Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
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Chapter 3, Problem 57IP
Interpretation Introduction

Interpretation:

More acidic nature of salicylic acid than its constitutional isomers is needed to be explained.

Concept introduction:

Constitutional isomers:

  • Constitutional isomers are isomers which have the same molecular formula and different bond connectivity between the atoms in the molecule.

Acidic strength of the molecule depends on the stability of the Conjugate anion.

  • If the conjugate anion is more resonance stabilized, the acid considered as strong acid and the anion is weak base.
  • If more sterically hindered the group, acidic nature is less. That means bulkiness decreases the acidic strength of the molecule. 

To give: the explanation for the acidity of salicylic acid than para-hydroxybenzoic acid.

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