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Mcmurry

This document lists the pKa values for various organic compounds. It provides the compound name and pKa for over 50 compounds. It notes that an extensive list of pKa values for over 5000 organic compounds has been published in a reference text.

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vinicius oliveira
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287 views2 pages

Mcmurry

This document lists the pKa values for various organic compounds. It provides the compound name and pKa for over 50 compounds. It notes that an extensive list of pKa values for over 5000 organic compounds has been published in a reference text.

Uploaded by

vinicius oliveira
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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| APPENDIXB

Acidity Constants for Some Organic Compounds


Compound
CH3SO3H CH(NO2)3 NO2 O2N OH NO2 CCl3CO2H CF3CO2H CBr3CO2H HO2CCqCCO2H HO2CCO2H CHCl2CO2H CH2(NO2)CO2H HCqCCO2H (Z) HO2CCHPCHCO2H CO2H

pKa
21.8 0.1

Compound
CO2H

pKa
3.0

Compound
CH2BrCH2CO2H O2N NO2

pKa
4.0

Cl CO2H OH

4.1

0.3
OH CH2ICO2H

3.0

CO2H

4.2 3.2 3.2


CO2H H2CPCHCO2H HO2CCH2CH2CO2H

0.5 0.5 0.7 1.2; 2.5 1.2; 3.7 1.3 1.3 1.9 1.9; 6.3

CHOCO2H O2N O2N O2N HSCH2CO2H CH2(NO2)2 CH3OCH2CO2H CO2H

4.2 4.2; 5.7 4.3; 5.4

3.4

HO2CCH2CH2CH2CO2H Cl Cl OH Cl Cl

3.5

Cl

4.5

3.5; 10.2 3.6 3.6 3.6 3.7 3.7

H2CPC(CH3)CO2H CH3CO2H CH3CH2CO2H (CH3)3CCO2H CH3COCH2NO2 O

4.7 4.8 4.8 5.0 5.1

2.4
NO2 CH3COCO2H NCCH2CO2H CH3CqCCO2H CH2FCO2H CH2ClCO2H HO2CCH2CO2H CH2BrCO2H

CH3COCH2CO2H HOCH2CO2H

2.4 2.5 2.6 2.7 2.8 2.8; 5.6 2.9

HCO2H Cl CO2H

3.8
O

5.3

Cl

CO2H

4.0

O2NCH2CO2CH3

5.8

A-8
C opyright 2010 C engage L earning. A ll R ights R eserved. M ay not be copied, scanned, or duplicated, in whole or in part. D ue to electronic rights, some third party content may be suppressed from the eB ook and/or eC hapter(s). E ditorial review has deemed that any suppressed content does not materially affect the overall learning experience. C engage L earning reserves the right to remove additional content at any time if subsequent rights restrictions require it.

APPENDIXB | AcidityConstantsforSomeOrganicCompounds

A-9

Compound
O

pKa

Compound
CH2SH

pKa
9.4

Compound
H2CPCHCH2OH CH3CH2OH CH3CH2CH2OH

pKa
15.5 16.0 16.1 16.1 16.7 17 17 17.1 18.0 19.3 23

5.8
CHO Cl Cl Cl SH HCO3H NO2 OH OH

CH3COCH2Br

9.9; 11.5 6.2


HO OH CH3CHO (CH3)2CHCHO O

9.9 6.6 7.1


CH3COCH2SOCH3 OH

10.0

(CH3)2CHOH (CH3)3COH

10.3
CH3 CH3NO2

CH3COCH3

7.2
OH (CH3)2CHNO2 Cl Cl CH3CO3H OH OH CH3SH

10.3 10.3 10.6 11.0 11.2 12.2 12.3 12.4 12.9 12.9 13.3 14.1 14.3 15.0
CH3CO2CH2CH3 HCqCH CH3CN CH3SO2CH3 (C6H5)3CH (C6H5)2CH2 CH3SOCH3 NH3 CH3CH2NH2 (CH3CH2)2NH CH3

7.7

25 25 25 28 32 34 35 36 36 40

CH3COCH2CO2CH3

7.8

CH3COCHO CH2(CN)2 CCl3CH2OH

8.2

Glucose (CH3)2CPNOH

8.5
Cl CH3CH2NO2 F3C OH

CH2(CO2CH3)2 CHCl2CH2OH

8.5 8.7 9.0 9.3; 11.1

CH2(OH)2 HOCH2CH(OH)CH2OH CH2ClCH2OH

41

CH3COCH2COCH3 HO OH

43
CH2OH

15.4
H2CPCH2

OH

44 60

9.3; 12.6
OH

CH3OH

15.5

CH4

An acidity list covering more than 5000 organic compounds has been published: E.P. Serjeant and B. Dempsey (eds.), Ionization Constants of Organic Acids in Aqueous Solution, IUPAC Chemical Data Series No. 23, Pergamon Press, Oxford, 1979.

C opyright 2010 C engage L earning. A ll R ights R eserved. M ay not be copied, scanned, or duplicated, in whole or in part. D ue to electronic rights, some third party content may be suppressed from the eB ook and/or eC hapter(s). E ditorial review has deemed that any suppressed content does not materially affect the overall learning experience. C engage L earning reserves the right to remove additional content at any time if subsequent rights restrictions require it.

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