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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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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For each value of Ka, calculate the corresponding value of pKa. Which compound is the stronger acid?
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+
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
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At what condition, pH = pka?
3) pH = pKa + log
The Ka of a weak acid is 3.33 x 10-5, what is the pKb of it's conjugate base?
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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- 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_forward3. For each of the following pairs of ions, identify the stronger base: (a) OH or NHz (b) F or Ch (c) CHSCH2O or CHSCOO Answer:arrow_forward
- 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…arrow_forwardWhich of the following has the strongest conjugate base? Group of answer choices benzoic acid (Ka = 6.5 x 10-5) hydrazoic acid (Ka = 1.9 x 10-5) chlorous acid (Ka = 1.1 x 10-2) carbonic acid (Ka = 4.3 x 10-7) chloroacetic acid (Ka = 1.4 x 10-3)arrow_forwardHydroxide (-OH) can react as a Brønsted–Lowry base (and remove a proton), or a Lewis base (and attack a carbon atom). (a) What organic product is formed when -OH reacts with the carbocation (CH3)3C+ as a Brønsted–Lowry base? (b) What organic product is formed when -OH reacts with (CH3)3C+ as a Lewis base?arrow_forward
- (4) Which acid below would have a stronger conjugate base? Give the reason (a) HCN, Ka 6.2 x 10-10 Ka=2.3 x 10-⁹ (b) HBrO,arrow_forward3. For the following acid - base reaction, (a) predict the products; (b) identify the Bronsted acid, Bronsted base, conjugate acid, and conjugate base; (c) use curved arrows to show the flow of electron pairs in the reaction. CH3 CH2C-OH + NaNHaarrow_forwardAcetic acid (pKa = 4.75) is contained in vinegar. What is the pKb of the conjugate base of acetic acid, the acetate anion?arrow_forward
- Calculate the pH of an acetic acid solution, originally 0.25 M, in water. The pKa for acetic acid = 4.76.arrow_forwardConsider a buffered solution containing CH³NH3Cl and CH3NH₂. Which of the following statements concerning this solution are TRUE? (Ka (CH3NH3†) = 2.0 × 10-¹¹) (A) A solution consisting of 0.10 M CH3NH3Cl and 0.10 M CH3NH₂ would have a higher buffering capacity than one containing 1.0 M CH3NH3Cl and 1.0 M CH3NH₂. (B) If [CH3NH₂] > [CH3NH3*], then the pH is larger than the pKa value of CH3NH3*. (C) Adding more [CH3NH3Cl] to the initial buffer solution will increase the pH. (D) If [CH3NH₂] > [CH3NH3*], then pH > 10.50. (E) If [CH3NH₂] = [CH3NH3*], then pH = 3.30.arrow_forward(a) Papaverine hydrochloride is an alkaloid drug used as a muscle relaxant, particularly for acute myocardial infarctions and angina It is a weak acid. If a 0.205 M solution of papaverine hydrochloride has a pH of 3.31, what is its Ka?arrow_forward
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