Textbook Question
Propanamide and methyl acetate have about the same molar mass, both are quite soluble in water, and yet the boiling point of propanamide is 213 °C, whereas that of methyl acetate is 57 °C. Explain.
Ch.17 Carboxylic Acids and Their Derivatives
McMurry8th EditionFundamentals of GOBISBN: 9780134015187
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Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
Chapter 17, Problem 80
Write the formula of the triester formed from glycerol and stearic acid.
Verified step by step guidance1
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.
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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.
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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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Related Practice
Textbook Question
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
Textbook Question
What is the difference between a phosphate diester and an ester of a diphosphate? Give an example of each.
Textbook Question
Mention at least two simple chemical tests by which you can distinguish between benzaldehyde and benzoic acid.
Textbook Question
Draw all possible carboxylic acids with the formula C5H10O2.