Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 20, Problem 20.44AP
Interpretation Introduction
Interpretation:
Among the fluids, stomach acid or the bloodstream, the one in which penicillin-G is more soluble is to be identified.
Concept introduction:
The solubility of two substances dependents on the “like dissolves like” principle that means polar substances dissolve in polar solvents and non-polar substances will dissolve in non-polar solvents. The water-soluble compounds are hydrophilic and water-insoluble compounds are hydrophobic.
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Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
Write the products of the reaction of diphenhydramine (a base) with the acid HCl shown below. Are the reactants or products more soluble in water? Briefly explain.
Draw the structures of aspirin, caffeine, and acetaminophen. Give the hybridization of each carbon atom and state which is acidic, weakly acidic, and basic. Identify the sites on each compound that make each acidic, weakly acidic, and basic.
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 20.1PCh. 20 - Prob. 20.2PCh. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Prob. 20.5PCh. 20 - Prob. 20.6PCh. 20 - Prob. 20.7PCh. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Prob. 20.11PCh. 20 - Prob. 20.12PCh. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Prob. 20.16PCh. 20 - Prob. 20.17PCh. 20 - Prob. 20.18PCh. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Prob. 20.24PCh. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27APCh. 20 - Prob. 20.28APCh. 20 - Prob. 20.29APCh. 20 - Prob. 20.30APCh. 20 - Prob. 20.31APCh. 20 - Prob. 20.32APCh. 20 - Prob. 20.33APCh. 20 - Prob. 20.34APCh. 20 - Prob. 20.35APCh. 20 - Prob. 20.36APCh. 20 - Prob. 20.37APCh. 20 - Prob. 20.38APCh. 20 - Prob. 20.39APCh. 20 - Prob. 20.40APCh. 20 - Prob. 20.41APCh. 20 - Prob. 20.42APCh. 20 - Prob. 20.43APCh. 20 - Prob. 20.44APCh. 20 - Prob. 20.45APCh. 20 - Prob. 20.46APCh. 20 - Prob. 20.47APCh. 20 - Prob. 20.48APCh. 20 - Prob. 20.49APCh. 20 - Prob. 20.50APCh. 20 - Prob. 20.51APCh. 20 - Prob. 20.52APCh. 20 - Prob. 20.53APCh. 20 - Prob. 20.54APCh. 20 - Prob. 20.55APCh. 20 - Prob. 20.56APCh. 20 - Prob. 20.57APCh. 20 - Prob. 20.58APCh. 20 - Prob. 20.59APCh. 20 - Prob. 20.60AP
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- 8 (Chemical Connections 19C) Once it has been opened, and particularly if it has been left open to the air, a bottle of aspirin may develop a vinegar-like odor. Explain how this might happen.arrow_forwardPenicillin G has a pH of 5.0 to 7.5 pKa of 2.72 The pH is higher than the pKa of 2.72, meaning penicillin G is deprotonated. What will the carboxylic acid group will be _____ and the amine groups will be ___ and ____? Draw the structure showing those changes, then you could draw the deprotonated form.arrow_forwardComplete the equation to show how pyridine, C, H, N, acts as a Brønsted-Lowry base in water. equation: C₂H₂N+H₂O=arrow_forward
- Write the products of the reaction of diphenhydramine (a base) with the acid HCI shown below. H COCH₂CH₂NCH3 + HC1 CH3 Consider the chemical reaction from the previous question. Are the reactants or products more soluble in water? Briefly explain.arrow_forwardPlace the binders below in descending order of acidity (pi) and justify your choice: CH3CN; (C2H5)2O; PCl3; As(C6H5)3; (C2H5)3Narrow_forwardDetermine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
- Compounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes.arrow_forwardWhat is true regarding protein backbones? The protein backbone is different for each protein and contains both amine and carboxylic acid functional groups The protein backbone is the same for each protein and contains both amine and carboxylic acid functional groups The protein backbone is different for each protein and contains amide functional groups The protein backbone is the same for each protein and contains amide functional groupsarrow_forwardComplete the equation to show how pyridine, C5H5N, acts as a Brønsted-Lowry base in water. equation: C5H5N + H2Oarrow_forward
- 2. Below is the structure of caffeine. Circle and label (a) an amide functional group, (b) a tertiary amine, and (c) the purine ring system. O CH3 N CH-N O N CH3 N H 3. Caffeine is an alkaloid and has base characteristics. Of the four nitrogens in the structure of the molecule, which one(s) would give it this property? sneltro bem 4. Besides caffeine, what else is extracted into the tea? Why can you use the basic salt, Na₂CO3, sodium carbonate, to remove this material? 5. What criterion is used for the purity of a sample of caffeine?arrow_forwardWrite the chemical equation for the acid dissociation of acetaminophen, C8H9O2N. Write the Ka expression for the acid dissociation of acetaminophen.arrow_forwardExplain why CH3 CH2 CH2NH2 is a Brønsted base. Its water solutions are basic. All substances containing nitrogen atoms are Brønsted bases. This amine is a proton donor. This amine can ассеpt a proton from a proton donor.arrow_forward
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