Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
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Chapter 3, Problem 59IP
Interpretation Introduction

Interpretation:

Constitutional isomers needed to be drawn for the given molecular formula C4H9NO2 and identify the least acidic isomer (higher pka ).

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 has less pka corresponding anion is weak base. And the least stable anion has higher pka value.
  • If more sterically hindered the group, basic nature is more for that molecule. That means bulkiness increases the basic strength of the molecule. 

To draw: the constitutional isomers for the molecular formula C4H9NO2 .

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