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8Appendix Chapter 1 • Keys toC the Study of Chemistry

Equilibrium Constants for Selected Substances*

Dissociation (Ionization) Constants (Ka) of Selected Acids † Name and Formula Lewis Structure Ka1 Ka2 Ka3 H O 2 Acetic acid H C C O H 1.8310 5 CH3COOH H

H H C C O 2 Acetylsalicylic acid H C C C O H 3.6310 4 CH3COOC6H4COOH CC O H H O CCH

H

O H H H H O 2 2 Adipic acid H O C C C C C C O H 3.8310 5 3.8310 6 HOOC(CH2)4COOH H H H H

O 2 2 2 Arsenic acid H O As O H 6310 3 1.1310 7 3310 12 H3AsO4 O H

H O O H C C H 25 212 Ascorbic acid H C C O 1.0310 5310 O H2C6H6O6 O C C H

H H O H

H H C C O 2 Benzoic acid H C C C O H 6.3310 5 C6H5COOH CCC H H

O 2 2 Carbonic acid HHO C O 4.5310 7 4.7310 11 H2CO3 H O 2 Chloroacetic acid Cl C C O H 1.4310 3 ClCH2COOH H

2 Chlorous acid H O Cl O 1.1310 2 HClO2 *All values at 298 K, except for acetylsalicylic acid, which is at 37ºC (310 K) in 0.15 M NaCl. (continued) †Acidic (ionizable) proton(s) shown in red. Structures have lowest formal charges. Benzene rings show one resonance form.

A-8

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Dissociation (Ionization) Constants (Ka) of Selected Acids † Name and Formula Lewis Structure Ka1 Ka2 Ka3 H

O H O H O 2 2 2 Equilibrium Constants for Selected Substances* Citric acid H O C C C C C O H 7.4310 4 1.7310 5 4.0310 7 HOOCCH2C(OH)(COOH)CH2COOH H H C O

O H

O 2 Formic acid HCO H 1.8310 4 HCOOH

H H O 2 Glyceric acid H O C C C O H 2.9310 4 HOCH2CH(OH)COOH H O H

H O 2 Glycolic acid H O C C O H 1.5310 4 HOCH2COOH H

H O 2 Glyoxylic acid O C C O H 3.5 310 4 HC(O)COOH 2 Hydrocyanic acid H C N 6.2310 10 HCN

2 Hydrofluoric acid H F 6.8310 4 HF 2 2 Hydrosulfuric acid H S H 9310 8 1310 17 H2S 2 H O Br 2.3310 9 HBrO

2 H O Cl 2.9310 8 HClO

2 H O I 2.3310 11 HIO

O 2 Iodic acid H O I O 1.6310 1 HIO3 H H O 2 Lactic acid H C C C O H 1.4310 4 CH3CH(OH)COOH H O H

H H C C 2 2 Maleic acid O C C O 1.2310 2 4.7310 7 HOOCCH CHCOOH H O O H

(continued)

siL02656_apA-D_A-1_A-14.indd 9 12/9/10 8:28:18 AM A-10 Appendix C • Equilibrium Constants for Selected Substances

Dissociation (Ionization) Constants (Ka) of Selected Acids (continued ) † Name and Formula Lewis Structure Ka1 Ka2 Ka3 O H O 2 2 Malonic acid H O C C C O H 1.4310 3 2.0310 6 HOOCCH2COOH H

2 Nitrous acid H O N O 7.1310 4 HNO2 O O 2 2 Oxalic acid H O C C O H 5.6310 2 5.4310 5 HOOCCOOH H H C C 2 Phenol H C C O H 1.0310 10 C6H5OH CCC H H

H H C C H O 2 Phenylacetic acid H C C C C O H 4.9310 5 C6H5CH2COOH CCC H HH

O 2 2 2 Phosphoric acid H O P O H 7.2310 3 6.3310 8 4.2310 13 H3PO4 O H

O 2 2 Phosphorous acid H P O H 3310 2 1.7310 7 HPO(OH)2 O H

H H O 2 Propanoic acid H C C C O H 1.3310 5 CH3CH2COOH H H

H O O 2 Pyruvic acid H C C C O H 2.8310 3 CH3C(O)COOH H

O H H O 2 2 Succinic acid H O C C C C O H 6.2310 5 2.3310 6 HOOCCH2CH2COOH H H

O 2 H O S O H Very large 1.0310 2 H2SO4 O

O 2 2 Sulfurous acid H O S O H 1.4310 2 6.5310 8 H2SO3 (continued)

