Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 20.SE, Problem 40AP
Thioglycolic acid, HSCH2CO2H, a substance used in depilatory agents (hair removers) has pKa = 3.42. What is the percent dissociation of thioglycolic acid in a buffer solution at pH = 3.0?
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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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- Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a monoanion and one for the second dissociation into a dianion. For oxalic acid, HO2C—CO2H, the first ionization constant is pKal = 1.2 and the second ionization constant is pKa2 = 4.2. Why is the second carboxyl group far less acidic than the first?arrow_forwardPhenylacetic acid (C6H5CH2COOH, simplified here to HPAc is a monoprotic acid. It builds up in the blood of persons with phenylketonuria, that if untreated, causes mental retardation and death. A study of the acid shows that the pH of 0.120 M HPAc is 2.62. What are (a) the Ka and (b) pKa of phenylacetic acid?arrow_forwardCalculate the pKa of the weak acid HA, given that a solution of 0.65 M HA and 0.85 M NaA has a pH of 4.75arrow_forward
- The pKa of a particular weak acid is 4.85. What is the pH of the weak acid solution when exactly half of the acid is neutralized?arrow_forwardConsider a diprotic acid with pKa values of 1.60 and 4.50, that is colorless when fully protonated, deep blue when singly deprotonated, and bright red when doubly deprotonated. Assuming that both colored forms have large and approximately equal molar absorptivities, what can be inferred from a solution of the compound that has a faint blue color?arrow_forwardEstimate the pH and percentage of dissociation of 0.010 M CH3CH(OH)COOH(aq) (lactic acid). pKa of lactic acid is 3.86.arrow_forward
- How many grams of sodium formate, NaCHO2 need to be dissolved in 119 mL of a 0.86 M formic acid (CHO2H, pKa=3.75) solution so that the [CHO2–]=[CHO2H]?arrow_forwardIf the Ka of the conjugate acid is 4.39 × 10-8 , what is the pKb for the base?arrow_forwardThe Ka of a weak acid is 3 x 10^-12 What is the pKa of this acid?arrow_forward
- What 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_forwardWhat is the pH of 500mL of a buffer solution of HC3H5O3 0.0570M and C3H5O3Na 0.0275M? Ka of HC3H5O3 = 1.9x10^-5arrow_forwardTrichloroacetic acid (CCl3COOH) is a corrosive acid that is used to precipitate proteins. The pH of a 0.050 M solution of trichloroacetic acid is the same as the pH of a 0.040 M HClO4 solution. Calculate Ka and pKa for trichloroacetic acid.arrow_forward
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