Why acetate ion is more stable than phenoxide ion?

The carboxylate ion is more stable than the phenoxide ion. This is because in the phenoxide ion, the negative charge resides on one electronegative oxygen atom and the lesser electronegative carbon atoms. Consequently their contribution towards resonance stabilisation of the phenoxide ion is less.

Why acetate is stable conjugate base as compared to phenoxide?

In acetate ion -ve charge is distrbuted only on more electronegative two O atoms, while in phenoxide ion , it is 75\% on less electronegative C atoms. So acetate ion is more stable.

Why is acetate ion more stable?

It is due to the delocalization of electrons. Resonance structures induce all oxygens to share the negative charge in acetate equally. As the +I inductive effect of \[{C_2}{H_5}{O^ – }\] makes it unstable, this resonance effect is not possible in ethoxide ions.

Why is acetate ion more stable than acetic acid?

The delocalization of charge by resonance has a very powerful effect on the reactivity of organic molecules, enough to account for the difference of over 12 pKa units between ethanol and acetic acid. The acetate ion is that much more stable than the ethoxide ion, all due to the effects of resonance delocalization.

Why is phenoxide more stable than phenol?

Phenoxide ion is more stable than phenol due to the delocalisation of negative charge in phenoxide ion. Explanation: Due to delocalisation of negative charge, phenoxide ion is more stable than phenol.

Why is phenoxide ion more resonance stabilized than phenol?

Whereas in case of phenoxide ion, the negative charge on the oxygen atom get delocalize and no such charge separation take place. Therefore the resonance structures of phenoxide ion has more contributions toward the hybrid in stabilising the phenoxide ion. Hence phenoxide ion is more stable than phenol.

Why phenoxide ion is stable than phenol?

Why is phenoxide ion more stable than Alkoxide ion?

Stability of an ion depends upon the delocalization of its electrons which is known as ‘resonance’. Now, in this case ‘Phenoxide Ion’ has 5 resonating structures, while resonance is not possible in ‘Alkoxide Ion’. Therefore, Phenoxide Ion is more stable than Alkoxide Ion.

Is the acetate ion stable?

Similarly when compared to the phenoxide ion, the acetate ion is highly stable. The negative charge occupies on one electronegative oxygen atom and the smaller negative carbon atoms in phenoxide ion. Therefore in the resonance stabilization of the phenoxide ion, the contribution of negative charge is less.

Why acetate is stable conjugate base?

Because acetate ion has resonance that delocalizes the electron pair to be shared with a proton and ethoxide ion does not, acetate ion is a weaker base than ethoxide ion.

Why phenoxide ion is more stable than Alkoxide?

Why is phenoxide more nucleophilic than phenol?

Compare the resonance structure of phenol and phenoxide ion: On the other hand there is no positive charge on oxygen in case of phenoxide ion and it is more stabilized than phenol . So it is more nucleophilic than phenol that is why it is more reactive towards electrophilic aromatic substitution.

What is the difference between acetate ion and phenoxide ion?

Both acetate ion and phenoxide ions are resonance stabilised but in case of acetate ion the dispersal of negative charge takes place only on the oxygen whereas in phenoxide ion it occurs on the carbon of the benzene ring which is less stable.we get equivalent resonating structures in case of acetate ion.

Why is carboxylate ion more stable than phenoxide ion?

Phenoxide ion has non- equivalent resonance structures in which the negative charge is less effectivelydelocalised over lesselectronegative carbon atom and one oxygen atom.The carboxylate ion is more stable than the phenoxide ion.

Are the resonating structures of acetate ion identical?

It is seen that the resonating structures of acetate ion are identical. The concept of the stability between resonance structures of different compounds need to be known.

Which is more stable phenol or phenoxide ion?

Phenoxide ion is more stable than phenol, although both phenol and phenoxide have same number of resonating sturcture . In phenoxide ion the negative charge on oxygen atom takes part in resonance with the pi electron of benzene ring , through which phenoxide ion got stability .