Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

3. Acids and Bases

Ranking Acidity

Organic Chemistry

3. Acids and Bases

Ranking Acidity

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2:48 minutes

Problem 77

Textbook Question

Consider the following drugs used to treat the indicated diseases. Would you expect the activity of these drugs to be impacted by a patient taking other medicines for acid reflux disease?

Verified step by step guidance

Step 1: Analyze the chemical structures of the drugs provided in the image. Lovastatin, Vyvanse, Viagra, Tarceva, and aspirin all have functional groups that could be impacted by changes in pH or enzymatic activity in the stomach or liver.

Step 2: Consider the mechanism of action for acid reflux medications. These drugs often work by reducing stomach acid production, which can alter the pH of the stomach and potentially impact the solubility and absorption of other drugs.

Step 3: Evaluate the functional groups in each drug. For example, lovastatin contains ester groups that may undergo hydrolysis, Vyvanse has an amide bond, Viagra has sulfonamide and aromatic groups, Tarceva has ether and amide groups, and aspirin contains a carboxylic acid group. The activity of these functional groups can be influenced by pH changes.

Step 4: Consider the role of enzymes such as cytochrome P450 in drug metabolism. Acid reflux medications can inhibit or induce these enzymes, which may alter the metabolism of the drugs listed. For instance, lovastatin is metabolized by CYP3A4, and its activity could be impacted by enzyme inhibition.

Step 5: Conclude that the activity of these drugs could be impacted by acid reflux medications due to changes in pH affecting drug solubility and absorption, as well as potential interactions with enzymes involved in drug metabolism. Further investigation into specific drug-drug interactions would be necessary to confirm the extent of the impact.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Drug Interactions

Drug interactions occur when the effects of one drug are altered by the presence of another drug. This can lead to increased toxicity, reduced efficacy, or unexpected side effects. Understanding how different medications interact is crucial for patient safety, especially when multiple drugs are prescribed simultaneously.

Acid-Base Chemistry

Acid-base chemistry is fundamental in organic chemistry, particularly in how drugs are absorbed and metabolized in the body. Many drugs are weak acids or bases, and their solubility and absorption can be significantly affected by the pH of the environment, such as the stomach or intestines, which can be altered by medications for acid reflux.

Pharmacokinetics

Pharmacokinetics refers to the study of how drugs move through the body, including absorption, distribution, metabolism, and excretion. Changes in pharmacokinetics due to other medications can affect the concentration of a drug in the bloodstream, potentially leading to therapeutic failure or increased side effects, especially in patients taking multiple medications.

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Related Practice

Textbook Question

Identify the most acidic proton in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer. [Always start by drawing the conjugate base.]

(d)

Textbook Question

Which acid in each pair would you expect to more readily donate a proton to a basic compound?

(a)

Textbook Question

Why is the pK_a value of protonated hydroxylamine (6.0) so much lower than the value of a protonated primary amine such as protonated methylamine (10.7)?

Textbook Question

In light of your answers to Assessments 24.54 and 24.55, rank the following based on the rate of protonation of the alkene (1 = most basic, 6 = least basic). [Ignore the fact that the alkene may not be the most basic site in the molecule.]

Textbook Question

Which is the most stable base in each pair?

Textbook Question

Explain why a base can remove a proton from the α-carbon of N,N-dimethylethanamide but not from the α-carbon of either N-methylethanamide or ethanamide.

Textbook Question

Citrus fruits are rich in citric acid, a compound with three COOH groups. Explain the following:

a. The first pK_a (for the COOH group in the center of the molecule) is lower than the pK_a of acetic acid.

Textbook Question

Which of the following amino acid side chains can help remove a proton from the α-carbon of an aldehyde?

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