Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 3, Problem 37P
Malonic acid, HO2CCH2CO2H, is a diprotic acid. The pKa for the loss of the first proton is 2.83; the pKa for the loss of the second proton is 5.69. (a) Explain why malonic acid is a stronger acid than acetic acid ( pKa=4.75). (b) Explain why the anion, −O2CCH2CO2H, is so much less acidic than malonic acid itself.
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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 - Prob. 15PPCh. 3 - Prob. 16PPCh. 3 - Prob. 17PPCh. 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 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - When methyl alcohol is treated with NaH, the...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. 30PCh. 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. 34PCh. 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. 42PCh. 3 - Prob. 43PCh. 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. 4LGPCh. 3 - Prob. 1QCh. 3 - Which of the following is the strongest base? (a)...Ch. 3 - Prob. 3QCh. 3 - Prob. 4QCh. 3 - Prob. 5QCh. 3 - Which would be the weakest base? (a) CH3CO2Na (b)...Ch. 3 - What acid-base reaction (if any) would occur when...Ch. 3 - The pKa of CH3NH3+ equals 10.6; the pKa of...Ch. 3 - 3.9 Supply the missing reagents.
Ch. 3 - 3.10 Supply the missing intermediates and...
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