Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 3, Problem 3.14P
Interpretation Introduction
(a)
Interpretation:
The dissociation constant of an acid that has
Concept introduction:
Dissociation constant
The formula used to calculate the value of
Interpretation Introduction
(b)
Interpretation:
The dissociation constant of an acid that has
Concept introduction:
Dissociation constant
The formula used to calculate the value of
Interpretation Introduction
(c)
Interpretation:
The dissociation constant of an acid that has
Concept introduction:
Dissociation constant
The formula used to calculate the value of
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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…
Calculate the equilibrium constant for the acid–base reaction between the reactants in each of the following pairs: (a) HCl + H2O (b) CH3COOH + H2O (c) CH3NH2 + H2O (d) CH3N+H3 + H2O
Consider two acids: HCO2H (formic acid, pKa = 3.8) and pivalic acid [(CH3)3CCO,H, pK = 5.0].
(a) Which acid has the larger K? (b) Which acid is the stronger acid? (c) Which acid forms the
stronger conjugate base? (d) When each acid is dissolved in water, for which acid does the
equilibrium lie further to the right?
%3D
The pKa values in Table 2.1 span a large range (-7 to 50). The pK, scale is logarithmic.
small difference in pK, translates into a large numerical difference, For example, the diffe
between the pK, of NH3 (38) and CH2=CH, (44) is six pKa units. This means that NH, is
one million times more acidic than CH,=CH,.
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 3.1PCh. 3 - Prob. 3.2PCh. 3 - Prob. 3.3PCh. 3 - Prob. 3.4PCh. 3 - Prob. 3.5PCh. 3 - Prob. 3.6PCh. 3 - Prob. 3.7PCh. 3 - Prob. 3.8PCh. 3 - Prob. 3.9PCh. 3 - Prob. 3.10P
Ch. 3 - Prob. 3.11PCh. 3 - Prob. 3.12PCh. 3 - Prob. 3.13PCh. 3 - Prob. 3.14PCh. 3 - Prob. 3.15PCh. 3 - Prob. 3.16PCh. 3 - Prob. 3.17PCh. 3 - Prob. 3.18PCh. 3 - Prob. 3.19PCh. 3 - Prob. 3.20PCh. 3 - Prob. 3.21PCh. 3 - Prob. 3.22PCh. 3 - Prob. 3.24PCh. 3 - Prob. 3.25PCh. 3 - Prob. 3.26PCh. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Prob. 3.30PCh. 3 - Prob. 3.31PCh. 3 - Prob. 3.32APCh. 3 - Prob. 3.33APCh. 3 - Prob. 3.34APCh. 3 - Prob. 3.35APCh. 3 - Prob. 3.36APCh. 3 - Prob. 3.37APCh. 3 - Prob. 3.38APCh. 3 - Prob. 3.39APCh. 3 - Prob. 3.40APCh. 3 - Prob. 3.41APCh. 3 - Prob. 3.42APCh. 3 - Prob. 3.43APCh. 3 - Prob. 3.44APCh. 3 - Prob. 3.45APCh. 3 - Prob. 3.46APCh. 3 - Prob. 3.47APCh. 3 - Prob. 3.48APCh. 3 - Prob. 3.49APCh. 3 - Prob. 3.50APCh. 3 - Prob. 3.51APCh. 3 - Prob. 3.52APCh. 3 - Prob. 3.53APCh. 3 - Prob. 3.54APCh. 3 - Prob. 3.55APCh. 3 - Prob. 3.56APCh. 3 - Prob. 3.57APCh. 3 - Prob. 3.58APCh. 3 - Prob. 3.59APCh. 3 - Prob. 3.60AP
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- For conjugate acidbase pairs, how are Ka and Kb related? Consider the reaction of acetic acid in water CH3CO2H(aq)+H2O(l)CH3CO2(aq)+H3O+(aq) where Ka = 1.8 105 a. Which two bases are competing for the proton? b. Which is the stronger base? c. In light of your answer to part b. why do we classify the acetate ion (CH3CO2) as a weak base? Use an appropriate reaction to justify your answer. In general, as base strength increases, conjugate acid strength decreases. Explain why the conjugate acid of the weak base NH3 is a weak acid. To summarize, the conjugate base of a weak acid is a weak base and the conjugate acid of a weak base is a weak acid (weak gives you weak). Assuming Ka for a monoprotic strong acid is 1 106, calculate Kb for the conjugate base of this strong acid. Why do conjugate bases of strong acids have no basic properties in water? List the conjugate bases of the six common