×
Log in to StudySoup
Get Full Access to Organic Chemistry - 7 Edition - Chapter 2.7 - Problem 31
Join StudySoup for FREE
Get Full Access to Organic Chemistry - 7 Edition - Chapter 2.7 - Problem 31

Already have an account? Login here
×
Reset your password

If HCl is a weaker acid than HBr, why is ClCH 2 COOH a stronger acid than BrCH 2 COOH

Organic Chemistry | 7th Edition | ISBN: 9780321803221 | Authors: Paula Yurkanis Bruice ISBN: 9780321803221 462

Solution for problem 31 Chapter 2.7

Organic Chemistry | 7th Edition

  • Textbook Solutions
  • 2901 Step-by-step solutions solved by professors and subject experts
  • Get 24/7 help from StudySoup virtual teaching assistants
Organic Chemistry | 7th Edition | ISBN: 9780321803221 | Authors: Paula Yurkanis Bruice

Organic Chemistry | 7th Edition

4 5 1 265 Reviews
24
4
Problem 31

If HCl is a weaker acid than HBr, why is ClCH 2 COOH a stronger acid than BrCH 2 COOH? Solution To compare the acidities of HCl and HBr, we need to compare the stabilities of their conjugate bases, Cl- and Br - . (Notice that an HCl bond breaks in one compound and an HBr bond breaks in the other.) Because we know that size is more important than electronegativity in determining stability, we know that Br - is more stable than Cl- . Therefore, HBr is a stronger acid than HCl. In comparing the acidities of the two carboxylic acids, we again need to compare the stabilities of their conjugate bases, ClCH 2 COO - and BrCH 2 COO - . (Notice that an OiH bond breaks in both compounds.) The only way the conjugate bases differ is in the electronegativity of the atom that is drawing electrons away from the negatively charged oxygen. Because Cl is more electronegative than Br, Cl exerts greater inductive electron withdrawal. Thus, it has a greater stabilizing effect on the base that is formed when the proton leaves, so the chlorosubstituted compound is the stronger acid.

Step-by-Step Solution:
Step 1 of 3

Alyssa Nielsen Linda Pollock Living with Feelings (Honors) 12 September 2016 What Is an Emotion The term “emotion” is a relatively new appellation that covers a broad scope of mental states within modern day psychological and social thought. Thomas Dixon examines this word and what it has come to mean in his book From Passions to Emotions, shining a light on the evolution of previously...

Step 2 of 3

Chapter 2.7, Problem 31 is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 7
Author: Paula Yurkanis Bruice
ISBN: 9780321803221

Other solutions

People also purchased

Related chapters

Unlock Textbook Solution

Enter your email below to unlock your verified solution to:

If HCl is a weaker acid than HBr, why is ClCH 2 COOH a stronger acid than BrCH 2 COOH