1. Chapter Sixteen Carboxylic Acids, Esters, and Other Acid Derivatives

2. Copyright © Houghton Mifflin Company. All rights reserved.16 | 2 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d © Bilderberg / Peter Arnold, Inc. →CO 16.1

3. Copyright © Houghton Mifflin Company. All rights reserved.16 | 3 Fig. 16.1 The three simplest carboxylic acids: methanoic acid, ethanoic acid, and propanoic acid. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

4. Copyright © Houghton Mifflin Company. All rights reserved.16 | 4 →Fig. 16.2 Benzoic acid molecule Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

5. Copyright © Houghton Mifflin Company. All rights reserved.16 | 5 →Table 16.1 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

6. Copyright © Houghton Mifflin Company. All rights reserved.16 | 6 →Fig. 16.3 “Drug-sniffing” dogs used by narcotics agents can find hidden heroin by detecting the odor of acetic acid. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

7. Copyright © Houghton Mifflin Company. All rights reserved.16 | 7 →Table 16.2 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

8. Copyright © Houghton Mifflin Company. All rights reserved.16 | 8 ←CC 16.2 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

9. Copyright © Houghton Mifflin Company. All rights reserved.16 | 9 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d ←CC 16.1

10. Copyright © Houghton Mifflin Company. All rights reserved.16 | 10 →Fig. 16.5 Tartaric acid is particularly abundant in ripe grapes. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d F. Stewart Westomreland / Photo Researchers

11. Copyright © Houghton Mifflin Company. All rights reserved.16 | 11 ←Fig. 16.6 Structural characteristics and functions of several polyfunctional carboxylic acids that are important in metabolic reactions in the human body. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

12. Copyright © Houghton Mifflin Company. All rights reserved.16 | 12 →Fig. 16.7 The boiling points of mono-carboxylic acids are compared to those of other types of compounds. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

13. Copyright © Houghton Mifflin Company. All rights reserved.16 | 13 ←Fig. 16.8 Unbranched mono and dicarboxylic acids at room temperature and pressure. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

14. Copyright © Houghton Mifflin Company. All rights reserved.16 | 14 →Fig. 16.9 A given carboxylic acid molecule can form two hydrogen bonds to another carboxylic acid molecule, producing a “dimer.” Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

15. Copyright © Houghton Mifflin Company. All rights reserved.16 | 15 ←Fig. 16.10 The solubility in water of saturated unbranched-chain carboxylic acids. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

16. Copyright © Houghton Mifflin Company. All rights reserved.16 | 16 Table 16.3 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

17. Copyright © Houghton Mifflin Company. All rights reserved.16 | 17 →Fig. 16.11 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

18. Copyright © Houghton Mifflin Company. All rights reserved.16 | 18 ←Fig. 16.12 Methyl and ethyl esters of acetic acid. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

19. Copyright © Houghton Mifflin Company. All rights reserved.16 | 19 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d ←CAG 16.1.

20. Copyright © Houghton Mifflin Company. All rights reserved.16 | 20 →Table 16.4 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

21. Copyright © Houghton Mifflin Company. All rights reserved.16 | 21 →Fig. 16.13 Cats of all types are strongly attracted to the catnip plant, which has cyclic ester. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d Fred Whitehead / Animals Animals

22. Copyright © Houghton Mifflin Company. All rights reserved.16 | 22 CC 16.3 Aspirin Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

23. Copyright © Houghton Mifflin Company. All rights reserved.16 | 23 Table 16.5 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

24. Copyright © Houghton Mifflin Company. All rights reserved.16 | 24 ←Fig. 16.14 Ester-water hydrogen bonding Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

25. Copyright © Houghton Mifflin Company. All rights reserved.16 | 25 →Fig. 16.15 Methyl and ethyl esters of unbranched-chain carboxylic acids at room temperature and pressure. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

26. Copyright © Houghton Mifflin Company. All rights reserved.16 | 26 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d →CAG 16.2

27. Copyright © Houghton Mifflin Company. All rights reserved.16 | 27 ←Fig. 16.16 A segment of the polyester condensation polymer known as poly(ethylene terephthalate), or PET. Carboxylic Acids, Esters, and Other Acid Derivatives cont’d

28. Copyright © Houghton Mifflin Company. All rights reserved.16 | 28 Carboxylic Acids, Esters, and Other Acid Derivatives cont’d Custom Medical Stock Photo →CAG 16.4