Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 16.6, Problem 13P
Using the pKa values listed in Table 15.1, predict the products of the following reactions:
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Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - The aromas of many flowers and fruits are due to...Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.1 - Prob. 4PCh. 16.2 - Prob. 5PCh. 16.2 - Which is longer, the carbon-oxygen single bond in...Ch. 16.2 - There are three carbon-oxygen bonds in methyl...Ch. 16.2 - Prob. 8PCh. 16.4 - Prob. 9PCh. 16.4 - Prob. 10P
Ch. 16.5 - a. What is the product of the reaction of acetyl...Ch. 16.6 - a. Which compound has the stretching vibration for...Ch. 16.6 - Using the pKa values listed in Table 15.1, predict...Ch. 16.6 - Is the following statement true or false? If the...Ch. 16.7 - What is the product of an acyl substitution...Ch. 16.8 - PROBLEM 16
Starting with acetyl chloride, what...Ch. 16.8 - Prob. 18PCh. 16.9 - We saw that it is necessary to use excess amine in...Ch. 16.9 - Prob. 20PCh. 16.9 - a. state three factors that cause the uncatalyzed...Ch. 16.10 - Prob. 23PCh. 16.10 - Using the mechanism for the acid-catalyzed...Ch. 16.10 - Prob. 25PCh. 16.10 - Prob. 27PCh. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.11 - Prob. 30PCh. 16.12 - Prob. 31PCh. 16.12 - Prob. 32PCh. 16.13 - Prob. 34PCh. 16.13 - Which has a higher melting point, glyceryl...Ch. 16.13 - Draw the structure of an optically inactive fat...Ch. 16.13 - Draw the structure of an optically active fat...Ch. 16.14 - Show how each of the following esters could he...Ch. 16.14 - Prob. 39PCh. 16.15 - Prob. 40PCh. 16.15 - Which of the following reactions leads to the...Ch. 16.16 - Prob. 42PCh. 16.16 - Prob. 43PCh. 16.18 - Prob. 44PCh. 16.18 - Prob. 45PCh. 16.19 - Prob. 46PCh. 16.19 - Which alkyl halides from the carboxylic acids...Ch. 16.20 - Prob. 49PCh. 16.20 - Prob. 50PCh. 16.20 - Prob. 51PCh. 16.21 - Prob. 52PCh. 16.21 - Prob. 53PCh. 16.22 - How could you synthesize the following compounds...Ch. 16 - Prob. 55PCh. 16 - Name the following:Ch. 16 - Prob. 57PCh. 16 - What compound are obtained from the fallowing...Ch. 16 - a. Rank the following esters in order of...Ch. 16 - Because bromocyclohexane is a secondary alkyl...Ch. 16 - a. Which compound would you expect to have a...Ch. 16 - How could you use 1H NMR spectroscopy to...Ch. 16 - Prob. 63PCh. 16 - a. When a carboxylic acid is dissolved in...Ch. 16 - Rank the following compounds in order of...Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - A compound with molecular formula C5H10O2 gives...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Two products, A and B, are obtained from the...Ch. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - When treated with an equivalent of methanol,...Ch. 16 - a. Identify the two products obtained from the...Ch. 16 - Prob. 80PCh. 16 - Identity the major and minor products of the...Ch. 16 - Prob. 82PCh. 16 - When a compound with molecular formula C11H14O2...Ch. 16 - Prob. 84PCh. 16 - Prob. 85PCh. 16 - The 1H NMR spectra for two esters with molecular...Ch. 16 - Show how the following compounds could be prepared...Ch. 16 - Prob. 88PCh. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - The intermediate shown here is formed during the...Ch. 16 - Prob. 92PCh. 16 - Propose a mechanism that accounts for the...Ch. 16 - Catalytic antibodies catalyze a reaction by...Ch. 16 - Prob. 95P
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- What is the dominant form of arsenic acid (H3A) at pH =9.23 ? Given: pKa1 = 2.24 , pKa2 = 6.96, pKa3 = 11.5arrow_forwardDicarboxylic 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_forwardwhy do these compounds show this trend in pka?arrow_forward
- Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups.CH4 CH3NO2 CH2(NO2)2 CH(NO2)3 pKa ≅ 50 pKa = 10.2 pKa = 3.6 pKa = 0.17arrow_forwardThe pka of the methylammonium ion is 10.62. At what pH is methylammonia 1/5 ionized?arrow_forwardThe pKa values of the two ammonium cations drawn below are 8.33 and11.1. Which pKa corresponds to which cation? Explain your choice.?arrow_forward
- Why does methyl orange have a lower pKa value (pKa~3.5) than methyl red (pKa ~5.1)?arrow_forwardCalculate the percentage of free acid for (a) phenobarbital (it is an acid with pKa = 7.40) and (b) hexobarbital (also an acid with pKa = 8.4) at the physiological condition of pH 7.4.arrow_forwardCompare the relative acidity of 1-molar aqueous solutions of the following acids.NH4Cl CH3COOH BrCH2COOH F3CCOOH H2SO4 HCl HBrpKa = 9.26 pKa = 4.74 pKa = 2.9 pKa = 0.2 pKa = -5 pKa = -7 pKa = -9arrow_forward
- Why are the carboxylic acid groups of the amino acids more acidic (pKa - 2) than a carboxylic acid such as acetic acid (pKa = 4.76)?arrow_forwardThe normal pH range for blood plasma is 7.35–7.45. Under these conditions, would you expect the carboxyl group of lactic acid (pKa 3.08) to exist primarily as a carboxyl group or as a carboxylic anion? Explain.arrow_forwardwe use the algebra method to find the pka values of 3.954 and the graphical method to find the pKa is 3.9533, with an accepted value of 4.0 Compare your algebraically and graphically determined pK values. Which method was moreaccurate? Why would you expect these values to be very close to each other?arrow_forward
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