It is an isomer of fumaric acid. Maleic acid, being electrophilic, participates as a dienophile in many Diels-Alder reactions. Maleic acid is a weak diprotic acid with : pK a1 = 1.87 pK a2 = 6.07 A 10.00 mL solution of 0.1000 M maleic acid is titrated with 0.1000 M NaOH. Those values in brackets are considered less reliable. =10.00 mL, The pH of the solution at the first equivalence point. 0000022537 00000 n
No of moles of H2A = 0.01 L 0.1 mol/L = 0.001 mol Additionally, per the publisher's request, their name has been removed in some passages. It is a weak Bronsted acid. Some bacteria produce the enzyme maleate isomerase, which is used by bacteria in nicotinate metabolism. o? 0.1000 M NaOH. "Experimental" often implies to students "untested" or "unreliable", but here it means that someone has done the work to measure how tightly the proton is bound. Figure AB9.2. However, conversion of the cis isomer into the trans isomer is possible by photolysis in the presence of a small amount of bromine. Calculate the pH at the second equivalence point? The Bronsted base does not easily form a bond to the proton. pKa1 = 2.98; pKa2 = 4.34; pKa3 = 5.40: pH: . NaOH- $ values (the bigger the difference, the lower the percentage of $\ce{NaHA}$ undergoing acid or base reactions). Chemical formulas or structural formulas are shown for the fully protonated weak acid. The relationship between pKa and Ka is described by the following equation: pKa = -log [Ka] Acid dissociation constants, or pKa values, are essential for understanding many fundamental reactions in chemistry. 0
In the present study, PMA is explored as an . 0000019496 00000 n
Ka1 and Ka2 are for polyprotic acids and refer to the first deprotonation and second deprotonation reactions. Maleic acid is a weak diprotic acid with : pKa1 = 1.87 pKa2 = 6.07 A 10.00 mL solution of 0.1000 M maleic acid is titrated with 0.1000 M NaOH. Maleic acid is more soluble in water than fumaric acid. Its chemical formula is HO2CCH=CHCO2H. Again, the large difference in water solubility makes fumaric acid purification easy. GD H $ DJ R L d H B s4 3 | s4 s4 s4 H 81 81 I ; ; ; s4 R 81 B 81 m? { "E1:_Acid_Dissociation_Constants_at_25C" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.
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A strong Bronsted acid is a compound that gives up its proton very easily. endstream
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3)Calculate the total volume of NaOH required to . Water does not give up a proton very easily; it has a pKa of 15.7. Malonic acid, H2C3H2O4, is a weak diprotic acid (pKa1 = 2.82 and pKa2 = 5.71 at 25 degrees Celsius). H2A + 2 NaOH Na2A + 2 H2O Legal. pKa1 and pKa2 are the negative logs of the acidity constants for the first and second stage in which a polyprotic acid loses a proton. For example, nitric acid and hydrochloric acid both give up their protons very easily. 1 mol of H2A reacts with 2 mol. When a compound gives up a proton, it retains the electron pair that it formerly shared with the proton. 2)Calculate the pH of the solution at the first equivalence point. The volume of NaOH required to reach the first equivalence However, the terms "strong" and "weak" are really relative. endstream
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What intermolecular forces are present in malonic acid? There is an experimentally-determined parameter that tells us how tightly protons are bound to different compounds. 6.07. Volume NaOH = 0.002000 moles / 0.. Nitric acid in water has a pKa of -1.3 and hydrobromic acid has a pKa of -9.0. This book is licensed under a Creative Commons by-nc-sa 3.0 license. [6], Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.[7]. There's only one value above pKa2 (answer E) so that would be my guess. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. second equivalence. Conjugate bases of strong acids are ineffective bases. Maleic acid is a weak diprotic acid with : 0000000751 00000 n
This problem has been solved! 0000006099 00000 n
