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Study Guide And Student Solutions Manual For Organic Chemistry, Books A La Carte Edition (7th Edition)
- Substituted phenols show substituent effects similiar to substituted benzoic acids. Should the pKa of phenol A, one of the naturally occurring phenols called urushiols isolated from poison ivy, be higher or lower than the pKa of phenol (C6H5OH, pKa = 10)? Explain.arrow_forwardThe pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.a. Which carboxyl group is the stronger acid?b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.arrow_forwardThe pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98. a. Which carboxyl group is the stronger acid? b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.arrow_forward
- Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.arrow_forwardConsider 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 pKa = 0.17arrow_forwardAcetic acid can also react as a very weak base (pKb = 20). Two different sites on acetic acid might become protonated to give the conjugate acid. Draw both of these possible conjugate acids, and explain (resonance) why the correct one is more stable. Calculate the pKa of this conjugate acid.arrow_forward
- Draw the structure of chloric and chlorous acid and predict their pKa values using Pauling's rules.arrow_forwardDicarboxylic acids have two pKa's.- For maleic acid (cis-2-butenedioic acid) these are pKa1 = 2.0, and pKa2 = 6.3- For fumaric acid (trans-2-butenedioic acid) these are pKa1 = 3.0, and pKa2 = 4.5 Which factor best explains why the cis-isomer has a smaller pKa1 and a larger pKa2 than the trans-isomer? a. Intramolecular hydrogen bonding b. Intramolecular steric hindrance c. Selective solvation in water d. Intramolecular dipole repulsionarrow_forwardUsing your knowledge of general chemistry and organic chemistry, answer the following questions: Predict the relative acidities within each of the following groups, then identify the conjugate bases, and finally predict their relative leaving group abilities HClO3 and HClO2 PH3 and H2S [NH4]+ and [H3O]+ Explain why the trifluoromethane sulfonate (TfO-) ion is a better leaving group than the methanesulfonate (MsO-) ion.arrow_forward
- Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH) is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid (CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).arrow_forwardExplain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH)is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid(CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).arrow_forwardUsing pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forward