Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

16. Carboxylic Acids and Their Derivatives

Ester Reactions: Saponification

GOB Chemistry

16. Carboxylic Acids and Their Derivatives

Ester Reactions: Saponification

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2:36 minutes

Problem 26

Textbook Question

What are the products of the base hydrolysis of an ester?

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Understand the concept of base hydrolysis of an ester: Base hydrolysis, also known as saponification, involves the reaction of an ester with a strong base (e.g., NaOH or KOH) to produce a carboxylate salt and an alcohol.

Write the general chemical equation for the reaction: An ester (RCOOR') reacts with a strong base (e.g., NaOH) to form a carboxylate salt (RCOO⁻Na⁺) and an alcohol (R'OH).

Identify the functional groups involved: The ester group (-COOR') is cleaved during the reaction. The carbonyl carbon (C=O) becomes part of the carboxylate salt, while the alkoxy group (-OR') becomes the alcohol.

Explain the mechanism briefly: The hydroxide ion (OH⁻) attacks the carbonyl carbon of the ester, leading to the formation of a tetrahedral intermediate. This intermediate then breaks down, releasing the alcohol and forming the carboxylate salt.

Summarize the products: The products of base hydrolysis of an ester are a carboxylate salt (e.g., RCOO⁻Na⁺) and an alcohol (e.g., R'OH). These products depend on the specific ester and base used in the reaction.

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Key Concepts

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

Ester

An ester is a type of organic compound formed from the reaction between an alcohol and a carboxylic acid, characterized by the functional group -COO-. Esters are commonly used in the production of fragrances, flavorings, and as solvents. Understanding the structure and properties of esters is essential for predicting their behavior in chemical reactions, including hydrolysis.

Base Hydrolysis

Base hydrolysis, also known as saponification, is a chemical reaction where an ester reacts with a strong base, typically sodium hydroxide (NaOH), in the presence of water. This process breaks the ester bond, resulting in the formation of an alcohol and a carboxylate salt. Recognizing the conditions and products of base hydrolysis is crucial for understanding how esters can be transformed in chemical processes.

Products of Hydrolysis

The products of the base hydrolysis of an ester are an alcohol and a carboxylate salt. For example, when ethyl acetate undergoes hydrolysis with sodium hydroxide, it produces ethanol and sodium acetate. Identifying these products is important for applications in organic chemistry, particularly in the synthesis and analysis of various compounds.

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Related Practice

Textbook Question

Ethyl octanoate is a flavor component of mangoes.

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e. How many milliliters of a 0.315 M NaOH solution is needed to completely hydrolyze (saponify) 2.84 g of ethyl octanoate?

420

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Textbook Question

Propyl acetate is the ester that gives the odor and smell of pears.

d. Use condensed structural formulas to write the balanced chemical equation for the base hydrolysis of propyl acetate with NaOH.

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Multiple Choice

Name alcohol formed when the following ester undergoes a saponification reaction.

Household soap is a mixture of the sodium or potassium salts of long-chain carboxylic acids that arise from saponification of animal fat.

b. Draw the structures of the soap molecules produced in the following reaction:

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Textbook Question

Draw the condensed structural or line-angle formulas for the products from the acid- or base-catalyzed hydrolysis of each of the following:

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Textbook Question

Draw the condensed structural or line-angle formulas for the products of the following:

432

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Textbook Question

Draw the condensed structural or line-angle formulas for the products of the following:

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Textbook Question

Propyl acetate is the ester that gives the odor and smell of pears.

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d. Write the balanced chemical equation for the base hydrolysis of propyl acetate with NaOH.

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