1. Chapter Fourteen Alcohols, Phenols, And Ethers

2. Copyright © Houghton Mifflin Company. All rights reserved.14 | 2 Alcohols, Phenols, and Ethers cont’d © Ed Reschke/Peter Arnold, Inc.  CO 14.1

3. Copyright © Houghton Mifflin Company. All rights reserved.14 | 3 Fig. 14.1 Space-filling models for the three simplest unbranched chain alcohols: methyl alcohol, ethyl alcohol, and propyl alcohol. Alcohols, Phenols, and Ethers cont’d

4. Copyright © Houghton Mifflin Company. All rights reserved.14 | 4 →Fig. 14.2 The similar shapes of water and methanol. Methyl alcohol may be viewed structurally as an alkyl derivative of water. Alcohols, Phenols, and Ethers cont’d

5. Copyright © Houghton Mifflin Company. All rights reserved.14 | 5 →Table 14.1 Alcohols, Phenols, and Ethers cont’d

6. Copyright © Houghton Mifflin Company. All rights reserved.14 | 6 ←Fig. 14.3 Racing cars are fueled with methyl alcohol. Alcohols, Phenols, and Ethers cont’d Jonathan Ferrey/Getty Images

7. Copyright © Houghton Mifflin Company. All rights reserved.14 | 7  Table 14.2 Alcohols, Phenols, and Ethers cont’d

8. Copyright © Houghton Mifflin Company. All rights reserved.14 | 8 ←Fig. 14.5 Ethylene glycol is the major ingredient in de- icers for planes. Alcohols, Phenols, and Ethers cont’d © Hank Morgan/Rainbow

9. Copyright © Houghton Mifflin Company. All rights reserved.14 | 9 →Fig. 14.6 For survival in northern winters, many fish and insects produce large amount of glycerol that dissolve in their blood, thereby lowering the freezing point. Alcohols, Phenols, and Ethers cont’d James Cotier/Getty Images

10. Copyright © Houghton Mifflin Company. All rights reserved.14 | 10 ←CC 14.1 Cough drops Alcohols, Phenols, and Ethers cont’d

11. Copyright © Houghton Mifflin Company. All rights reserved.14 | 11 Fig. 14.7 (a) The polar hydroxyl functional group dominates the physical properties of methanol. (b) Conversely, the nonpolar portion of 1- octanol dominates its physical properties. Alcohols, Phenols, and Ethers cont’d

12. Copyright © Houghton Mifflin Company. All rights reserved.14 | 12 ←Fig. 14.8 (a) Boiling points and (b) solubilities in water of selected 1- alcohols. Alcohols, Phenols, and Ethers cont’d

13. Copyright © Houghton Mifflin Company. All rights reserved.14 | 13 →Fig. 14.9 Physical state summary for unbranched 1- alcohols and unsubstituted cycloalcohols at room temperature and pressure. Alcohols, Phenols, and Ethers cont’d

14. Copyright © Houghton Mifflin Company. All rights reserved.14 | 14 Table 14.3 Alcohols, Phenols, and Ethers cont’d

15. Copyright © Houghton Mifflin Company. All rights reserved.14 | 15 ←Fig. 14.10 Alcohol boiling points are higher than those of the corresponding alkanes because of the alcohol-alcohol hydrogen bonding. Alcohols, Phenols, and Ethers cont’d

16. Copyright © Houghton Mifflin Company. All rights reserved.14 | 16 →Fig. 14.11 Because of hydrogen bonding between alcohol molecules and water molecules, small molecular mass alcohols have unlimited solubility in water. Alcohols, Phenols, and Ethers cont’d

17. Copyright © Houghton Mifflin Company. All rights reserved.14 | 17 ←Fig. 14.12 In an intramolecular alcohol dehydration the components of water are removed from neighboring carbon atoms. Alcohols, Phenols, and Ethers cont’d

18. Copyright © Houghton Mifflin Company. All rights reserved.14 | 18 →Fig. 14.13 The oxidation of ethanol is the basis for the “breathalyzer test.” Alcohols, Phenols, and Ethers cont’d

19. Copyright © Houghton Mifflin Company. All rights reserved.14 | 19 Alcohols, Phenols, and Ethers cont’d  CAG 14.1

20. Copyright © Houghton Mifflin Company. All rights reserved.14 | 20 →Fig. 14.14 Phenol molecule Alcohols, Phenols, and Ethers cont’d

21. Copyright © Houghton Mifflin Company. All rights reserved.14 | 21 →Fig. 14.15 Many commercially baked goods contain the antioxidants BHA and BHT to help prevent spoilage. Alcohols, Phenols, and Ethers cont’d © Henryk T. Kaiser/Envision

22. Copyright © Houghton Mifflin Company. All rights reserved.14 | 22 ←Fig. 14.16 Nutmeg tree fruit. A phenolic compound, isoeugenol, is responsible for the odor associated with nutmeg. Alcohols, Phenols, and Ethers cont’d © Michael Viard/Peter Arnold, Inc.

23. Copyright © Houghton Mifflin Company. All rights reserved.14 | 23 →Fig. 14.17 The similar shapes of water and dimethyl ether molecules. Alcohols, Phenols, and Ethers cont’d

24. Copyright © Houghton Mifflin Company. All rights reserved.14 | 24 ←Fig. 14.18 Alcohols and ethers with the same number of carbon atoms and the same degree of saturation are structural isomers. Alcohols, Phenols, and Ethers cont’d

25. Copyright © Houghton Mifflin Company. All rights reserved.14 | 25 Alcohols, Phenols, and Ethers cont’d © SIU/Peter Arnold, Inc.  CC 14.2

26. Copyright © Houghton Mifflin Company. All rights reserved.14 | 26 →Fig. 14.19 A physical-state summary for unbranched alkyl ethers at room temperature and pressure. Alcohols, Phenols, and Ethers cont’d

27. Copyright © Houghton Mifflin Company. All rights reserved.14 | 27 ←Fig. 14.20 Although ether molecules cannot hydrogen bond to one another, they can hydrogen bond to water molecules. Alcohols, Phenols, and Ethers cont’d

28. Copyright © Houghton Mifflin Company. All rights reserved.14 | 28 CC 14.3 Marijuana Alcohols, Phenols, and Ethers cont’d

29. Copyright © Houghton Mifflin Company. All rights reserved.14 | 29 →Fig. 14.21 Thiols are responsible for the strong odor of "essence of skunk." Alcohols, Phenols, and Ethers cont’d Jeff Lepore/Photo Researchers

30. Copyright © Houghton Mifflin Company. All rights reserved.14 | 30 Table 14.4 Alcohols, Phenols, and Ethers cont’d

31. Copyright © Houghton Mifflin Company. All rights reserved.14 | 31 ←Fig. 14.22 A comparison involving dimethyl ether and demethyl sulfide. Alcohols, Phenols, and Ethers cont’d

32. Copyright © Houghton Mifflin Company. All rights reserved.14 | 32 Alcohols, Phenols, and Ethers cont’d Getty Images CC 14.4