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 CH3NO2 CH2(NO2)2 CH(NO2)3 pKa = 50 pKa=10.2 pKa= 3.6 pK =0.17

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.38P
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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.

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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
CH3NO2
CH2(NO2)2
CH(NO2)3
pKa = 50
pKa = 10.2
pK = 3.6
pKa = 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 CH3NO2 CH2(NO2)2 CH(NO2)3 pKa = 50 pKa = 10.2 pK = 3.6 pKa = 0.17
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