Answered: Rank the following compounds in order…

Rank the following compounds in order of increasing pKa: (A) para-chlorobenzoic acid (B) meta-chlorobenzoic acid (C) ortho-chlorobenzoic acid (D) benzoic acid a. D, A, B, C

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 37AP

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Concept explainers

Organomagnesium compounds

The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.

Hydrolysis Grignard Reactions and Reduction

Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.

Question

Rank the following compounds in order of increasing pKa:

(A) para-chlorobenzoic acid

(B) meta-chlorobenzoic acid

(D) benzoic acid

a. D, A, B, C

b. D, A, C, B

c. D, C, B, A

d. A, B, C, D

e. C, B, A, D

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