The existence of this resonance in phenolate ion provides it quite some stability, hence phenol is acidic. Phenolate ion, phenol's conjugate base, being stable by this resonance, is a weak base, so phenol becomes acidic. c. Construct an explanation for why phenol is a stronger acid than anordinary alcohol. The first step of drawing resonance structures starts with drawing all the possible Lewis structures. How to Identify the Molecules Having Resonance. Is phenol activated towards electrophilic aromatic substitution or deactivated? b. Ortho and para nitrophenols are more acidic than phenol. Consequently, o- and p-nitrophenols are more acidic than phenols. They undergoes resonance to attain stability. Draw three second-order resonance structures for phenol. a. There are four resonating structures of phenol. Resonance is the concept where electrons (bonds) are delocalized over three or more atoms which cannot be depicted with one simple Lewis structure. Draw the resonance structures of the corresponding phenoxide ions. 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. Resonance structure of the phenoxide ion. Draw the conjugate base of phenol (called phenoxide) including allimportant resonance structures.

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? In these resonating structures, positive and negative charges are present together. The acidity of nitrophenols (or any acid for that matter) is determined by the stability of the conjugate base. Draw three resonance structures of phenol. Phenol (shown below) has a p K a ≈ 10 . Resonance exists only when a Lewis structure has multiple bonds and an adjacent atom with at least one lone pair. Nucleophilic substitution reactions of phenols are generally carried out under basic conditions as the phenolate ion is a better nucleophile. The pKa of the 4-methylumbelliferone is 2-3 units lower than the pKa of phenol. Resonance structures of o-nitrophenoxide ion. Based on p K a data, is phenol a stronger or weaker acid than an ordinaryalcohol (e.g.. CH 3 OH ) or water? 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. Answer. Below is an example of a resonance structure that would break the octet rule, so it is a resonance structure that cannot be drawn. a. 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). If it has only one Lewis structure, it doesn’t have a resonance hybrid. Phenol are the aromatic compound have hydroxyl group attached to aromatic hydrocarbon. Well the following resonance structures are of the phenolate ion, which are correct.