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Chapter 15

Chapter 15. Carboxylic Acids, Esters, and derivatives. Where found. Tartness in fruits Rancid butter Animal fats and plant oil Clothing. Structure of Carboxylic Acids. Presence of the carbonyl group: C=O Additional presence of Formic acid Acetic acid. Structure of Esters.

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Chapter 15

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  1. Chapter 15 Carboxylic Acids, Esters, and derivatives

  2. Where found • Tartness in fruits • Rancid butter • Animal fats and plant oil • Clothing

  3. Structure of Carboxylic Acids • Presence of the carbonyl group: C=O • Additional presence of • Formic acid • Acetic acid

  4. Structure of Esters • A carboxylic acid derivative • Presence • Methyl propionate

  5. Structure of Acid Anhydrides • Presence of two carbonyl carbons connected by an oxygen

  6. Structure of Amides • Presence of • More in chapter 16

  7. Structure of Acid Halide • Presence of

  8. Synthesis of Carboxylic Acids • Selective oxidation • Benzoic acid • From

  9. Naming Carboxylic Acids • Longest chain with carboxyl group. The carboxyl carbon is C1 • Ending of –e is changed to –oic acid • Substituents are used as prefixes with numbers to show location • Two carboxyl groups are an alkanedioic acid with separate numbers to show location

  10. Items of Interest • Table 15.2 page 437 • Box 15.1 page 441

  11. Properties of Carboxylic Acids • How do the m.p. and b.p. compare to: • Alkanes? • Alcohols? • How does solubility compare to: • Alkanes? • Alcohols

  12. Acidity of Carboxylic Acids • Weak acids • Only about 1 to 2% ionization to H+ • HCl is 100% ionized • Acidic enough to turn blue litmus red

  13. Carboxylate Salts • More soluble in higher pH environment (i.e. blood) • Important in biological functions

  14. Properties of Carboxylate Salts • Ionic molecules • Injections of medicine with a carboxyl groups are given with the salt • The salts are basic – red to blue litmus

  15. Naming Carboxylate Salts • Positive ion named first • Change the acid from –ic acid to –ate • Name: • CH3COO-Na+ • CH3CH2CH2CH2COO-K+

  16. Soaps • Salts of long chain carboxylic acids (fatty acids – derived from animals and plants) • Conversion process is called • Sodium stearate CH3(CH2)16COO-Na+ • Need a long chain and ionic head (Fig 15.1)

  17. Esters • An ester, RCOOR’ is formed • Process is called esterification • Thioesters – involve Sulfur (Thiol) p. 446

  18. Naming Esters • Two parts • Alkoxy – alcohol (aryloxy for phenol) • Acyl – acid • The group is named first • The part is named second and change from –ic acid to –ate • Name: CH3OOC(CH2)3CH3

  19. Polyesters • Esterification becomes polymerization if there are two functional groups per molecule • Dicarboxylic acids • Diols • See page 449 • Condensation reaction if water is a by-product • Addition polymerization if no by-products (alkenes)

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