Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 20.2, Problem 4P
The Ka for dichloroacetic acid is 3.32 Ă— 10-2. Approximately what percentage of the acid is dissociated in a 0.10 M aqueous solution?
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Write the values of Y and X.
H2SO4
CH3CH=CH2 + H2O
CH;CH-CH2
H HỌ
2-propanol
an alcohol
The pKa of a protonated alcohol is about -2.5, and the pKa of an alcohol is about 15.
Therefore, as long as the pH of the solution is greater than Y and less than X, more than
50% of 2-propanol will be in its neutral, nonprotonated form.
Express your answers using two significant figures separated by a comma.
AX中
Y, X =
%3|
2) Calculate the pH of a sólution prepared by dissolving 0.150 mol of acetic acid and 0.300 mol of sodium acetate in water sufficient to yield 1.00 L of solution. The Ka of acetic acid is 1.76E-5.
Calculate the pH and fraction of dissociation (a) for each of the acetic acid (CH3 COOH, pK₁ = 4.756) solutions.
A 0.00325 M solution of CH₂COOH.
pH =
3.62
α =
0.0735
Incorrect
Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Give IUPAC names for the following compounds:Ch. 20.1 - Draw structures corresponding to the following...Ch. 20.2 - Prob. 3PCh. 20.2 - The Ka for dichloroacetic acid is 3.32 Ă— 10-2....Ch. 20.3 - Calculate the percentages of dissociated and...Ch. 20.4 - Which would you expect to be a stronger acid, the...Ch. 20.4 - Dicarboxylic acids have two dissociation...Ch. 20.4 - The pKa of p-cyclopropylbenzoic acid is 4.45. Is...Ch. 20.4 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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- HO. COOH 7. (7a) + 2 NaOH _(7b) + NazCOa. +. H2Oarrow_forwardNaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forwardIn which one of the following solutions will acetic acid have the greatest percent ionization? K₂ = 1.8 x 10-5 0.10 M CH3COOH plus 0.10 M CH3COONa 0.10 M CH3COOH plus 0.20 M CH3COONa 0.10 M CH3COOH O 0.10 M CH3COOH dissolved in 1.0 M HCIarrow_forward
- The Ka of CH3COOH is 1.8 x 10-5. Calculate the pH of a solution containing both 0.20 M CH3COOH and 0.30 M CH3COONa.arrow_forwardThe pH of a 0.12 M solution of acetic acid (HCH3CO2) is measured to be 2.83. Calculate the acid dissociation contant Ka of acetic acid.arrow_forwardCalculate the percent dissociation of trimethylacetic acid (C,H,CO,H) in a 0.15 mM aqueous solution of the stuff.arrow_forward
- 1) When starting with completely un-dissociated acetic acid, is it accurate to assume that [HOAc]0 = [HOAc]eq? Why or why not? 2) A highly concentrated acetic acid solution contains 15.0 M acetic acid at equilibrium. What are the equilibrium concentrations of the hydronium and acetate ions in this solution?arrow_forwardWhat is the pH of an aqueous solution containing 0.50 mol L–1 ethanoic acid, 0.30 mol L–1 sodium ethanoate, and 0.10 mol L–1 HCl? [The pKa of ethanoic acid is 4.75.]arrow_forward2,4-Pentanedione is a considerably stronger acid than is acetone (Chapter 19). Write a structural formula for the conjugate base of each acid and account for the greater stability of the conjugate base from 2,4-pentanedione.arrow_forward
- Answer the following statement. Provide an explanation. What happens to compound X when ph=pkb ph>pkb pharrow_forwardC6H5NH2 + H2O <-> C6H5NH3+ + OH-. Aniline, a weak base, reacts with water according to the reaction. (a) a sample of aniline is dissolved in water to produce 25.0 mL of 0.10 m solution. The pH of the solution 8.82. Calculate the equilibrium constant, Kb, for this reaction (b) What is the percent disassociation for the solution in part (a) (c) 25.0 mL of 0.10 HCI was then added in a titration experiment. What is the pH at the equivalence point?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_forward
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