The structural formulas of pseudoephedrine (a free base) and pseudoephedrine hydrochloride (a quaternary ammonium compound) are shown below. Which of these two compounds would you predict to be more water-soluble? Can you explain to me and help me, please?

The structural formulas of pseudoephedrine (a free base) and pseudoephedrine hydrochloride (a quaternary ammonium compound) are shown below. Which of these two compounds would you predict to be more water-soluble? Can you explain to me and help me, please?

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter19: Carboxylic Anhydrides, Esters, And Amides

Section: Chapter Questions

Problem 19.44P

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Can you explain to me and help me, please?

9.30) The structural formulas of pseudoephedrine (a free base) and pseudoephedríne hydrochloride (a quaternary ammoníum
compound) are shown below. Which of these two compounds would you predict to be more water-soluble?
lo
pseudoephedrine hydrochloride
CH3
-CHCHNHCH3
OH
pseudoephedrine
CH3
| +
-CHCHNH₂CH3 CI
OH
more water-soluble

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