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Understanding Carboxylic Acids, Fatty Acids, and Lipids: Structure and Function

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This chapter explores the structure, properties, and reactions of carboxylic acids and their derivatives, particularly focusing on lipids, including waxes, triglycerides, and fatty acids. It examines the significance of saturated and unsaturated fatty acids, their melting points, and the soap-making process through saponification. Additionally, the role of steroids, including cholesterol and sex hormones, is discussed. The content is part of a comprehensive presentation suited for organic chemistry learners at Burlington County College.

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Understanding Carboxylic Acids, Fatty Acids, and Lipids: Structure and Function

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  1. CHE 242Unit VIIIThe Structure, Properties, Reactions and Mechanisms of Carboxylic Acids and Their DerivativesCHAPTER TWENTY-FIVE Terrence P. Sherlock Burlington County College 2004

  2. Examples of Lipids => Chapter 25

  3. Waxes • Esters of long-chain fatty acids with long-chain alcohols. • Spermaceti is found in the head of the sperm whale and is probably used to control buoyancy. • Most natural waxes are protective coats for plants’ leaves, insects’ exoskeleton, mammals’ fur, and birds’ feathers. => Chapter 25

  4. Triglycerides • Fatty acid esters of glycerol. • Fats • Solid at room temperature • Most are derived from mammals • Oils • Liquid at room temperature • Most are derived from plants or cold-blooded animals. => Chapter 25

  5. Fatty Acids • Unbranched carboxylic acids with 12-20 carbons. • Most contain an even number of carbons because they are built from acetic acid units. • Melting points increase with increasing molecular weights. • Unsaturation greatly lowers the melting point. => Chapter 25

  6. => Melting Points • A cis double bond bends the molecule so it cannot pack efficiently. • A trans double bond has less effect. Chapter 25

  7. => Fats and Oils • Most fats have saturated fatty acids. • Most oils have unsaturated fatty acids. Chapter 25

  8. => A soap Saponification • “Soap-making” • Base-catalyzed hydrolysis of ester linkages in fats and oils. Chapter 25

  9. Soap Structure => Chapter 25

  10. Grease in Soap Solution => Chapter 25

  11. Detergents => Chapter 25

  12. Steroids • Polycyclic, usually all trans. • Common structural features: • =O or -OH at C3 • Side chain at C17 • Double bond from C5 to either C4 or C6. => Chapter 25

  13. => A-B Ring Junction May be cis, but usually is trans. Chapter 25

  14. Cholesterol • Common biological intermediate. • Probably a precursor to other steroids. • Side chain at C17 and double bond C5-C6. => Chapter 25

  15. Sex Hormones • Female hormone has an aromatic ring and one less methyl group than the male hormone. • Testosterone is converted to estradiol in the ovaries. => Chapter 25

  16. POWER POINT IMAGES FROM “ORGANIC CHEMISTRY, 5TH EDITION”L.G. WADEALL MATERIALS USED WITH PERMISSION OF AUTHORPRESENTATION ADAPTED FOR BURLINGTON COUNTY COLLEGEORGANIC CHEMISTRY COURSEBY:ANNALICIA POEHLER STEFANIE LAYMAN CALY MARTIN Chapter 25

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