Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
9th Edition
ISBN: 9781305780170
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 20.4, Problem 7P
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?
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Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.
Identify the acid and conjugate base in each reaction. Calculate the pKA for each acid. List them in order from the strongest to weakest acid. The acid-ionization constants, KA, at 25°C are provided for each.
C6H5OH + H2O Û H3O+ + C6H5O-, KA = 1.2589254 x 10-10
CH3CO2H + H2O Û H3O+ CH3CO2-, KA = 1.5848 x 10-5
CF6CO2H+H2O Û H3O+ + CF6CO2-, KA = 0.6309
1. Write the equilibrium-constant expressions and obtain numerical values for each constant in(a) the basic dissociation of aniline, C6H5NH2 .(b) the acidic dissociation of hypochlorous acid, HClO.(c) the acidic dissociation of methyl ammonium hydrochloride, CH3NH3Cl.(d) the basic dissociation of NaNO2 .(e) the dissociation of H3AsO3 to H3O + and AsO33-
2. The chemicals A and B react as follows to produce C and D:
A + B ↔ C + DKe = [C] [D] [A] [B]
The equilibrium constant Ke has a value of 0.30. Assume 0.20 mol of A and 0.50 mol of B are dissolved in 1.00 L, and the reaction proceeds. Calculate the concentrations of reactants [A], [B] and products [C], [D] at equilibrium.
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Chapter 20 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
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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