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Question:Phenols generally have lower pKa’s than aliphatic alcohols because of resonance stabilization with the aromatic ring. Draw all of the resonance contributors for the phenolate ions below. Make note of how the substituents either stabilize or destabilize the system.

Short Answer

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a.

b.

c.

Step by step solution

01

Resonating structure

The structures are produce by the delocalisation of the pi electrons and the structure are called the Lewis acid.

02

Resonating structure of Phenoxide a

Phenoxide are formed by the phenol by abstraction of hydroxyl proton and they are more acidic in nature and have low pKa value and show resonance as oxygen having negative charge as shown below and here, the last resonating structure destabilize the molecule due to negative charge at para with alkyl group.

Resonating structure of Phenoxide A

03

Resonating structure of Phenoxide b

Phenoxide are formed by the phenol by abstraction of hydroxyl proton and they are more acidic in nature and have low pKa value and show resonance as oxygen having negative charge as shown below:

Resonating structure of Phenoxide b

04

Resonating structure of Phenoxide C

Phenoxides are formed by the phenol by abstraction of hydroxyl proton and they are more acidic in nature and have low pKa value and show resonance as oxygen having negative charge as shown below here, the third structure is stabilize because of oxygen atom present having lone pair which also take part in delocalisation and make the system more stable:

Resonating structure of Phenoxide C

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