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Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Textbook Question
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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Students have asked these similar questions
(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-.
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 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
- Define 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_forwardConsider 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_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
- 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_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_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_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_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_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
- Ammonia, 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_forward4. 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.arrow_forward
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