Interpretation:
The p Ka values of acidic hydrogen of the given species are to be determined using table 3.1.
Concept introduction:
The strength of an acid is generally described in terms of acidity constant
A large value of
The value of pKa of a reagent can be mathematical defined as
The higher is the dissolution constant, that is, the reagent can produce more ions when dissolved in water, the stronger is the acid. Thus, by the above relation, strong acids have low pKa.
The stronger the acid, the weaker is its conjugate base.
Larger the value of pKa of the conjugate base, the stronger is the acid.
The
Alcohol is too weak an acid to ionize in the presence of strong sulfuric acid.
The ester is nonelectrolyte and will not ionize in water.
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Chapter 3 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- 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.arrow_forwardWhich of the following two acids has the stronger conjugate base? Nitrous acid, Ka = 7.1 x 10–4 Phenol, Ka = 1.0 x 10–10 The strength of the conjugate base cannot be obtained from the information given. Nitrous acid, because it has a larger Ka value. Nitrous acid, because it has a smaller Ka value. Phenol, because it has a larger Ka value. Phenol, because it has a smaller Ka value.arrow_forwardWrite down the reaction of ethanoic acid with water and identify the conjugate base.arrow_forward
- Why is HCl so acidic? For example, why is H-Cl more acidic than H-S-CH3? Isn't the conjugate base's negative charge more stabilized with a sulfur and extra methyl group (by the induction effect)? While Cl is more electronegative than Sulfur, I would assume Cl being alone as its own ion would make it less stable.arrow_forward(a) Given that Ka for acetic acid is 1.8 x 10-5 and that forhypochlorous acid is 3.0 x 10-8, which is the stronger acid?(b) Which is the stronger base, the acetate ion or the hypochloriteion? (c) Calculate Kb values for CH3COO- and ClO-.arrow_forwardFor a solution of formic acid, a weak acid with a pKa of 8.74, at what pH will the concentration of formic acid be equal to the concentration of formate, the conjugate weak base of formic acid. Report the value using 3 significant figures.arrow_forward
- Compare the pH of propionic acid and nitric acid when they are dissolved in water at a concentration of 20 mM. This should include writing a balanced equation describing the acid-base reactions involved, calculation of the pKa for both, calculation of pH, and calculation of the percent dissociation of both.arrow_forward1a) Consider the reaction AH(+) + H₂O A: + H3O+). For the following named acids: a) draw the structure of the acid, b) give the approximate pKa of the conjugate acid in units of 5, c) give the name of the conjugate base, and d) draw the structure of the conjugate base. p-Toluenesulfonic acid acid Conjugate base Imidazolium cation pka_ pKa iso-Propanol pKa Acetylene pKaarrow_forwardThe hydride ion is very basic and reacts readily with compounds having even weakly acidic protons to form H2. True or false?arrow_forward
- Arrange the given molecules by increasing acidity. Elaborate these in terms of their partial charges and their inductive effects.arrow_forwardCalculate the pH of a 0.35 M solution of hydrocyanic acid (HCN), which has a pKa of 9.31. Your answer should have 3 significant figures (i.e. 9.99).arrow_forwardWrite the acid dissociation constant expression (Ka ) for the dissociation of HCN.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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