Textbook Question
Can there be any chiral carbon atoms in triacylglycerols? If so, which ones can be chiral and what determines their chirality?
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Ch.23 Lipids
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 23, Problem 13a
Identify the products formed by complete hydrolysis of all ester bonds in (a) the phosphatidylcholine on page 726.
Verified step by step guidance1
Understand the structure of phosphatidylcholine: It is a type of phospholipid composed of a glycerol backbone, two fatty acid chains attached via ester bonds, a phosphate group, and a choline group attached to the phosphate.
Recognize that hydrolysis of ester bonds involves breaking the bond between the oxygen atom of the ester group and the carbon atom of the carbonyl group, using water as a reactant.
Identify the ester bonds in phosphatidylcholine: (1) Two ester bonds between the glycerol backbone and the fatty acid chains, and (2) one ester bond between the glycerol backbone and the phosphate group.
Determine the products of hydrolysis: (1) The two fatty acid chains will be released as free fatty acids, (2) the glycerol backbone will be released as glycerol, and (3) the phosphate group will be released as a phosphate ion, which remains attached to the choline group as phosphocholine.
Summarize the products: The complete hydrolysis of phosphatidylcholine will yield two free fatty acids, glycerol, and phosphocholine (a combination of phosphate and choline).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ester Bonds
Ester bonds are chemical linkages formed between an alcohol and a carboxylic acid, resulting in the release of water. In the context of phospholipids like phosphatidylcholine, these bonds connect fatty acid chains to a glycerol backbone. Complete hydrolysis of ester bonds involves breaking these linkages, which is essential for understanding the products formed during the reaction.
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Phosphatidylcholine Structure
Phosphatidylcholine is a type of phospholipid that consists of a glycerol backbone, two fatty acid chains, and a phosphate group attached to a choline molecule. This structure is crucial for cell membrane integrity and function. Understanding its composition helps in predicting the products of hydrolysis, which will include glycerol, fatty acids, and choline.
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Complete Hydrolysis
Complete hydrolysis refers to the process of breaking down a compound into its constituent parts by the addition of water. In the case of phosphatidylcholine, this means fully breaking down all ester bonds to yield free fatty acids, glycerol, and choline. This concept is vital for determining the end products of the hydrolysis reaction.
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Related Practice
Textbook Question
Write an equation for the complete hydrogenation of triolein, the triacylglycerol with three oleic acid acyl groups for which you drew the structure in Problem 23.3. Name the fatty acid from which the resulting acyl groups are derived.
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Textbook Question
Write the complete equation for the hydrolysis of a triacylglycerol in which the fatty acids are two molecules of stearic acid and one of oleic acid.
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Textbook Question
Identify the products formed by complete hydrolysis of all ester bonds in (b) the sphingomyelin in Figure 23.5.
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Textbook Question
Draw the structure of the sphingomyelin that contains a myristic acid acyl group. Identify the hydrophilic head group and the hydrophobic tails in this molecule.
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Textbook Question
Draw the structure of the glycerophospholipid that contains a stearic acid acyl group, an oleic acid acyl group, and a phosphate bonded to ethanolamine.
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