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標題:

Why C6H5O- is a stronger nucleophile than CH3CO2-?

發問:

Why C6H5O- is a stronger nucleophile than CH3CO2-?

最佳解答:

A stronge nucleophilie which mean it have rich negative center and readly to donates to a positiver center CHeCO2- is a weaker nucleophile than C6H5O- beacause it have 2 oxygen atom to disperse the negative charge by the deslocalization of pi e-(reasonance) ,but the C6H5O- only have one oxygen and 6C for reasonance so the negative charge in CH3CO2- is not readly to donate than in C6H5O- moreover the CH6H5O- have a more carbon than CH3CO2- which have a stronge positive inductive effect . so the C6H5O- is a stronger nucleophilie than CH3CO2-. 希望幫到你拉..

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Nucleophiles(Nu) are proton-loving species and they are protons acceptors( Lewis bases), so stronger Nu means more electron-rich or even -ve particles. C6H5O- is a phenoxide which is a benzene ring attached with an negatively charged O atom, although there is delocalization of pi e- , O is still the most electronegative atom and hence the delocalized pi e- will be strongly distorted towards the O atom, making it even more -ve and a very strong Nu. On the other hand, CH3CO2- is an ethanoate and although there is an negatively charged O atom, the pi e- in COO- group can undergo resonance(delocalization) and the charge can be spread between the two equally electronegative O atoms, making the -ve charge less intense and hence it is a weaker Nu than C6H5O-.