Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 4.3, Problem 4.5P
For each value of Ka, calculate the corresponding value of pKa. Which compound is the stronger acid?
- (a) Acetic add, Ka = 1.74 × 10–5
- (b) Chloroacetic acid, Ka= 1.38 × 10–3
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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?
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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,.
(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- .
(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-.
Chapter 4 Solutions
Organic Chemistry
Ch. 4.2 - For each conjugate acid-base pair, identify the...Ch. 4.2 - Write these reactions as proton-transfer...Ch. 4.2 - Following is a structural formula for guanidine,...Ch. 4.2 - Write an equation to show the proton transfer...Ch. 4.3 - For each value of Ka, calculate the corresponding...Ch. 4.4 - Predict the position of equilibrium and calculate...Ch. 4.5 - Calculate Keq for a reaction with G0 = 17.1 kJ/mol...Ch. 4.6 - Acid-Base Equilibria Many factors contribute to...Ch. 4.6 - What is the relative trend in acidity and pKa of...Ch. 4.7 - Write an equation for the reaction between each...
Ch. 4 - For each conjugate acid-base pair, identify the...Ch. 4 - Complete a net ionic equation for each...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Prob. 4.12PCh. 4 - In acetic acid, CH3COOH, the OH hydrogen is more...Ch. 4 - Which has the larger numerical value? (a) The pKa...Ch. 4 - In each pair, select the stronger acid. (a)...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - If the G for a reaction is 4.5 kcal/mol at 298 K,...Ch. 4 - Calculate the Keq for the following reactions from...Ch. 4 - Prob. 4.20PCh. 4 - Answer true or false to the following statements...Ch. 4 - In each of the following three reaction coordinate...Ch. 4 - The acid-base chemistry reaction of barium...Ch. 4 - Unless under pressure, carbonic acid (H2CO3) in...Ch. 4 - Prob. 4.25PCh. 4 - Acetic acid, CH3COOH, is a weak organic acid, pKa...Ch. 4 - Benzoic acid, C6H5COOH (pKa 4.19), is only...Ch. 4 - Prob. 4.28PCh. 4 - One way to determine the predominant species at...Ch. 4 - Will acetylene react with sodium hydride according...Ch. 4 - Prob. 4.31PCh. 4 - For each equation, label the Lewis acid and the...Ch. 4 - Complete the equation for the reaction between...Ch. 4 - Each of these reactions can be written as a Lewis...Ch. 4 - The sec-butyl cation can react as both a...Ch. 4 - Prob. 4.36APCh. 4 - Prob. 4.37APCh. 4 - Prob. 4.38APCh. 4 - Explain why the hydronium ion, H3O+, is the...Ch. 4 - What is the strongest base that can exist in...Ch. 4 - Prob. 4.42APCh. 4 - Prob. 4.43APCh. 4 - Methyl isocyanate, CH3N=C=O, is used in the...Ch. 4 - Offer an explanation for the following...Ch. 4 - Prob. 4.46APCh. 4 - Alcohols (Chapter 10) are weak organic acids, pKa...Ch. 4 - As we shall see in Chapter 19, hydrogens on a...Ch. 4 - 2,4-Pentanedione is a considerably stronger acid...Ch. 4 - Write an equation for the acid-base reaction...Ch. 4 - Prob. 4.51APCh. 4 - Prob. 4.52APCh. 4 - Prob. 4.53APCh. 4 - Following is a structural formula for imidazole, a...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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_forwardDefine or illustrate the meaning of the following terms: a. Ka reaction b. Ka equilibrium constant c. Kb reaction d. Kb equilibrium constant e. conjugate acidbase pairarrow_forwardPhenol, C6H5OH, has a Ka of 1.3 x10-10.(a) Write out the Ka reaction for phenol.(b) Calculate Kb for phenol’s conjugate base.(c) Is phenol a stronger or weaker acid than water?arrow_forward
- Consider two acids: HCO2H (formic acid, pKa = 3.8) and pivalic acid [(CH3)3CCO2H, pKa = 5.0]. (a) Which acid has the larger Ka? (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?arrow_forwardWhich, 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_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
- For each value of Ka, calculate the corresponding value of pKa. Which compound is the stronger acid? Q.) chloroacetic acid, Ka = 1.38 X 10-3arrow_forward6. Draw two graphs for weak acid HA: (a) percent dissociation for HA versus the initial concentration of HA ([HA]o) (hint: assume [HA], as x and [H*]/[HA], as y). (b) the equilibrium concentration of H+ versus [HA]o. Explain both.arrow_forwardEphedrine (C10H15ON) is a base that is used in nasalsprays as a decongestant.(a) Write an equation for its equilibrium reaction with water.(b) The Kb for ephedrine is 1.4 × 10-4 . Calculate the Ka for its conjugate acid.(c) Is ephedrine a weaker or a stronger base than ammonia?arrow_forward
- + 2) HA is a weak acid. HA is dissociated to H and A in water. At equilibria, if the pH of the solution is 3.24, then what is the concentration of A. [A [H*] At what condition, pH = pka? 3) pH = pKa + logarrow_forwardAmmonia, NH 3, is amphoteric. (a) Draw the conjugate acid of NH 3. (b) Draw the conjugate base of NH 3.arrow_forwardThe Ka of a weak acid is 3.33 x 10-5, what is the pKb of it's conjugate base?arrow_forward
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