Chapter 18.2, Problem 18.2P

Interpretation Introduction

Interpretation:

The dissolution of phthalimide in aqueous sodium bicarbonate has to be determined.

Concept introduction:

Acidity of imides:

Imides have a $\text{pKa}$ range of 8-10 and therefore more acidic than amides. They can be readily dissolve in 5% aqueous sodium hydroxide. The acidity can be indicated by the imide anion’s stabilization by delocalisation of its negative charge.