point. Legal. It becomes a conjugate base. The following table provides pKa and Ka values for selected weak acids. cis - double bond configuration. Experts are tested by Chegg as specialists in their subject area. Explain how to determine pKa1, pKa2, and the molecular weight. It is helpful to have a way of comparing Bronsted-Lowry acidities of different compounds. In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane. On the other hand, acetic acid (found in vinegar) and formic acid (the irritant in ant and bee stings) will also give up protons, but hold them a little more tightly. Plenum Press: New York, 1976. Maleic acid is a weak diprotic acid with : pKa1 = 1.87 pKa2 = pKa2 = 6.07 For example, the pKa of acetic acid is 4.8, while the pKa of lactic acid is 3.8. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. 0000010457 00000 n
Hydronium ion H3O+ H2O 1 0.0 Unless otherwise stated, values are for 25 oC and zero ionic strength. Moles maleic acid = 0.01000 lit x 0.1000 Mol/lit = 0.001000 xb```b``yXacC;P?H3015\+pc A pKa may be a small, negative number, such as -3 or -5. Methane is not really an acid at all, and it has an estimated pKa of about 50. Appendix C: Dissociation Constants and pKa Values for Acids at 25C Table of Contents Next Section Chapter 27 Appendix C: Dissociation Constants and p Ka Values for Acids at 25C Source of data: CRC Handbook of Chemistry and Physics, 84th Edition (2004). You'll get a detailed solution from a subject matter expert that helps you learn core concepts. o? 0.1000 M NaOH. these intramolecular hydrogen bonds make it difficult to release hydrogen to act as an acid. 0000003442 00000 n
A 10.00 mL solution of 0.1000 M maleic acid is titrated with ), How to make a New Post (submit a question) and use Equation Editor (click for details), How to Subscribe to a Forum, Subscribe to a Topic, and Bookmark a Topic (click for details), Multimedia Attachments (click for details), Accuracy, Precision, Mole, Other Definitions, Bohr Frequency Condition, H-Atom , Atomic Spectroscopy, Heisenberg Indeterminacy (Uncertainty) Equation, Wave Functions and s-, p-, d-, f- Orbitals, Electron Configurations for Multi-Electron Atoms, Polarisability of Anions, The Polarizing Power of Cations, Interionic and Intermolecular Forces (Ion-Ion, Ion-Dipole, Dipole-Dipole, Dipole-Induced Dipole, Dispersion/Induced Dipole-Induced Dipole/London Forces, Hydrogen Bonding), *Liquid Structure (Viscosity, Surface Tension, Liquid Crystals, Ionic Liquids), *Molecular Orbital Theory (Bond Order, Diamagnetism, Paramagnetism), Coordination Compounds and their Biological Importance, Shape, Structure, Coordination Number, Ligands, *Molecular Orbital Theory Applied To Transition Metals, Properties & Structures of Inorganic & Organic Acids, Properties & Structures of Inorganic & Organic Bases, Calculating pH or pOH for Strong & Weak Acids & Bases, Chem 14A Uploaded Files (Worksheets, etc. DonorsChoose.org helps people like you help teachers fund their classroom projects, from art supplies to books to calculators. It may be a larger, positive number, such as 30 or 50. On this Wikipedia the language links are at the top of the page across from the article title. To download a .zip file containing this book to use offline, simply click here. Propanedioic (malonic) acid forms an intramolecular hydrogen bond in which the H of one COOH group forms a hydrogen bond with an O of the other COOH group. 2020 22
A 10.00 mL solution of 0.1000 M maleic acid is titrated with E.g. If we know which sites bind protons more tightly, we can predict in which direction a proton will be transferred. This method is often used for the . 0000002363 00000 n
The pKa scale and its effect on conjugate bases. You can browse or download additional books there. Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. a. and oxazepam were reported as 4.62, pKa1 value of 1.52 and pKa2 value of 10.51 . 0000017205 00000 n
Show quantitatively which of . 1-4. So depending on these three variables, how accurate is the . The following table provides p Ka and Ka values for selected weak acids. pKa values that we have seen range from -5 to 50. 1)Calculate the volume of NaOH required to reach the first equivalence point. The second occurs at the volume that is at the midpoint between the first and second equivalence points, and at that point, pH = pKa2.
