Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a rnonoanion and one for the second dissociation into a dianion . For oxalic acid, HO2C-CO.H, the first ionization constant has pKaj = 1.2 and the second ionization constant has pKaz = 4.2. Why is the second carboxyl group so much less acidic than the first?
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- Acid-Base Equilibria Many factors contribute to the acidity of organic compounds. Electronegativity, resonance, induction, hybridization, aromaticity, and atomic size, all play a role. In the following comparisons, you are asked to identify the factor(s) that would be most important to analyze when predicting relative acidity, and then to predict the trend in acidity and pKa values. For each of the following pairs of compounds answer the following two multiple-choice questions. 1. What factor(s) are the most important to consider when predicting the relative acidity of the two compounds? a. Electronegativity of the atom possessing the hydrogen. b. Resonance stabilization of the anionic conjugate base. c. Inductive stabilization of the anionic conjugate base. d. Hybridization of the atom possessing the hydrogen. e. The atomic size of the atom possessing the hydrogen.COHSOH(ag) + H2On + CeHsO (aq) + H3O*(a9) Ka= 1.12 x 10-10 (a) Phenol is a weak acid that partially dissociates in water according to the equation above. Write the equilibrium-constant expression for the dissociation of the acid in water. (b) What is the pH of a 0.75 M CaHsOH(ag) solution? (C) For a certain reaction involving CaHsOH(ag) to proceed at a significant rate, the phenol must be primarily in its deprotonated form, C3H5O (eg). In order to ensure that the CsHsOH(aq) is deprotonated, the reaction must be conducted in a buffered solution. On the number scale below, circle each pH for which more than 50 percent of the phenol molecules are in the deprotonated form (CoHsO (aq). Justify your answer. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Justification: (d) CeHsOH(ag) reacts with NaOH(ag). Write a net ionic equation representing this reaction (aka: invasion equation). (e) What is the pH of the resulting solution when 30 mL of 0.40 M CSH5OH(aq) is added to 25 mL of 0.60 M NAOH. Show all work…The disinfectant phenol, C₆H₅OH, has a pKₐ of 10.0 in wa-ter, but 14.4 in methanol. (a) Why are the values different? (b) Is methanol is a stronger or weaker base than water? (c) Write the dissociation reaction of phenol in methanol. (d) Write an expres-sion for the autoionization constant of methanol.
- Determine the principal species at the following pH levels for Nitrilotriacetic acid. The most protonated form is C6H10NO6+. pH= 1,2,3,4,10. pK1 = 1.0, pK2 = 1.81, pK3 = 2.52, pK4 = 9.46.For the acid-base reactions below, fill in the boxes by providing the structure of the conjugate base or conjugate acid, and estimating the value of the equilibrium constant, Keq. ' + SH 요 요 ее в осно + Kea но = Kea = Keq = рказ = 5 + CH3OH + H₂ + pka = 35HN3(aq) + H2O(l) ⇌ N3-(aq) + H3O(aq) Calculate the hydronium ion concentration and pH of a 0.045 M solution of chloroacetic acid. (Ka = 1.3 x 10-3). Chloroacetic acid is a monoprotic acid, i.e. it reacts with water in a 1:1 mole ratio.
- 4. A student has prepared 0.05 M solution of CH3-C=CH and has added to it 0.05 M solution of potassium tert-butoxide (K" O-C(CH3)3). (i) Write the equation for the acid-base reaction that might occur. (ii) With curved arrows track the movements of electron pairs. (iii) Assign Base, Acid, Conjugate acid for the base, Conjugate base for the acid. (iv) Calculate the percentage of deprotonated methyl acetylene taking into account that pKa of the conjugate acid of potassium tert-butoxide equals 18 and pKa of methyl acetylene equals 24.Disulfides are compounds that have S¬ S bonds, like peroxides have O¬ O bonds. Thiols are organic compounds that have the general formula R¬ SH, where R is a generic hydrocarbon. The SH- ion is the sulfur counterpart of hydroxide, OH-. Two thiols can react to make a disulfide, R¬ S¬ S¬ R. If you wanted to convert a disulfide to two thiols, should you add a reducing agent or oxidizing agent to the solution?For the following acid-base reaction, (1) predict the products, showing both reactants and products complete Lewis structures and arrows showing electron flow; (2) label each structure with the lowing: Bronsted acid, Bronsted base, conjugate acid, conjugate base; (3) give a brief definition of a ronsted acid and Bronsted base; (4) predict the direction of the equilibrium and justify your answer. HC0OH + CH3 Nta PRん106Y pkb = 3.36
- Liquid ammonia (anhydrous NH3(0)) is often used as a solvent. Like water, ammonia undergoes autoionization by the transfer of a proton: 2NH3 = NH4+ + NH2" K = 1x10-33 at -50°C Since ammonia is better proton acceptor than water, the ionization of acids is relatively enhanced in liquid ammonia. For example, acetic acid is a strong acid in liquid ammonia. Estimate [NH4+] (mol/L) in pure (i.e. neutral) liquid ammonia at -50°C. mol/L Submit Answer Tries 0/5 Calculate [NH4+] (mol/L) in a 7.07x10-5 M solution of acetic acid in liquid ammonia at -50°C. mol/L Submit Answer Tries 0/5 Estimate [NH2] (mol/L) in a 7.07x10-5 M solution of acetic acid in liquid ammonia at -50°C.Liquid ammonia (anhydrous NH3(l)) is often used as a solvent. Like water, ammonia undergoes autoionization by the transfer of a proton: 2NH3 NH4+ + NH2- K = 1×10-33 at -50°C Since ammonia is better proton acceptor than water, the ionization of acids is relatively enhanced in liquid ammonia. For example, acetic acid is a strong acid in liquid ammonia. a) Estimate [NH4+] (mol/L) in pure (i.e. neutral) liquid ammonia at -50°C. b) Calculate [NH4+] (mol/L) in a 6.29×10-2 M solution of acetic acid in liquid ammonia at -50°C. c) Estimate [NH2-] (mol/L) in a 6.29×10-2 M solution of acetic acid in liquid ammonia at -50°C.3. In biology, evergy is stored as adenosime triphosphate (ATP or ATP+). When this compound hydrolyses, a leturns to its low energy form, adenosine diphosphate (ADT, or ADT¹"): 3- 4- ATP ² (aq) + H₂O → ADP + HPO₂²² + H₂O + and Gran AG At 37°C and pH=7₁0, AH₂ = -20 kJ. Mol" 31 RJ.mol" for this process. (a) How much non-expansion work is ducilable per mole of ATP hydrolysed. ? (2) ($) Calculate and explain the sign of (3) AS rxn for this process at 37°C and pte=7