Ch.23 Lipids

McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition

McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook

McMurry 8th Edition

Ch.23 Lipids

Problem 13b

Chapter 23, Problem 13b

Identify the products formed by complete hydrolysis of all ester bonds in (b) the sphingomyelin in Figure 23.5.

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Identify the structure of sphingomyelin from Figure 23.5. Sphingomyelin is a type of sphingolipid that contains a sphingosine backbone, a fatty acid attached via an amide bond, and a phosphate group attached to a choline group.

Understand the concept of hydrolysis. Hydrolysis is a chemical reaction where water is used to break bonds. In the case of sphingomyelin, hydrolysis will break the ester bonds and the amide bond.

Focus on the ester bonds in sphingomyelin. These are found between the phosphate group and the choline group, as well as between the phosphate group and the sphingosine backbone. Hydrolysis of these bonds will yield choline, phosphate, and the sphingosine backbone.

Consider the amide bond between the sphingosine backbone and the fatty acid. Hydrolysis of this bond will release the fatty acid and the sphingosine backbone as separate products.

Combine the products from the hydrolysis reactions. The complete hydrolysis of sphingomyelin will yield choline, phosphate, a fatty acid, and sphingosine as the final products.

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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 biological molecules, such as lipids, these bonds are crucial for the structure and function of compounds like sphingomyelin. Complete hydrolysis of ester bonds involves breaking these linkages, leading to the release of the constituent fatty acids and alcohols.

Sphingomyelin

Sphingomyelin is a type of sphingolipid that is a major component of cell membranes, particularly in the myelin sheath of nerve cells. It consists of a sphingosine backbone, a fatty acid, and a phosphocholine group. Understanding its structure is essential for predicting the products of hydrolysis, as the breakdown will yield sphingosine, fatty acids, and phosphoric acid.

Complete Hydrolysis

Complete hydrolysis refers to the process of breaking down a compound into its constituent parts by the addition of water. In the context of sphingomyelin, this means fully cleaving all ester bonds to release all fatty acids and other components. This process is significant in biochemistry for understanding how lipids are metabolized and utilized in biological systems.

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Related Practice

Textbook Question

Which of the following terms apply to the compound shown below? (Hint: Look at the functional groups and the bonds involved to begin analyzing the compound part by part in comparison to the lipids discussed in this chapter.)

a. A phospholipid

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.

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.

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.

Textbook Question

Identify the products formed by complete hydrolysis of all ester bonds in (a) the phosphatidylcholine on page 726.

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.