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

Acid Base Equilibrium

Organic Chemistry

3. Acids and Bases

Acid Base Equilibrium

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6:41 minutes

Problem 1b

Textbook Question

Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.

Verified step by step guidance

Step 1: Identify the acids and conjugate bases in each reaction. For example, in the first reaction, NH3 is the acid and NH2Li is the conjugate base. Similarly, analyze the acids and bases for the other reactions.

Step 2: Use the pKa values from Appendix I to determine the relative acidity of the acids involved in each reaction. Recall that a lower pKa value indicates a stronger acid.

Step 3: Compare the pKa values of the acids on both sides of the equilibrium for each reaction. The equilibrium will favor the formation of the weaker acid (higher pKa value).

Step 4: For each reaction, determine whether the equilibrium favors the products or the reactants based on the pKa comparison. For example, if the acid on the product side has a higher pKa than the acid on the reactant side, the equilibrium favors the products.

Step 5: Summarize the findings for all three reactions, indicating which reactions favor product formation and which do not, based on the pKa values and the principle that equilibrium favors the weaker acid.

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Key Concepts

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

Acid-Base Equilibrium

In acid-base reactions, the equilibrium favors the formation of the weaker acid and the weaker base. This principle is crucial for predicting the direction of the reaction. The strength of acids and bases can be compared using their pKa values, where a higher pKa indicates a weaker acid. Understanding this concept helps in determining which products are favored in the given reactions.

pKa Values

pKa values are a quantitative measure of the strength of an acid in solution. The lower the pKa, the stronger the acid, and conversely, a higher pKa indicates a weaker acid. In the context of the reactions provided, knowing the pKa values of the acids involved allows for the prediction of which side of the equilibrium will be favored based on the relative strengths of the acids and bases formed.

Grignard Reagents

Grignard reagents, such as CH3MgBr, are highly reactive organomagnesium compounds that act as nucleophiles in organic reactions. They can react with various electrophiles, including carbonyls and acids. In the context of the question, understanding how Grignard reagents interact with amines and other compounds is essential for predicting the products and the direction of the equilibrium in the reactions presented.

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Related Practice

Textbook Question

Predict the products of the following acid–base reactions, or indicate if no significant reaction would take place.

a. H—C≡C—H + NaNH₂

b. H—C≡C—H + CH₃Li

c. H—C≡C—H + NaOCH₃

Textbook Question

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(e) (CH₃)₃C–O^– + CH₃CH₂OH ⇌

Textbook Question

Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.

(d)

Textbook Question

Would amide or acetate most easily deprotonate an alcohol to make the alkoxide anion? Calculate K_eq for each possibility.

Textbook Question

Which of the following reactions favor formation of the products? Recall that the equilibrium favors formation of the weaker acid.

Textbook Question

The acid-catalyzed hydrolysis of an ester results in the formation of an equal amount of carboxylic acid and alcohol.

(a) Design a flow chart for separating the two products.

Textbook Question

Complete the following proposed acid–base reactions, and predict whether the reactants or products are favored.

(a)

(b)

Textbook Question

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline

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