Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of the compounds, and explain why the acidity increases so dramatically with substitution by nitro groups. CH4 CH;NO2 CH2(NO2)2 CH(NO2)3 pK = 50 pK = 10.2 pKa = 3.6 pKa =0.17

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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draw the conjugate base

Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these
compounds, and explain why the acidity increases so dramatically with substitution by nitro groups.
CH4
CH;NO2
CH2(NO2)2
CH(NO2)3
pK, = 50
pKa = 10.2
pK = 3.6
pK =0.17
Transcribed Image Text:Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups. CH4 CH;NO2 CH2(NO2)2 CH(NO2)3 pK, = 50 pKa = 10.2 pK = 3.6 pK =0.17
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