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: Esterification

GOB Chemistry

16. Carboxylic Acids and Their Derivatives

Ester Reactions: Esterification

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Problem 80

Textbook Question

Write the formula of the triester formed from glycerol and stearic acid.

Verified step by step guidance

Identify the structure of glycerol: Glycerol is a triol, meaning it has three hydroxyl (-OH) groups attached to a three-carbon backbone. Its chemical formula is C₃H₈O₃.

Identify the structure of stearic acid: Stearic acid is a saturated fatty acid with the chemical formula C₁₇H₃₅COOH. It contains a carboxylic acid (-COOH) group and a long hydrocarbon chain.

Understand the reaction: A triester is formed when glycerol reacts with three molecules of a fatty acid (in this case, stearic acid) through an esterification reaction. Each hydroxyl group of glycerol reacts with the carboxylic acid group of stearic acid, releasing water (H₂O) and forming an ester bond.

Write the general formula for the triester: The resulting triester will have the glycerol backbone with three stearic acid chains attached via ester bonds. The formula can be written as C₃H₅(OCOC₁₇H₃₅)₃, where each hydroxyl group of glycerol is replaced by an ester group (-OCOC₁₇H₃₅).

Verify the structure: Ensure that the triester has three ester linkages, one for each hydroxyl group of glycerol, and that the stearic acid chains are correctly attached. This confirms the formation of the triester from glycerol and stearic acid.

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Key Concepts

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

Glycerol

Glycerol, also known as glycerin, is a simple polyol compound that serves as a backbone for triglycerides and phospholipids. It consists of three carbon atoms, each bonded to a hydroxyl group (-OH). In the context of esterification, glycerol reacts with fatty acids to form esters, specifically triglycerides, which are important in biological systems as energy storage molecules.

Stearic Acid

Stearic acid is a saturated fatty acid with an 18-carbon chain, commonly found in animal and plant fats. Its chemical formula is C18H36O2, and it plays a crucial role in the formation of triglycerides. When stearic acid reacts with glycerol, it forms a triester, which is a type of lipid that is a major component of dietary fats and oils.

Esterification

Esterification is a chemical reaction between an alcohol and a carboxylic acid, resulting in the formation of an ester and water. In the case of glycerol and stearic acid, the reaction involves the hydroxyl groups of glycerol and the carboxyl group of stearic acid, leading to the formation of a triester known as a triglyceride. This process is fundamental in biochemistry, particularly in the synthesis of fats.

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Consider the following unnatural amino acid:

a. If two molecules react to form an ester, what is the structure of the ester product?

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Textbook Question

Consider the following unnatural amino acid:

c. Draw the cyclic ester resulting from the intramolecular reaction of the hydroxyl group of this amino acid with its carboxyl group (cyclic esters are called lactones).

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Draw structures of the carboxylic acids and alcohols you would use to prepare each ester in Problem 17.54.

c. Cyclohexyl acetate

d. Phenyl-o-hydroxybenzoate

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Each of the following materials has an ester that is responsible for its smell and/or flavor. Search the internet and determine what that ester is, draw its structure, and what carboxylic acid and alcohol are used to form it.

a. Juicy Fruit gum flavoring

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Give the structure of the repeating units in the polymers that are formed in the reactions of the following compounds.

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Write both condensed and line structures for (a) the ester formed when butyric acid reacts with cyclopentanol.

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