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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3:28 minutes

Problem 20a

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.

Verified step by step guidance

Step 1: Analyze the reaction products. The acid-catalyzed hydrolysis of the ester results in two products: a carboxylic acid (benzoic acid derivative) and an alcohol (cyclopentylmethanol). These compounds have different chemical properties that can be exploited for separation.

Step 2: Use acid-base extraction to separate the carboxylic acid and alcohol. Dissolve the reaction mixture in a non-polar organic solvent (e.g., diethyl ether) and add an aqueous solution of a base, such as sodium hydroxide (NaOH). The carboxylic acid will react with the base to form a water-soluble carboxylate salt, while the alcohol remains in the organic layer.

Step 3: Separate the layers using a separatory funnel. The aqueous layer will contain the carboxylate salt, and the organic layer will contain the alcohol. Carefully drain the aqueous layer and collect the organic layer.

Step 4: Recover the carboxylic acid by acidifying the aqueous layer. Add a strong acid, such as hydrochloric acid (HCl), to the aqueous layer to convert the carboxylate salt back into the carboxylic acid. The carboxylic acid will precipitate or can be extracted into an organic solvent.

Step 5: Purify the alcohol and carboxylic acid. The alcohol can be purified by distillation or recrystallization, depending on its physical properties. The carboxylic acid can be purified by recrystallization or extraction into a fresh organic solvent followed by evaporation.

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Key Concepts

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

Acid-Catalyzed Hydrolysis

Acid-catalyzed hydrolysis is a chemical reaction where an ester reacts with water in the presence of an acid catalyst, typically a strong acid like sulfuric acid. This process breaks the ester bond, resulting in the formation of a carboxylic acid and an alcohol. Understanding this reaction is crucial for predicting the products and their separation methods.

Separation Techniques

Separation techniques are methods used to isolate and purify the products formed in a chemical reaction. In the case of the acid-catalyzed hydrolysis of an ester, techniques such as distillation, extraction, or chromatography can be employed to separate the carboxylic acid from the alcohol. Knowledge of these techniques is essential for designing an effective flow chart for product separation.

Chemical Equilibrium

Chemical equilibrium refers to the state in a reversible reaction where the rates of the forward and reverse reactions are equal, resulting in constant concentrations of reactants and products. In the context of ester hydrolysis, understanding equilibrium helps in predicting the yield of carboxylic acid and alcohol, which is important for optimizing separation processes.

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Related Practice

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

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

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

Textbook Question

Phenols are less acidic than carboxylic acids, with values of pK_a around 10. Phenols are deprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three pure compounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.

Textbook Question

For the following acid–base pairs, (iii) predict the favored side of equilibrium;

(e)

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