Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 3, Problem 31P
(a) The
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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
Identify the Lewis acid and Lewis base in each equation:
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…
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
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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
- Consider these acids (a) Arrange the acids in order of increasing acid strength from weakest to strongest. (b) Which acid has the smallest pKa value?arrow_forwardThe pH of a 0.10-M solution of propanoic acid, CH3CH2COOH, a weak organic acid, is measured at equilibrium and found to be 2.93 at 25 °C. Calculate the Ka of propanoic acid.arrow_forwardFor 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_forward
- Which acid has the strongest conjugate base? (a) HNO2 (b) C6H5CO2H (c) HCN (d) HClarrow_forwardWhich 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_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_forward
- Calculate the pKa value for each of the following acids. a. Nitrous acid (HNO2), Ka = 4.5 104 b. Carbonic acid (H2CO3), Ka = 4.3 107 c. Dihydrogen phosphate ion (H2PO4), Ka = 6.2 108 d. Sulfurous acid (H2SO3), Ka = 1.5 102arrow_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_forwardFor each value of Ka, calculate the corresponding value of pKa. Which compound is the stronger acid? (a) Acetic add, Ka = 1.74 105 (b) Chloroacetic acid, Ka= 1.38 103arrow_forward
- Calculate Ka for the weak acids that have the following PKa values. (a) 3.9(b) 10.12 (c) 13.07arrow_forwardFind the value of Kb for the conjugate base of the following organic acids. (a) picric acid used in the manufacture of explosives; K a =0.16 (b) trichloroacetic acid used in the treatment of warts; K a =0.20arrow_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
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