Textbook Question
Which of the following are saponifiable lipids? (Recall that ester bonds are broken by base hydrolysis.)
a. Progesterone
b. Glyceryl trioleate
c. A sphingomyelin
d. Prostaglandin E1
e. A cerebroside
f. A lecithin
Ch.23 Lipids
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 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
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 23, Problem 77
Identify the component parts of each saponifiable lipid listed in Problem 23.76.
a. Progesterone
b. Glyceryl trioleate
c. A sphingomyelin
d. Prostaglandin
e. A cerebroside
f. A lecithin
Verified step by step guidance1
Understand the term 'saponifiable lipid': Saponifiable lipids are lipids that can be hydrolyzed in the presence of a strong base (like NaOH or KOH) to produce glycerol and fatty acid salts (soaps). Examples include triglycerides, phospholipids, and waxes.
Review the structure of the lipid in question: For each lipid listed in Problem 23.76, identify whether it is a triglyceride, phospholipid, or wax. This will help determine its component parts.
Break down the structure of the lipid: For triglycerides, identify the glycerol backbone and the three fatty acid chains. For phospholipids, identify the glycerol backbone, two fatty acid chains, and the phosphate group with its attached molecule. For waxes, identify the long-chain alcohol and the fatty acid.
Write the hydrolysis reaction: Represent the saponification reaction for each lipid. For example, for a triglyceride, the reaction would involve the lipid reacting with NaOH to produce glycerol and three fatty acid salts.
Summarize the component parts: After hydrolysis, list the products for each lipid. For triglycerides, the products are glycerol and fatty acid salts. For phospholipids, the products are glycerol, fatty acid salts, and a phosphate-containing group. For waxes, the products are a long-chain alcohol and a fatty acid salt.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Saponifiable Lipids
Saponifiable lipids are a category of lipids that can be hydrolyzed into their constituent fatty acids and glycerol through a process called saponification. This process typically involves the reaction of lipids with an alkali, resulting in the formation of soap and glycerin. Common examples include triglycerides and phospholipids, which are essential for various biological functions.
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Fatty Acids
Fatty acids are carboxylic acids with long hydrocarbon chains, which can be saturated (no double bonds) or unsaturated (one or more double bonds). They are the building blocks of saponifiable lipids and play a crucial role in energy storage, cellular structure, and signaling. Understanding the types and structures of fatty acids is essential for analyzing the properties of lipids.
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Glycerol
Glycerol is a three-carbon alcohol that serves as the backbone for triglycerides and phospholipids. Each of the three hydroxyl (-OH) groups in glycerol can form an ester bond with fatty acids, resulting in the formation of saponifiable lipids. Glycerol is also important in metabolism and can be converted into glucose or used in the synthesis of other biomolecules.
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Related Practice
Textbook Question
Draw cholesterol acetate. Is this molecule saponifiable? Explain.
Textbook Question
Draw the structure of a triacylglycerol made from two molecules of myristic acid and one molecule of linolenic acid.
Textbook Question
Based on the information in Section 23.7, how would you expect each of these common metabolites to cross the cell membrane?
a. CO
Textbook Question
Based on the information in Section 23.7, how would you expect each of these common metabolites to cross the cell membrane?
c. Ca2+
Textbook Question
If the average molar mass of a sample of soybean oil is 1500 g/mol, how many grams of NaOH are needed to saponify 5.0 g of the oil?