Why C6H5O- is a stronger nucleophile than CH3CO2-?

2008-09-15 11:49 pm
Why C6H5O- is a stronger nucleophile than CH3CO2-?

回答 (2)

2008-09-16 7:02 am
✔ 最佳答案
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-.

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參考: myself
2008-09-18 2:49 am
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-.
參考: Chem knowledge


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