[\ce{KCN}][\text{benzene}]CH3(CH2)8CH2CN}$$The options are (A) benzyl chloride (B) aniline (C) N,N,N-trimethylbenzylamine chloride, and (D) N-phenylethanamide.Now, at first, I immediately thought that the catalyst chosen may have to prevent a possible ring formation, given there are already ten carbon atoms. However, I am not sure how any of those catalysts help prevent that (I doubt if a ring would even form thoug">
[\ce{KCN}][\text{benzene}]CH3(CH2)8CH2CN}$$The options are (A) benzyl chloride (B) aniline (C) N,N,N-trimethylbenzylamine chloride, and (D) N-phenylethanamide.Now, at first, I immediately thought that the catalyst chosen may have to prevent a possible ring formation, given there are already ten carbon atoms. However, I am not sure how any of those catalysts help prevent that (I doubt if a ring would even form thoug">
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How do quaternary ammonium salts catalyse SN2 reactions?
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Miguel
How do quaternary ammonium salts catalyse SN2 reactions?
Trimethylbenzylammonium chloride is in this reaction a good example of a phase transfer catalyst. It first forms the trimethylbenzylammonium cyanide in aqueous phase (or on the surface of solid phase) which is soluble in the organic phase. Because of the polar nature of the cyanide ion it is not going to be heavily solvated by organic solvent (in this case benzene) molecules so the result is 'naked' cyanide which is highly reactive. This reacts with the substrate forming, in this case, the cyanodecane and trimethylbenzylammonium bromide. The trimethylbenzylammonium bromide is then free to migrate back to the aqueous phase and exchange anion to reform trimethylbenzylammonium cyanide. Most phase transfer reactions benefit from vigorous stirring to accelerate the exchange between the phases.
Trimethylbenzylammonium chloride is in this reaction a good example of a phase transfer catalyst. It first forms the trimethylbenzylammonium cyanide in aqueous phase (or on the surface of solid phase) which is soluble in the organic phase. Because of the polar nature of the cyanide ion it is not going to be heavily solvated by organic solvent (in this case benzene) molecules so the result is 'naked' cyanide which is highly reactive. This reacts with the substrate forming, in this case, the cyanodecane and trimethylbenzylammonium bromide. The trimethylbenzylammonium bromide is then free to migrate back to the aqueous phase and exchange anion to reform trimethylbenzylammonium cyanide. Most phase transfer reactions benefit from vigorous stirring to accelerate the exchange between the phases.
Interesting, thanks for your answer! Can you comment on why the other options are not good examples of phase transfer catalysts? Is it possible to compare this property theoretically? Also, which page was I supposed to read in that PDF?More
Benzyl Chloride - not good as it is an alternative substrate for the nucleophile. Aniline and phenylethanamide - not good as it is not soluble in aq. phase or able to draw cyanide ions into solution from solid phase. Section 1.2.3 of the PDF mentions the concept of the naked ion. I am not aware of any theoretical model to predict PT catalytic property - this does not mean it does not existMore
Trimethylbenzylammonium chloride is in this reaction a good example of a phase transfer catalyst. It first forms the trimethylbenzylammonium cyanide in aqueous phase (or on the surface of solid phase) which is soluble in the organic phase. Because of the polar nature of the cyanide ion it is not going to be heavily solvated by organic solvent (in this case benzene) molecules so the result is 'naked' cyanide which is highly reactive. This reacts with the substrate forming, in this case, the cyanodecane and trimethylbenzylammonium bromide. The trimethylbenzylammonium bromide is then free to migrate back to the aqueous phase and exchange anion to reform trimethylbenzylammonium cyanide. Most phase transfer reactions benefit from vigorous stirring to accelerate the exchange between the phases.
Further reading in this PDF.
Trimethylbenzylammonium chloride is in this reaction a good example of a phase transfer catalyst. It first forms the trimethylbenzylammonium cyanide in aqueous phase (or on the surface of solid phase) which is soluble in the organic phase. Because of the polar nature of the cyanide ion it is not going to be heavily solvated by organic solvent (in this case benzene) molecules so the result is 'naked' cyanide which is highly reactive. This reacts with the substrate forming, in this case, the cyanodecane and trimethylbenzylammonium bromide. The trimethylbenzylammonium bromide is then free to migrate back to the aqueous phase and exchange anion to reform trimethylbenzylammonium cyanide. Most phase transfer reactions benefit from vigorous stirring to accelerate the exchange between the phases.
Further reading in this PDF.
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