Answer.
Ortho and para nitrophenols are more acidic than phenol. Resonance exists only when a Lewis structure has multiple bonds and an adjacent atom with at least one lone pair. Draw three resonance structures of phenol. Answer : Resonance structure : It is defined as when more than one Lewis structure can be drawn, the molecule or ion is said to have resonance.

Draw the resonance structures of the corresponding phenoxide ions.

Resonating structures of phenoxide ions that are formed by the loss of a proton from phenol are as follows: It is clearly evident from the above structures that due to —R-effect of— NO 2 NO 2 group, o-and p-nitrophenoxide ions are more stable than phenoxide ions.


They undergoes resonance to attain stability. a. Phenolate ion, phenol's conjugate base, being stable by this resonance, is a weak base, so phenol becomes acidic. Phenol (shown below) has a p K a ≈ 10 . The existence of this resonance in phenolate ion provides it quite some stability, hence phenol is acidic. Resonance structures of p-nitrophenoxide ion.

Explain why the second-order resonance contributors are less important than first-order resonance structures, and contribute only a small amount to our overall understanding of phenol. Is the OH group a donor or acceptor? Resonance is the concept where electrons (bonds) are delocalized over three or more atoms which cannot be depicted with one simple Lewis structure.

Is phenol activated towards electrophilic aromatic substitution or deactivated? Below is an example of a resonance structure that would break the octet rule, so it is a resonance structure that cannot be drawn. b. The first step of drawing resonance structures starts with drawing all the possible Lewis structures. Phenol are the aromatic compound have hydroxyl group attached to aromatic hydrocarbon.

The pKa of the 4-methylumbelliferone is 2-3 units lower than the pKa of phenol.

When drawing resonance structures, you must be sure to never exceed the octet rule for elements that follow this rule (C, N, O, F, Cl, Br, I).

c. Construct an explanation for why phenol is a stronger acid than anordinary alcohol. a.

If it has only one Lewis structure, it doesn’t have a resonance hybrid. Nucleophilic substitution reactions of phenols are generally carried out under basic conditions as the phenolate ion is a better nucleophile.

In these resonating structures, positive and negative charges are present together. Consequently, o- and p-nitrophenols are more acidic than phenols.

There are four resonating structures of phenol. Based on p K a data, is phenol a stronger or weaker acid than an ordinaryalcohol (e.g.. CH 3 OH ) or water? How to Identify the Molecules Having Resonance. The acidity of nitrophenols (or any acid for that matter) is determined by the stability of the conjugate base. Draw three second-order resonance structures for phenol. Resonance structures of o-nitrophenoxide ion. Well the following resonance structures are of the phenolate ion, which are correct.