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Ch.23 Lipids
McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Capitolo 23, Problema 38

Draw the structure of glyceryl trilaurate, which is made from glycerol and three lauric acid molecules.

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Understand the components: Glyceryl trilaurate is a triester formed from glycerol (a three-carbon molecule with three hydroxyl groups, \( \text{C}_3\text{H}_8\text{O}_3 \)) and three lauric acid molecules (a 12-carbon saturated fatty acid, \( \text{C}_{12}\text{H}_{24}\text{O}_2 \)).
Recognize the esterification process: Each hydroxyl group on glycerol reacts with the carboxylic acid group (\( \text{-COOH} \)) of lauric acid to form an ester bond (\( \text{-COO} \)) and release water (\( \text{H}_2\text{O} \)).
Draw the glycerol backbone: Start with a vertical chain of three carbon atoms, each bonded to a hydroxyl group (\( \text{-OH} \)) and sufficient hydrogens to satisfy the valency of carbon.
Attach the lauric acid chains: Replace each hydroxyl group on glycerol with an ester bond (\( \text{-COO} \)) connected to the 12-carbon chain of lauric acid. Ensure that each lauric acid chain is fully saturated (no double bonds) and ends with a methyl group (\( \text{-CH}_3 \)).
Verify the structure: Confirm that the final structure has three ester bonds, a glycerol backbone, and three lauric acid chains, each containing 12 carbons. The molecular formula of glyceryl trilaurate should be \( \text{C}_{39}\text{H}_{74}\text{O}_6 \).

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Glycerol Structure

Glycerol, also known as glycerin, is a simple polyol compound with three hydroxyl (–OH) groups. Its structure consists of a three-carbon chain, where each carbon is attached to a hydroxyl group. This unique structure allows glycerol to act as a backbone for triglycerides, forming the basis for lipid molecules like glyceryl trilaurate.
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Glycerol Metabolism Concept 2

Fatty Acids

Fatty acids are long hydrocarbon chains with a carboxylic acid group at one end. Lauric acid, specifically, is a saturated fatty acid with a 12-carbon chain. When fatty acids like lauric acid react with glycerol, they form esters, which are the building blocks of triglycerides, such as glyceryl trilaurate.
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Fatty Acids Concept 1

Esterification Reaction

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 glyceryl trilaurate, glycerol undergoes esterification with three lauric acid molecules, leading to the formation of a triglyceride. This reaction is crucial in the synthesis of fats and oils in biological systems.
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Ester Reactions: Esterification Example 1