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can anyone show me the mechanism of the reactions(arrow) chloroform + benzyltriethylammonium chloride + sodium hydroxide?

can anyone show me the mechanism of the reactions(arrow)

chloroform + benzyltriethylammonium chloride + sodium hydroxide?

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Answer #1

Benzyltriethylammonium chloride functions as phase transfer catalyst. The chloride is soluble in basic aqueous phase and is converted into benzyltriethylammonium hydroxide, soluble in organic phase.

The hydroxide ion react with chloroform to give dichlorocarbene with regeneration of benzyltriethylammonium chloride.

Both benzyltriethylammonium chloride and benzyltriethylammonium hydroxide partition between aqueous phase and organic phase(ChCl3). In the aqueous phase benzyltriethylammonium chloride reacts with NaOH to form benzyltriethylammonium hydroxide.

In the Chloroform phase, benzyltriethylammonium hydroxide reacts with CHCl3 to give trichloromethyl anion which eliminates chloride ion to form dichlorocarbene, :CCl2 and benzyltriethylammonium chloride.

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