Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Textbook Question
Chapter 2, Problem 2.39SP
The Ka of phenylacetic acid is 5 2 × 10−5, and the pKa of propionic acid is 4 87.
- a. Calculate the pKa of phenylacetic acid and the Ka of propionic acid.
- b. Which of these is the stronger acid? Calculate how much stronger an acid it is.
- c. Predict whether the following equilibrium will favor the reactants or the products.
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Students have asked these similar questions
For the following reaction:
OH
NH
a-Label the acid and base in the starting materials.
b-Draw the conjugate acid and conjugate base.
c-Label the conjugate acid and conjugate base.
d-Give the approximate pka of the acid and conjugate acid.
e-State whether the reaction will proceed more toward reactants or toward products.
Which 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.
Which acid do you think would have the lower pKa value: HBrO4, HBrO3, HBrO2, or HBrO? Explain your answer.
Chapter 2 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Ch. 2.1A - Prob. 2.1PCh. 2.1B - The NF bond is more polar than the NH bond: but...Ch. 2.1B - For each of the following compounds 1. Draw the...Ch. 2.1B - Two isomers of 1,2-dichloroethene are known One...Ch. 2.2C - Prob. 2.5PCh. 2.2C - Prob. 2.6PCh. 2.3 - Prob. 2.7PCh. 2.4 - Calculate the pH of the following solutions a....Ch. 2.6A - Ammonia appears in Table 2-2 as both an acid and a...Ch. 2.7 - Write equations for the following acid-base...
Ch. 2.7 - Ethanol, methylamine. and acetic acid are all...Ch. 2.8 - Prob. 2.12PCh. 2.10 - Write equations for the following acid-base...Ch. 2.10 - Rank the following acids in decreasing order of...Ch. 2.11 - Prob. 2.15PCh. 2.11 - Prob. 2.16PCh. 2.11 - Consider each pair of bases and explain which one...Ch. 2.12 - Which is a stronger base ethoxide ion or acetate...Ch. 2.12 - Prob. 2.19PCh. 2.12 - Prob. 2.20PCh. 2.12 - Prob. 2.21PCh. 2.12 - Choose the more basic member of each pair of...Ch. 2.14 - Prob. 2.23PCh. 2.15D - Classify the following hydrocarbons and draw a...Ch. 2.16D - Prob. 2.25PCh. 2.17C - Draw a Lewis structure and classify each of the...Ch. 2.17C - Circle the functional groups in the following...Ch. 2 - The CN triple bond in acetonitrile has a dipole...Ch. 2 - Prob. 2.29SPCh. 2 - Sulfur dioxide has a dipole moment of 1.60 D....Ch. 2 - Which of the following pure compounds can form...Ch. 2 - Predict which member of each pair is more soluble...Ch. 2 - Prob. 2.33SPCh. 2 - Prob. 2.34SPCh. 2 - Predict which compound in each pair has the higher...Ch. 2 - All of the following compounds can react as acids...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - The Ka of phenylacetic acid is 5 2 105, and the...Ch. 2 - The following compound can become protonated on...Ch. 2 - The following compounds are listed in increasing...Ch. 2 - Prob. 2.42SPCh. 2 - Prob. 2.43SPCh. 2 - Compare the relative acidity of 1-molar aqueous...Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - The following compounds can all react as bases. a....Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - Prob. 2.48SPCh. 2 - Methyllithium (CH3Li) is often used as a base in...Ch. 2 - Label the reactants in these acid-base reactions...Ch. 2 - In each reaction, label the reactants as Lewis...Ch. 2 - Prob. 2.52SPCh. 2 - Each of these compounds can react as a nucleophile...Ch. 2 - Prob. 2.54SPCh. 2 - Give a definition and an example for each class of...Ch. 2 - Circle the functional groups in the following...Ch. 2 - Prob. 2.57SP
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- Which has the larger numerical value? (a) The pKa of a strong acid or the pKa of a weak acid (b) The Ka of a strong acid or the Ka of a weak acidarrow_forwardWill acetylene react with sodium hydride according to the following equation to form a salt and hydrogen, H2? Using pKa values given in Table 4.1, calculate Keq for this equilibrium.arrow_forwardCalculate the pH of an acetic acid solution, originally 0.25 M, in water. The pKa for acetic acid = 4.76.arrow_forward
- Benozic acid (C6H5COOH) has a pKa of 4.20. a. What is the ratio of the acid to its conjugate base at a pH of 2.20?arrow_forwardA 0.480 M solution is made with the compound shown below. I. What class of acid or base is this compound? O Carboxylic acid O Conjugate of a carboxylic acid ○ Oxyacid O Conjugate base of an oxyacid O Amine O Conjugate acid of an amine II. What would be the pH of this solution if the acid form has a pKa = 5.15arrow_forwardFor each value of pKa, calculate the corresponding value of Ka. Which compound is the stronger acid? Q.) carbonic acid, pKa = 6.36arrow_forward
- Fumaric acid and malonic acid are both diprotic acids. a. Sketch the general shape of the curve for a diprotic acid with Ka1 >> Ka2. Explain how to determine pKa1, pKa2, and the molecular weight. b. Sketch the general shape of the curve for a diprotic acid with Ka1 ≈ Ka2. c. Sketch the general shape of a curve for a triprotic acid with Ka1 >> Ka2 >> Ka3.arrow_forwardThe conjugate base of benzoic acid is used as a 72 preservative. Write the equilibrium reaction for this weak acid in aqueous solution. ОН Benzoic acid a. What substances are present at equilibrium? b. At equilibrium, are reactants or products favored, and why? c. Are the concentrations of benzoic acid and benzoate constant or changing at equilibrium? d. What happens to the equilibrium if more hydronium ions are added to the reaction? e. Label the conjugate acid-base pairs.arrow_forwardWhich of the following is true about acids and bases? A. When bases ionize, they donate protons. B. Strong acids and bases are completely ionized in dilute aqueous solutions. C. The dissociation constant of a strong acid is lower than that for a weak acid. D. The pKa of a strong acid will be higher than that for a weak acid.arrow_forward
- The benzylammonium ion (c6H5CH2NH3+) has pka=9.33 and the propylammonium ion has pka=10.71. Which is the stronger base, benzylamine or propylaminearrow_forwardThe pka of butanoic acid is 4.82. butanoic acid a. Draw the structure that predominates at a pH of 1.50. b. Draw the structure that predominates at a pH of 9.40. c. Calculate the ratio of conjugate base to acid at a pH of 1.50 d. Calculate the ratio of conjugate base to acid at a pH of 9.40.arrow_forward
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