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

22. Carboxylic Acid Derivatives: NAS

Fischer Esterification

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Fischer Esterification

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5:25 minutes

Problem 15c

Textbook Question

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.
(c) ethyl phenylacetate

Verified step by step guidance

Step 1: Understand the Fischer esterification process. Fischer esterification is a reaction between a carboxylic acid and an alcohol in the presence of an acid catalyst (commonly sulfuric acid) to form an ester and water. The reaction is reversible, so methods to drive the reaction to completion are important.

Step 2: Identify the reactants needed to form ethyl phenylacetate. Ethyl phenylacetate is an ester, so the carboxylic acid component is phenylacetic acid (C₆H₅CH₂COOH), and the alcohol component is ethanol (C₂H₅OH).

Step 3: Write the chemical equation for the reaction. The reaction can be represented as:

C 6 H 5 CH 2 COOH + C 2 H 5 OH \to C 6 H 5 CH 2 COO C 2 H 5 + H 2 O

. Sulfuric acid is used as a catalyst.

Step 4: Suggest a method to drive the reaction to completion. Since Fischer esterification is reversible, removing one of the products (water) can shift the equilibrium toward the formation of the ester. This can be achieved by using a Dean-Stark apparatus to continuously remove water during the reaction or by adding a drying agent to absorb water.

Step 5: Optimize reaction conditions. Use an excess of ethanol to further drive the equilibrium toward the ester product. Additionally, ensure the reaction is performed under reflux to maintain a consistent temperature and allow the reaction to proceed efficiently.

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Key Concepts

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

Fischer Esterification

Fischer esterification is a chemical reaction that forms an ester from a carboxylic acid and an alcohol in the presence of an acid catalyst. The reaction is reversible, meaning that to drive it to completion, one must either remove the water produced or use an excess of one of the reactants. This method is commonly used in organic synthesis to create esters, which are important in various applications, including flavorings and fragrances.

Driving the Reaction to Completion

To drive the Fischer esterification reaction to completion, one effective method is to remove the water produced during the reaction. This can be achieved through techniques such as distillation or using a Dean-Stark apparatus. Alternatively, using an excess of either the carboxylic acid or the alcohol can shift the equilibrium towards the formation of the ester, thus increasing the yield of the desired product.

Structure of Ethyl Phenylacetate

Ethyl phenylacetate is an ester formed from phenylacetic acid and ethanol. Its structure consists of a phenyl group attached to a carbon chain that includes a carboxylate functional group, which is then esterified with an ethyl group. Understanding the molecular structure is crucial for predicting the reactivity and properties of the ester, as well as for designing the appropriate reaction conditions for its synthesis.

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Textbook Question

a. A student did not obtain any ester when he added 2,4,6-trimethylbenzoic acid to an acidic solution of ethanol. Why? (HINT: Build models.)

b. Would he have encountered the same problem if he had tried to synthesize the methyl ester of 4-methylbenzoic acid in the same way?

Textbook Question

Propose a mechanism for the following reaction. (Hint: Number the carbons to help you see where they end up in the product.)

Textbook Question

Show how each of the following esters could be prepared using a carboxylic acid as one of the starting materials:

a. methyl butyrate (odor of apples)

Textbook Question

Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(c)

(d)

Textbook Question

Predict the esterification products of the following acid/alcohol pairs.

(d)

(e)

Textbook Question

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

Textbook Question

Suggest the most appropriate reagent for each synthesis, and explain your choice.

(b)

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Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion. (c) ethyl phenylacetate

Key Concepts

Fischer Esterification

Driving the Reaction to Completion

Structure of Ethyl Phenylacetate

Watch next

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.
(c) ethyl phenylacetate