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Dissociation (Ionization) Constants (Kb) of Selected Amine Bases † Name and Formula Lewis Structure Kb1 Kb2

2 Ammonia H N H 1.76310 5 NH3 H

H H C C 2 Aniline H C C N H 4.0310 10 C6H5NH2 CCC H H H

H H H H 2 Diethylamine HHC C N C C 8.6310 4 (CH3CH2)2NH H H H H H

H H 2 Dimethylamine H C N C H 5.9310 4 (CH3)2NH H H H

H H 2 Ethanolamine H O C C N H 3.2310 5 HOCH2CH2NH2 H H H

H H 2 Ethylamine H C C N H 4.3310 4 CH3CH2NH2 H H H

H H 2 2 Ethylenediamine H N C C N H 8.5310 5 7.1310 8 H2NCH2CH2NH2 H H HH

H 2 Methylamine H C N H 4.4310 4 CH3NH2 HH

H H N H H 2 tert-Butylamine H CCC H 4.8310 4 (CH3)3CNH2 H HHC H

H

HH H H H C C 2 Piperidine C N H 1.3310 3 C5H10NH H C C H H HH

H H H 2 n-Propylamine H C C C N H 3.5310 4 CH3CH2CH2NH2 H H H H

†Blue type indicates the basic nitrogen and its lone pair. (continued )

siL02656_apA-D_A-1_A-14.indd 11 12/9/10 8:28:19 AM A-12 Appendix C • Equilibrium Constants for Selected Substances

Dissociation (Ionization) Constants (Kb) of Selected Amine Bases (continued )

† Name and Formula Lewis Structure Kb1 Kb2

H H N H H 2 Isopropylamine H CCC H 4.7310 4 (CH3)2CHNH2 H H H

H H H 2 2 1,3-Propylenediamine H N C C C N H 3.1310 4 3.0310 6 H2NCH2CH2CH2NH2 H H H H H

H H C C 2 Pyridine H C N 1.7310 9 C5H5N CCC H H

H H H H 2 Triethylamine H C C N C C H 5.2310 4 (CH3CH2)3N H H HHC H H

HHC H

H H 2 Trimethylamine H C N C H 6.3310 5 (CH3)3N H HHC H

H

Dissociation (Ionization) Constants Formation Constants (Kf) (Ka) of Some Hydrated Metal Ions of Some Complex Ions

Free Complex Ion Kf Ion Hydrated Ion Ka 2 20 Ag(CN)2 3.0310 31 31 23 1 3 7 Fe Fe(H2O)6 (aq) 6310 Ag(NH3)2 1.7 10 21 21 24 32 3 13 Sn Sn(H2O)6 (aq) 4310 Ag(S2O3)2 4.7 10 31 31 24 32 3 19 Cr Cr(H2O)6 (aq) 1310 AlF6 4 10 31 31 25 2 3 33 Al Al(H2O)6 (aq) 1310 Al(OH)4 3 10 21 21 28 22 3 18 Cu Cu(H2O)6 (aq) 3310 Be(OH)4 4 10 21 21 28 22 3 6 Pb Pb(H2O)6 (aq) 3310 CdI4 1 10 21 21 29 22 3 9 Zn Zn(H2O)6 (aq) 1310 Co(OH)4 5 10 21 21 210 2 3 29 Co Co(H2O)6 (aq) 2310 Cr(OH)4 8.0 10 21 21 210 21 3 11 Ni Ni(H2O)6 (aq) 1310 Cu(NH3)4 5.6 10 42 35 Fe(CN)6 3 310 32 43 Fe(CN)6 4.0310 22 38 Hg(CN)4 9.3310 21 8 Ni(NH3)6 2.0310 2 13 Pb(OH)3 8 310 2 25 Sn(OH)3 3 310 22 19 Zn(CN)4 4.2310 21 8 Zn(NH3)4 7.8310 22 15 Zn(OH)4 3 310

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Solubility-Product Constants (Ksp) of Slightly Soluble Ionic Compounds