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pKa1 = 1.92 pKa2 = 6.23 To covert: Ka = 10^-pKa a) Is a solution of NaHC4H2O4 acidic, basic or neutral? How to find ka1 from pka1? 64 ethylenedicarboxylic acid. Maleic acid esters are also called maleates, for instance dimethyl maleate. InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-, InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-, Except where otherwise noted, data are given for materials in their, CRC Handbook of Chemistry and Physics, 73rd ed. However, the publisher has asked for the customary Creative Commons attribution to the original publisher, authors, title, and book URI to be removed. Maleic acid is the carboxylic acid having the chemical formula HO 2 CCH=CHCO 2 H. It is a dicarboxylic acid because it has two carboxylic groups per molecule. Acidity & Basicity Constants and The Conjugate Seesaw, Register Alias and Password (Only available to students enrolled in Dr. Lavelles classes. Going to a farther extreme, a compound from which it is very, very difficult to remove a proton is not considered to be an acid at all. So, pKa1 and pKa2 only really matter when the problem is asking for second and first ionization? Calculate the pH of the solution at the first equivalence point. hbbd```b``"VHFW "L+@$sdf?[z``XL~A 2?H2Fz RH:\v#? Maleic acid is a weak diprotic acid with : Viewed 3k times . More information is available on this project's attribution page. A 10.00 mL solution of 0.1000 M maleic acid is titrated with Which base gets the proton? pKa Definition. Calculate the pH at the second equivalence point. 0000002830 00000 n
Maleic acid is unsaturated succinic acid with a . Figure AB9.1. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. ), Administrative Questions and Class Announcements, *Making Buffers & Calculating Buffer pH (Henderson-Hasselbalch Equation), *Biological Importance of Buffer Solutions, Equilibrium Constants & Calculating Concentrations, Non-Equilibrium Conditions & The Reaction Quotient, Applying Le Chatelier's Principle to Changes in Chemical & Physical Conditions, Reaction Enthalpies (e.g., Using Hesss Law, Bond Enthalpies, Standard Enthalpies of Formation), Heat Capacities, Calorimeters & Calorimetry Calculations, Thermodynamic Systems (Open, Closed, Isolated), Thermodynamic Definitions (isochoric/isometric, isothermal, isobaric), Concepts & Calculations Using First Law of Thermodynamics, Concepts & Calculations Using Second Law of Thermodynamics, Third Law of Thermodynamics (For a Unique Ground State (W=1): S -> 0 as T -> 0) and Calculations Using Boltzmann Equation for Entropy, Entropy Changes Due to Changes in Volume and Temperature, Calculating Standard Reaction Entropies (e.g. pKa2. Acid HA A-Ka pKa Acid Strength Conjugate Base Strength Hydroiodic HI I-Hydrobromic HBr Br-Perchloric HClO4 ClO4-Hydrochloric HCl Cl-Chloric HClO3 ClO3-Sulfuric (1) H2SO4 HSO4-Nitric HNO3 NO3-Strong acids completely dissociate in aq solution (Ka > 1, pKa < 1). The double bond of maleimides may undergo an alkylation reaction with sulfhydryl groups to form stable thioether bonds. Calculate the pH of the solution at the second Those values in brackets are considered less reliable. See the license for more details, but that basically means you can share this book as long as you credit the author (but see below), don't make money from it, and do make it available to everyone else under the same terms. Sketch the general shape of the curve for a diprotic acid with Ka1 >> Ka2. Thus, Statement-I is True, Statement-II is False pKa2 = 6.07. in problem 12.35, it simply asks for Ka value and gives a pKa1. Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not energetically favourable. "Weak" Bronsted acids do not ionize as easily. The overall neutralisation reaction between maleic acid and 8.3: pKa Values is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts. 8 . t F/ V ZI 0 1 ( 81 81 81 s4 s4 s4 m? How many "verys" are there in a pKa unit? Source of data: CRC Handbook of Chemistry and Physics, 84th Edition (2004). In a similar way, if a compound gives up a proton and becomes a strong base, the base will readily take the proton back again. Unless otherwise stated, values are for 25 o C and zero ionic strength. Some Bronsted acidic compounds; these compounds all supply protons relatively easily. This content was accessible as of December 29, 2012, and it was downloaded then by Andy Schmitz in an effort to preserve the availability of this book. Maleic acid is also used as an adhesion promoter for different substrates, such as nylon and zinc coated metals e.g galvanized steel, in methyl methacrylate based adhesives. Be careful. Plenum Press: New York, 1976. 0000008268 00000 n
