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Chapter 17 Carboxylic Acids And Esters

Chapter 17 Carboxylic Acids And Esters. 17.1 Carboxylic Acids 17.2 Physical Properties of Carboxylic Acids 17.3 Acidity of Carboxylic Acids. Carboxyl Group. The carboxyl group: Is a carbonyl group (C=O) attached to a hydroxyl group (OH).

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Chapter 17 Carboxylic Acids And Esters

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  1. Chapter 17 Carboxylic Acids And Esters 17.1 Carboxylic Acids 17.2 Physical Properties of Carboxylic Acids 17.3 Acidity of Carboxylic Acids

  2. Carboxyl Group The carboxyl group: • Is a carbonyl group (C=O) attached to a hydroxyl group (OH). • Is found on carbon 1 in carboxylic acids. • Is written in different ways. O  CH3—C—OH CH3—COOH CH3—CO2H

  3. Models of Carboxylic Acids • The three-dimensional models show the geometry of atoms in carboxylic acid molecules.

  4. IUPAC Names The IUPAC names of carboxylic acids: • Replace the -e in the alkane name with -oic acid. CH4 methane HCOOH methanoic acid CH3—CH3 ethane CH3—COOH ethanoic acid • Number substituents from the carboxyl carbon 1. CH3 | CH3—CH—CH2—COOH 4 3 2 1 3-methylbutanoic acid

  5. Common Names The common names of simple carboxylic acids: • Use formic acid (1C), acetic acid (2C), propionic acid (3C), and butyric acid (4C). HCOOH formic acid CH3—COOH acetic acid • Locate substituents by assigning , , γ to the carbon atoms adjacent to the carboxyl carbon. CH3 γ| CH3—CH—CH2—COOH -methylbutryic acid

  6. Names and Sources of Some Carboxylic Acids

  7. Aromatic Carboxylic Acids Benzoic acid: • Is the aromatic carboxylic acid. • Locates substituents by assigning 1 to the carbon attached to the carboxyl group. • Has common names that assign prefixes ortho, meta, and para for 2 substituents. ortho 1, 2 location meta 1, 3 location para 1, 4 location

  8. Aromatic Carboxylic Acids

  9. Alpha Hydroxy Acids Alpha hydroxy acids (AHAs): • Occur naturally in fruit, milk, and sugarcane. • Are used in skin care products.

  10. Preparation of Carboxylic Acids • Carboxylic acid can be prepared by oxidizing primary alcohols or aldehydes. • The oxidation of ethanol produces ethanoic acid (acetic acid). OH O O | [O] || [O] || CH3—CH2 CH3—C—HCH3—C—OH Ethanol ethanal ethanoic acid Ethyl alcohol acetaldehyde acetic acid

  11. Boiling Points Carboxylic acids: • Have higher boiling points than alcohols, ketones, and aldehydes of similar mass. • Form dimers in which hydrogen bonds form between two carboxyl groups. O H—O || | CH3cC C—CH3 | || O—H O A dimer of acetic acid

  12. Solubility in Water Carboxylic acids: • With 1-4 carbon atoms are very soluble in water. • Form hydrogen bonds with many water molecules.

  13. Boiling Points and Solubility

  14. Acid Dissociation Constants Carboxylic acids: • Are weak acids. CH3—COOH + H2O CH3—COO– + H3O+ • Exist mostly as molecules and a few ions in aqueous solutions. • Have small Ka values.

  15. Salts of Carboxylic Acids Carboxylic acid salts are: • Formed when a carboxylic acid is neutralized by a strong base. CH3—COOH + NaOH CH3—COO– Na+ + H2O acetic acid sodium acetate (carboxylic acid salt) • Used as preservatives and flavor enhancers.

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