceed in reasonable yield. OH NaOH Br, PhCH, Ba),NCi naphthol allyl bromide allyl 2-naphthyl ether 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? O Because ammonium chloride is not soluble in water. O Because it generates a powerful nitrogen-based nucleophile in aqueous base. O Because it reacts with 2-naphthol to make 2-chloronaphthalene O Because ammonium chloride is not soluble in dichloromethane solvent

Explanation / Answer

phase tranfer catalyst should soluble in both organic and aq. phase.

Benzyl triphenyl ammoniumchloride is soluble in both DCM and water.

where as ammoium chloride is only soluble in water and insoluble in DCM (organic).

Hence it could not be used as PTC

answer: Ammonium chloride is not soluble in DCM solvent

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