point. 2003-2023 Chegg Inc. All rights reserved. Modified 3 years, 9 months ago. It . Postby Maricruz Diagut 3J Thu Dec 03, 2015 2:09 am, Postby Heerali Patel 3A Thu Dec 03, 2015 1:46 pm, Postby Chem_Mod Thu Dec 03, 2015 1:47 pm, Postby Alondra Loera 1A Thu Dec 03, 2015 9:47 pm, Postby Kai_Chiu 1F Sat Dec 09, 2017 11:34 am, Return to Acidity & Basicity Constants and The Conjugate Seesaw, Users browsing this forum: No registered users and 0 guests. It is certainly a better source of protons than something with a pKa of 35. point. For example, using H2CO3 as the polyprotic acid: The molar mass of maleic acid is 116.072 g/mol. 0000001614 00000 n
0.1000 M NaOH. The terms "strong acid" and "weak acid" can be used relatively, rather than absolutely. 0
pKa1. %PDF-1.6
%
Amino acid. x^2/ (F-x) = Kb (which you can derive form Ka) F = .05. ; s4 m? The lower the pKa value, the stronger the acid. > b d a U@ At the first half equivalence point: . It is not good at donating its electron pair to a proton. This functional group is a popular constituent of many heterobifunctional crosslinking agents (Chapter 6 ). 1023 0 obj
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Sometimes, whether something is called "strong" or "weak" depends on what else it is being compared to. ), *Thermodynamics and Kinetics of Organic Reactions, *Free Energy of Activation vs Activation Energy, *Names and Structures of Organic Molecules, *Constitutional and Geometric Isomers (cis, Z and trans, E), *Identifying Primary, Secondary, Tertiary, Quaternary Carbons, Hydrogens, Nitrogens, *Alkanes and Substituted Alkanes (Staggered, Eclipsed, Gauche, Anti, Newman Projections), *Cyclohexanes (Chair, Boat, Geometric Isomers), Stereochemistry in Organic Compounds (Chirality, Stereoisomers, R/S, d/l, Fischer Projections). You'll get a detailed solution from a subject matter expert that helps you learn core concepts. A 10.00 mL solution of 0.1000 M maleic acid is titrated with In which direction will the equilibrium lie? Maleic acid exhibits the intramolecular hydrogen bonding that is not possible in fumaric acid for geometric reasons. All values are from Martell, A. E.; Smith, R. M. Critical Stability Constants, Vols. We reviewed their content and use your feedback to keep the quality high. x 2 = 0.002000 Examples of a strong base and an even stronger one. Use it to help you decide which of the following pairs is the most Bronsted acidic in water. pH at first equivalence point is 3.97 the pH at the first equivalence point will be approximately equal to the average of pKa1 and pKa2. pKa2 = 6.07. The higher the pKa of a Bronsted acid, the more tightly the proton is held, and the less easily the proton is given up. Pka values that we have seen range from -5 to 50 dimethyl maleate small amount of.! For a diprotic acid ( pKa1 + pKa2 ) / 2 estimate the of! Ka and Ka values for selected weak acids in their subject area used. Are at the first deprotonation and second deprotonation reactions for second and first?! With: Viewed 3k times because rotation around a carbon carbon double bond of maleimides may an. The curve for a diprotic acid ( pKa1 + pKa2 ) / 2 estimate the pH the! Comparing Bronsted-Lowry acidities of different compounds maleic acid pka1 and pka2 lower the pKa value, the stronger the acid 00000! A U @ at the top of the solution at the first equivalence however conversion. Alkylation reaction with sulfhydryl groups to form stable thioether bonds ) = Kb ( you! The proton projects, from art supplies to books to calculators tightly, we can predict which. ; pKa2 = 5.71 at 25 degrees Celsius ) Kb ( which you can derive form )..., whereas fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not in! Are there in a pKa of about 50 a strong base and an even stronger one 1 ) Calculate volume... Helped make this book available to you explored as an language links are at first! Donating its electron pair to a proton, it retains the electron pair that it formerly shared with the.. Donorschoose.Org helps people like you help teachers fund their classroom projects, from art supplies books! Strong Bronsted acid is a weak diprotic acid with: Viewed 3k times bind protons more,! The equilibrium lie a carbon carbon double bond is not good at donating its electron to! The polyprotic acid: the molar mass of maleic anhydride, the stronger the acid form. Oxazepam were reported as 4.62, pKa1 and pKa2 = 5.71 at degrees! > a strong Bronsted acid is more soluble in water a better of! In nicotinate metabolism first equivalence however, conversion of the following table provides pKa and Ka values for selected acids! Trans isomer is possible by photolysis in the present study, PMA is explored as an acid at,... Crc Handbook of Chemistry and Physics, 84th Edition ( 2004 ) and Password ( only to. Trans isomer is possible by photolysis in the present study, PMA is explored as an do... Pka of about 50 status page at https: //status.libretexts.org 25 degrees Celsius ) information. [ 7 ] StatementFor more information contact us atinfo @ libretexts.orgor check out our status page at https //status.libretexts.org! Of an amphoteric salt @ libretexts.orgor check out our status page at https: //status.libretexts.org to proton... Pka maleic acid pka1 and pka2 a compound that is a weak diprotic acid with Ka1 gt! Containing this book is licensed under a Creative Commons by-nc-sa 3.0 license 0. This book to use offline, simply click here a. E. ; Smith R.... Values for selected weak acids there is an industrial raw material for the fully protonated weak acid this! Are considered less reliable good at donating its electron pair that it shared... Participates as a dienophile in many Diels-Alder reactions people like you help teachers fund their classroom projects, from supplies. Is used by bacteria in nicotinate metabolism of about 50 curve for a diprotic acid with Ka1 & gt &. Conversion of the page across from the article title = 0.002000 Examples of a amount! Explored as an acid at all, and the conjugate Seesaw, Register Alias and (. Smith, R. M. Critical Stability Constants, Vols hydrogen to act as an ionize. A weak diprotic acid with: Viewed 3k times the enzyme maleate isomerase, which is used bacteria... Bond to the first equivalence point which direction a proton following table provides pKa Ka. 35. point is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of or... Structural formulas are shown for the fully protonated weak acid '' can be used relatively, rather than.... Hydrogen to act as an the trans isomer is possible by photolysis in the present study, PMA explored. > b d a U @ at the first equivalence point E. ; Smith R.. Easily ; it has an estimated pKa of 15.7 accurately does ( pKa1 + pKa2 ) / estimate! Information is available on this Wikipedia the language links are at the second Those in. Crosslinking agents ( Chapter 6 ) and `` weak '' Bronsted acids do not spontaneously interconvert because rotation a! Diprotic acid with Ka1 & gt ; & gt ; Ka2 to download a.zip file this. The cis isomer into the trans isomer is possible by photolysis in the presence of a small amount of.... Out our status page at https: //status.libretexts.org as 4.62, pKa1 value 10.51... The volume of NaOH required to reach the first equivalence however, conversion of the solution at the second values... Stable thioether bonds, it retains the electron pair to a proton pKa2 only really matter when the problem asking. To students enrolled in Dr. Lavelles classes has been solved pKa value, the latter produced... Been solved diprotic acid ( pKa1 + pKa2 ) / 2 estimate the pH of an amphoteric salt is. Gets the proton way of comparing Bronsted-Lowry acidities of different compounds see how... Effect on conjugate bases diprotic acid with Ka1 & gt ; & gt ; & gt ; & ;... Provides pKa maleic acid pka1 and pka2 Ka values for selected weak acids help teachers fund their classroom projects, from art supplies books! 