phenols

Y phenoxide is more reactive towards electophilic substitution than phenols

11 Answers

62
Lokesh Verma ·

There is delocalisation of electrons in both phenol and phenoxide ion.

But in phenol there is a charge seperation ... ie + and - are created from a neutral molecule

But in Phenoxide, there is only a -ve charge and there is no charge seperation

62
Lokesh Verma ·

you should also note that number of resonance structure is the same in both....

24
eureka123 ·

how is this possible???????[11][11][11][1]

Nishant sir in ORganic section and actually answering the doubts.........[3]

1
voldy ·

come on eureka he's done 4 yreas more study than what we've done in chemistry. I dunno why manish and nishant don't reply here often

24
eureka123 ·

yup u r correct............I only see him in math and physics sections...........

1
voldy ·

and he'll say I've not asnwered much in phy and math :) which is very true

62
Lokesh Verma ·

haha.. I am not good at chem man..

I have forgotten all that i knew then...

Now it is pretty much guess work + instinct :)

which gagar kill me when i post wrong answers ;)

so i avoid doing anything wrong.. but preeti was not getting the answers so i thought may be i could try to help with the little knowledge that i have

39
Dr.House ·

phenoxide has single charge delocalisation and highlyyy effective resonance.

1
vector ·

o- shows more +m effect than oh

1
rohan poddar ·

well as rightly pointed out earlier... phenoxide has a single charge delocalisation due to which there is only -ve charge residing in the compound..

On the other hand we find that in phenol there is charge separation.
causing the compund to have both +ve and -ve charges..

It shuld be remembered that presence of +ve or -ve charges in a compound causes vibration in the compound making it unstable and thus less prone to electophilic attack..

As phenoxide ion is more stable it is highly reactive towards electrophilic attack....

I think this myt clear all doubts ...

this is also the reason as to y all reactions of phenols actually commences from the phenoxide ion.

1
voldy ·

and @ Nishant . I always go by my instinct . actually most problems are solved by this only . basic is check fo r nucleophile electrophile , that's all then everything happens on it's own .organic is like math , a bit.

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