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

Previous problemNext problem

3:49 minutes

Problem 31a

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)

Verified step by step guidance

Identify the structure of methyl butyrate. Methyl butyrate is an ester with the formula CH₃CH₂CH₂COOCH₃. It consists of a butanoic acid-derived portion (CH₃CH₂CH₂CO-) and a methyl group (-OCH₃).

Recall the general method for ester synthesis: Esters are typically prepared via Fischer esterification, which involves reacting a carboxylic acid with an alcohol in the presence of an acid catalyst (e.g., H₂SO₄).

Determine the carboxylic acid and alcohol needed to form methyl butyrate. The carboxylic acid must be butanoic acid (CH₃CH₂CH₂COOH), and the alcohol must be methanol (CH₃OH).

Write the reaction equation for the synthesis: CH₃CH₂CH₂COOH + CH₃OH → CH₃CH₂CH₂COOCH₃ + H₂O. This reaction is catalyzed by an acid, such as H₂SO₄, to promote the formation of the ester bond.

Describe the reaction conditions: Combine butanoic acid and methanol in a reaction flask, add a few drops of concentrated sulfuric acid as the catalyst, and heat the mixture under reflux. After the reaction is complete, the ester can be purified by distillation or extraction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Esterification

Esterification is a chemical reaction that forms an ester from a carboxylic acid and an alcohol. This process typically involves the condensation of the two reactants, resulting in the elimination of water. The reaction can be catalyzed by an acid, which helps to increase the reaction rate. Understanding this process is crucial for synthesizing esters like methyl butyrate.

Carboxylic Acids

Carboxylic acids are organic compounds characterized by the presence of a carboxyl group (-COOH). They are key starting materials in ester synthesis, as they provide the acid component needed for esterification. The specific carboxylic acid used will influence the structure and properties of the resulting ester, making it essential to select the appropriate acid for the desired ester.

Alcohols

Alcohols are organic compounds containing one or more hydroxyl groups (-OH) attached to a carbon atom. In the context of ester synthesis, the choice of alcohol is critical, as it determines the alkyl portion of the ester. For methyl butyrate, methanol is the alcohol used, and understanding its role in the esterification process is vital for successful synthesis.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

(a) CH₃CH₂CH₂COOH + CH₃OH

(b) CH₃OH + HNO₃

Textbook Question

When butanoic acid and ¹⁸O-labeled methanol react under acidic conditions, what compounds are labeled when the reaction has reached equilibrium?

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

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

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)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

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)

Key Concepts

Esterification

Carboxylic Acids

Alcohols

Watch next

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)