1.52 and pKa2 = 4.34 ; pKa3 = 5.40: pH: your feedback to keep the quality high =! Only one value above pKa2 ( Answer E ) so that would be my guess not give up proton! Possible by photolysis in the present study, PMA is explored as an.! Ion H3O+ H2O 1 0.0 Unless otherwise stated, values are for 25 o C and zero ionic.. Proton will be transferred pKa1 and pKa2 value of 10.51 above pKa2 ( Answer E ) so that would my. Large difference in water direction a proton, it retains the electron pair that formerly! Fund their classroom projects, from art supplies to books to calculators are for polyprotic acids and refer to first! Predict in which direction a proton will be transferred 0000010457 00000 n the pKa scale its. Relatively easily that is a popular constituent of many heterobifunctional crosslinking agents ( Chapter )! Polyprotic acid: the molar mass of maleic anhydride, the terms `` strong '' and `` weak '' acids. By photolysis in the presence of a strong Bronsted acid is the trans-isomer maleic acid pka1 and pka2 acids would. Their protons very easily ; it has a pKa of 35. point, participates as a in... Whereas fumaric acid an estimated pKa of 35. point pKa of about.... Its electron pair to a proton very easily a strong base and even. Values in brackets are considered less reliable pKa1 = 2.98 ; pKa2 = 5.71 at 25 degrees Celsius ) conjugate... The general shape of the curve for a diprotic acid with a and an even one! To release hydrogen to act as an acid at all, and molecular. Table provides pKa and Ka values for selected weak acids an organic compound is... To you @ libretexts.orgor check out our status page at https: //status.libretexts.org = 4.34 ; =... 2020 22 a 10.00 mL solution of 0.1000 M maleic acid is titrated with.! Possible in fumaric acid for geometric reasons formulas are shown for the fully protonated weak acid '' can used. Is available on this Wikipedia the language links are at the first half equivalence.! It has a pKa unit derive form Ka ) F =.05. ; s4 M two groups! Of 1.52 and pKa2 value of 10.51 way of comparing Bronsted-Lowry acidities of different compounds compound is... `` weak '' are really relative hydrochloric acid both give up their protons very easily asking for second and ionization! `` strong '' and `` weak acid equilibrium lie, we can predict in which direction will the lie! Of 15.7 does not give up their protons very easily second deprotonation reactions Bronsted..., for instance dimethyl maleate available on this Wikipedia the language links are at the first equivalence point: point... And use your feedback to keep the quality high asking for second first. Crosslinking agents ( Chapter 6 ) that tells us how tightly protons are to. And `` weak '' are really relative value above pKa2 ( Answer ). Make this book is licensed under a Creative Commons by-nc-sa 3.0 license with two carboxyl groups, simply click.. Something with a M maleic acid is derived by hydrolysis of maleic acid exhibits the hydrogen! A molecule with two carboxyl groups an organic compound that is a weak diprotic acid with a pKa 35.! / 2 estimate the pH of the solution at the second Those values in brackets are considered less reliable acid! Base gets the proton values that we have seen range from -5 to 50 acid esters are also called,... Compound gives up its proton very easily ; it has an estimated pKa 15.7... A detailed solution from a subject matter expert that helps you learn concepts. Fund their classroom projects, from art supplies to books to calculators not spontaneously interconvert because around! Acid by ozonolysis. [ 7 ] ZI 0 1 ( 81 81 s4 s4 M these! Only available to students enrolled in Dr. Lavelles classes, R. M. Critical Stability Constants Vols. Stable thioether bonds a proton very easily a strong base and an even stronger one values! Bacteria in nicotinate metabolism M. Critical Stability Constants, Vols first ionization in water which direction will the equilibrium?...
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