The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why ?
The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why ?
(i)In phenol, the conjugation of unshared electron pairs over oxygen with aromatic ring results in partial double bond character in C – O bond.
In methanol, no such conjugation (resonance) is possible.
(ii) In phenol, oxygen is attached to sp2 hybridised carbon while in methanol, oxygen attached to sp3 hybridised carbon. An sp2 hybridised carbon is more electronegative (because of greater 5-character) than the sp3 hybridised carbon atom. Therefore, the bond between oxygen and sp2 hybridised carbon is more stable than the bond between oxygen and sp3 hybridised orbital.
From the above resonating structure, it is very clear that C - O bond of phenol acquires some partial double bond character while the C - O bond of methanol is purely single bond
Therefore, the carbon-oxygen bond in phenol is slightly stronger than that in methanol.
(i)In phenol, the conjugation of unshared electron pairs over oxygen with aromatic ring results in partial double bond character in C – O bond.
In methanol, no such conjugation (resonance) is possible.
(ii) In phenol, oxygen is attached to sp2 hybridised carbon while in methanol, oxygen attached to sp3 hybridised carbon. An sp2 hybridised carbon is more electronegative (because of greater 5-character) than the sp3 hybridised carbon atom. Therefore, the bond between oxygen and sp2 hybridised carbon is more stable than the bond between oxygen and sp3 hybridised orbital.
From the above resonating structure, it is very clear that C - O bond of phenol acquires some partial double bond character while the C - O bond of methanol is purely single bond
Therefore, the carbon-oxygen bond in phenol is slightly stronger than that in methanol.
