Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 47AP
Interpretation Introduction
Interpretation:
Whether tert-butoxide ion is a base, strong enough to react significantly with water or can a solution of ter-butoxide prepared in water is to be decided. pKa of tert-butyl alcohol is given as approximately 18.
Concept introduction:
Water can act as an acid or as a base. It can donate H+ to substances which are weaker acids (with higher pKa value than that of water) than water. It can accept H+ from substances which are stronger acids (with lower pKa value than that of water).
To determine:
Whether tert-butoxide ion is a base, strong enough to react significantly with water or can a solution of ter-butoxide prepared in water. pKa of tert-butyl alcohol is given as approximately 18.
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Use the four compounds shown below to answer the following questions:
a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?
Use the four compounds shown below to answer the following questions:
a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid? b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids? c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?
which acid of each pair would you expect to be stronger?
based on your answer, provide a reaction of the selected stronger acid forming a carboxylate ion
#1
Chapter 2 Solutions
Organic Chemistry
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