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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3:36 minutes

Problem 34b

Textbook Question

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

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Step 1: Analyze the transformation. The starting material is salicylic acid (a benzene ring with an -OH group and a -COOH group in ortho positions). The product is methyl salicylate, where the -COOH group has been converted into a methyl ester (-COOCH3). This indicates an esterification reaction.

Step 2: Identify the reagent required for esterification. Esterification typically involves reacting a carboxylic acid (-COOH) with an alcohol (e.g., methanol, CH3OH) in the presence of an acid catalyst, such as concentrated sulfuric acid (H2SO4). The acid catalyst helps protonate the carboxylic acid, making it more reactive.

Step 3: Write the general reaction mechanism. The carboxylic acid (-COOH) reacts with methanol (CH3OH) under acidic conditions. The hydroxyl group (-OH) of the carboxylic acid is replaced by the methoxy group (-OCH3) from methanol, forming the ester (-COOCH3). Water (H2O) is produced as a byproduct.

Step 4: Explain why methanol and sulfuric acid are appropriate choices. Methanol provides the methyl group (-CH3) needed for the ester, while sulfuric acid acts as a catalyst to speed up the reaction and ensure the formation of the ester. This combination is commonly used for esterification reactions.

Step 5: Summarize the synthesis. To convert salicylic acid into methyl salicylate, react salicylic acid with methanol in the presence of concentrated sulfuric acid. Heat the reaction mixture to facilitate the esterification process, and isolate the product after completion.

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Key Concepts

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

Reagent Selection

Choosing the right reagent is crucial in organic synthesis as it determines the efficiency and outcome of the reaction. The selected reagent must be compatible with the starting materials and the desired product, taking into account factors such as reactivity, selectivity, and functional group compatibility.

Reaction Mechanisms

Understanding the underlying reaction mechanisms is essential for predicting how reagents will interact with substrates. This includes knowledge of nucleophiles, electrophiles, and the types of reactions (e.g., substitution, addition, elimination) that can occur, which helps in rationalizing the choice of reagents.

Functional Group Transformations

Functional groups dictate the chemical behavior of organic molecules. Recognizing the functional groups present in the reactants and the desired product allows chemists to select reagents that can effectively transform one functional group into another, facilitating the synthesis of complex molecules.

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Related Practice

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.

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

Show how you would convert alanine to the following derivatives. Show the structure of the product in each case.

(a) alanine isopropyl ester

(b) N-benzoylalanine

Textbook Question

Show how each of the following compounds can be prepared, using the given starting material:

Textbook Question

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.

(f)

Textbook Question

Show the alcohol and the acid chloride that combine to make the following esters.

(c)

(d)

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

Key Concepts

Reagent Selection

Reaction Mechanisms

Functional Group Transformations

Watch next

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