strong acids. To tie it all together, some instructors have students think of Li+, K+, Rb+, Cs+, Ca2+, Sr2+, and Ba2+ as the conjugate acids of the strong bases LiOH, KOH. RbOH, CsOH, Ca(OH)2, Sr(OH)2, and Ba(OH)2. Although not technically correct, the conjugate acid strength of these cations is similar to the conjugate base strength of the strong acids. That is, these cations have no acidic properties in water; similarly, the conjugate bases of strong acids have no basic properties (strong gives you worthless). Fill in the blanks with the correct response. The conjugate base of a weak acid is a_____base. The conjugate acid of a weak base is a_____acid. The conjugate base of a strong acid is a_____base. The conjugate acid of a strong base is a_____ acid. (Hint: Weak gives you weak and strong gives you worthless.)arrow_forwardAcid-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_forwardBenzoic acid (C6H5COOH) and aniline (C6H5NH2) areboth derivatives of benzene. Benzoic acid is an acid withKa = 6.3 x10-5 and aniline is a base with Ka = 4.3 x10-10. (a) What are the conjugate base of benzoic acid andthe conjugate acid of aniline? (b) Anilinium chloride(C6H5NH3Cl) is a strong electrolyte that dissociates intoanilinium ions (C6H5NH3+) and chloride ions. Which willbe more acidic, a 0.10 M solution of benzoic acid or a 0.10M solution of anilinium chloride? (c) What is the value ofthe equilibrium constant for the following equilibrium?C6H5COOH(aq) + C6H5NH2(aq) ⇌ C6H5COO-(aq) + C6H5NH3+(aq)arrow_forward
- What is the correct equilibrium constant expression for the following reaction? NH3(aq) + H₂O(1) ⇒NH4*(aq) + OH¯(aq) O O (A) Ke (B) Kc (c) Ke (D) Kc (E) Kc - = = = [NH3] [H₂O] [NH4]+[OH]- [NH4+][OH-] [NH3] [NH4+] [OH [NH3] [H₂O] [NH3] [NH₂+] [OH-] 4 [NH₁+OH [NH3]arrow_forward(i) What is the Arrhenius definition of an acid, give an example Why is NH3 considered a base according to Bronsted-Lowry theory?arrow_forward(a) Given that Ka for acetic acid is 1.8 x 10-5 and that hypochlorous acid is 3.0 x10-8 , which is a stronger acid? (b) Which is the stronger base, the acetate ion or the hypochlorite ion? (c) calculate the Kb values for the CHCOO- and ClO- .arrow_forward
- 4, . Consider the following equilibrium: base + -H H-Base Which of the following base(s) would favour the product in this reaction? Он CH;O NH3 NH2 CH3CO2 (1) (II) (III) (IV) (V) (a) | (b) IV (c) I, IV and V (d) I and II (e) IIl and IVarrow_forwardIdentify the Lewis acid and Lewis base among the reactantsin each of the following reactions:(a) Fe1ClO423(s) + 6 H2O(l)⇌[Fe(H2O)6]3+(aq)+ 3 ClO4-(aq)(b) CN-(aq) + H2O(l) ⇌ HCN(aq) + OH-(aq)(c) (CH3)3N(g) + BF3(g) ⇌ (CH3)3NBF3(s)(d) HIO(lq) + NH2-(lq)⇌ NH3(lq) + IO-1(lq)(lq denotes liquid ammonia as solvent)arrow_forwardIn the following reactions, indicate the acid, base, conjugate acid, and conjugate base. (a)HF + NH3→NH4++ F – (b)NaHSO4+ HClO3⇌H2SO4+ NaClO3arrow_forward
- Which, if any, of the following statements are true? (a) The stronger the base, the smaller the pKb. (b) The stronger the base, the larger the pKb. (c) The stronger the base, the smaller the Kb. (d) The stronger the base, the larger the Kb. (e) The stronger the base, the smaller the pKa of its conjugate acid. (f) The stronger the base, the larger the pKa of its conjugate acid.arrow_forwardThe Keq for the reaction: A + B ↔ AB is 2.163 What is the Keq for 2 + AB ↔ 2 A + 2 Barrow_forwarddentify the acid-base conjugate pairs in each of the following reactions: (a) CH3COO HCN CH3COOH CN (b) HCO HCO H2CO3 CO (c) H2PO NH3 HPO NH (d) HClO CH3NH2 CH3NH ClO (e) CO H2O HCO OHarrow_forward
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