Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 11.4, Problem 6P
- a. What is the product of the reaction of acetyl chloride with HO−? The pKa of HCl is −7; the pKa of H2O is 15.7.
- b. What is the product of the reaction of acetamide with HO−? The pKa of NH3 is 36; the pKa of H2O is 15.7.
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a. What is the product of the reaction of acetyl chloride with HO-? The pKa of HCl is -7; the pKa of H2O is 15.7.
b. What is the product of the reaction of acetamide with HO-? The pKa of NH3 is 36; the pKa of H2O is 15.7.
A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. a. If the pKa value of a carboxylic acid such as acetic acid is about 5 (see Table 2.1), then why is the pKa value of the carboxylic acid group of alanine so much lower? b. Draw the structure of alanine in a solution at pH = 0. c. Draw the structure of alanine in a solution at physiological pH (pH 7.4). d. Draw the structure of alanine in a solution at pH = 12. e. Is there a pH at which alanine is uncharged (that is, neither group has a charge)? f. At what pH does alanine have no net charge (that is, the amount of negative charge is the same as the amount of positive charge)?
Both mepivacaine and bupivacaine are local anesthetics used in epidural blocks. Mepivacaine has a pKa of 7.6, whereas bupivacaine has a pKa of 8.1. Based on their pKa values, which of these will have more of the uncharged form available at physiological pH, thereby blocking pain quicker?
Chapter 11 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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- The pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98. a. Which carboxyl group is the stronger acid? b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.arrow_forwardWhy is the pK of the carboxyl group of glycine (pK = 2.3) less than that for acetic acid (pK = 4.76)?arrow_forwardThe pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.a. Which carboxyl group is the stronger acid?b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.arrow_forward
- A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. The pKa values of the two groups are shown.(a). If the pKa value of a carboxylic acid such as acetic acid is about 5, then why is the pKa value of the carboxylic acid group of alanine so much lower? (b). Draw the structure of alanine in a solution at pH = 0. (c). Draw the structure of alanine in a solution at physiological pH (pH 7.4).(d). Draw the structure of alanine in a solution at pH = 12. (e). Is there a pH at which alanine is uncharged (that is, neither group has a charge)? (f) At what pH does alanine have no net charge (that is, the amount of negative charge is the same as the amount of positive charge)?arrow_forwardThe pKa of salicylic acid is 2.97 whereas the pKa of benzoic acid is 4.19. Why is salycilic acid a much stronger acid compared to benzoic acid? (It is not enough to say “because the pKa is lower...”)arrow_forwardWhy does the Ka values decrease at each deprotonation in the reaction between naoh and h3po4?arrow_forward
- mention the conjugate bases and use structures to explain the following: a. why is the alpha proton of a ketone (pKa ~ 16) is more acidic than the protons in CH3CH3? b. why is the alpha proton of a ketone (pKa ~ 16) is more acidic than the protons in a ester (pKa ~ 35)? c. why are the hydrogens in a C-H bond like CH3CH3 difficult to remove?arrow_forwardConsider the properties of sodium carbonate (Na2CO3), potassium carbonate (K2CO3), andsodium hydroxide (NaOH). How do they differ by pKa? Nucleophilicity? Solubility?arrow_forwardThe pKa of acetic acid in water is 4.76. What effect will a decrease in the polarity of the solvent have on the pKa? Why?arrow_forward
- Lactic acid (HC3H5O3) has one acidic hydrogen. A 0.10 M solution of lactic acid has a pH of 2.44 Calculate the pKa at 25°C. Report your answer to the hundredths placearrow_forwardWhich of the compounds have the lowest pKA, why?arrow_forward(a) Write the chemical equation for the reaction involved in Cannizzaro reaction.(b) Draw the structure of the semicarbazone of ethanal.(c) Why pKa of F—CH2—COOH is lower than that of Cl—CH2—COOH?arrow_forward
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