Name, Formula Ksp Name, Formula Ksp

215 Carbonates Cobalt(II) , Co(OH)2 1.3310 29 220 Barium carbonate, BaCO3 2.0310 Copper(II) hydroxide, Cu(OH)2 2.2310 214 215 carbonate, CdCO3 1.8310 Iron(II) hydroxide, Fe(OH)2 4.1310 29 239 Calcium carbonate, CaCO3 3.3310 Iron(III) hydroxide, Fe(OH)3 1.6310 210 210 Cobalt(II) carbonate, CoCO3 1.0310 , Mg(OH)2 6.3310 212 213 Copper(II) carbonate, CuCO3 3.0310 Manganese(II) hydroxide, Mn(OH)2 1.6310 214 216 Lead(II) carbonate, PbCO3 7.4310 Nickel(II) hydroxide, Ni(OH)2 6.0310 28 216 Magnesium carbonate, MgCO3 3.5310 , Zn(OH)2 3.0310 217 Mercury(I) carbonate, Hg2CO3 8.9310 Iodates 27 29 Nickel(II) carbonate, NiCO3 1.3310 Barium iodate, Ba(IO3)2 1.5310 210 27 Strontium carbonate, SrCO3 5.4310 Calcium iodate, Ca(IO3)2 7.1310 210 213 Zinc carbonate, ZnCO3 1.0310 Lead(II) iodate, Pb(IO3)2 2.5310 28 Chromates Silver iodate, AgIO3 3.1310 210 27 Barium chromate, BaCrO4 2.1310 Strontium iodate, Sr(IO3)2 3.3310 28 26 Calcium chromate, CaCrO4 1.0310 Zinc iodate, Zn(IO3)2 3.9310 213 Lead(II) chromate, PbCrO4 2.3310 Oxalates 212 27 Silver chromate, Ag2CrO4 2.6310 Barium oxalate dihydrate, BaC2O42H2O 1.1310 29 Cyanides Calcium oxalate monohydrate, CaC2O4H2O 2.3310 240 Mercury(I) cyanide, Hg2(CN)2 5.0310 Strontium oxalate monohydrate, 216 28 Silver cyanide, AgCN 2.2310 SrC2O4H2O 5.6310 Halides Phosphates 229 Fluorides Calcium phosphate, Ca3(PO4)2 1.2310 26 224 Barium fluoride, BaF2 1.5310 Magnesium phosphate, Mg3(PO4)2 5.2310 211 218 Calcium fluoride, CaF2 3.2310 Silver phosphate, Ag3PO4 2.6310 28 Lead(II) fluoride, PbF2 3.6310 Sulfates 29 210 Magnesium fluoride, MgF2 7.4310 Barium sulfate, BaSO4 1.1310 29 25 Strontium fluoride, SrF2 2.6310 Calcium sulfate, CaSO4 2.4310 28 Chlorides Lead(II) sulfate, PbSO4 1.6310 27 211 Copper(I) chloride, CuCl 1.9310 Radium sulfate, RaSO4 2.0310 25 25 Lead(II) chloride, PbCl2 1.7310 Silver sulfate, Ag2SO4 1.5310 210 27 Silver chloride, AgCl 1.8310 Strontium sulfate, SrSO4 3.2310 Bromides Sulfides 2 2 Copper(I) bromide, CuBr 5 310 9 , CdS 1.0310 24 2 2 Silver bromide, AgBr 5.0310 13 Copper(II) sulfide, CuS 8.0310 34 2 Iodides Iron(II) sulfide, FeS 8.0310 16 2 2 Copper(I) iodide, CuI 1 310 12 Lead(II) sulfide, PbS 3.0310 25 29 211 Lead(II) iodide, PbI2 7.9310 Manganese(II) sulfide, MnS 3.0310 229 250 Mercury(I) iodide, Hg2I2 4.7310 Mercury(II) sulfide, HgS 2.0310 2 2 Silver iodide, AgI 8.3310 17 Nickel(II) sulfide, NiS 3.0310 16 248 Silver sulfide, Ag2S 8.0310 234 223 Aluminum hydroxide, Al(OH)3 3 310 Tin(II) sulfide, SnS 1.3310 215 222 Cadmium hydroxide, Cd(OH)2 7.2310 Zinc sulfide, ZnS 2.0310 26 , Ca(OH)2 6.5310

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