1. Chapter Thirteen Unsaturated Hydrocarbons

2. Copyright © Houghton Mifflin Company. All rights reserved.13 | 2 Junebug Clark/Photo Researchers Unsaturated Hydrocarbons  CO 13.1

3. Copyright © Houghton Mifflin Company. All rights reserved.13 | 3 →Fig. 13.1 In ethene, the atoms are in a flat rather than a tetrahedral arrangement. Unsaturated Hydrocarbons cont’d

4. Copyright © Houghton Mifflin Company. All rights reserved.13 | 4 ←CC 13.1 Ethene is the hormone that causes tomatoes to ripen. Unsaturated Hydrocarbons cont’d Alan Detrick/Photo Researchers

5. Copyright © Houghton Mifflin Company. All rights reserved.13 | 5 Fig. 13.2 A comparison of structural isomerism possibilities for four and five-carbon alkane and alkene systems. Unsaturated Hydrocarbons cont’d

6. Copyright © Houghton Mifflin Company. All rights reserved.13 | 6 ←Fig. 13.3 Cis-trans isomers: Different representatives of the cis and trans isomers of 2- butene. Unsaturated Hydrocarbons cont’d

7. Copyright © Houghton Mifflin Company. All rights reserved.13 | 7 Unsaturated Hydrocarbons cont’d  CC 13.2

8. Copyright © Houghton Mifflin Company. All rights reserved.13 | 8 →Fig. 13.4 The application of sex pheromones in insect control involves using a small amount of synthetically produced pheromone to lure a particular insect into a trap. Unsaturated Hydrocarbons cont’d Donald C. Booth/Color-Pic

9. Copyright © Houghton Mifflin Company. All rights reserved.13 | 9 ←Fig. 13.5 Selected terpenes containing two, three, and eight isoprene units. Unsaturated Hydrocarbons cont’d

10. Copyright © Houghton Mifflin Company. All rights reserved.13 | 10 →Fig. 13.6 The molecule Beta- carotene is responsible for the yellow-orange color of carrots, apricots, and yams. Unsaturated Hydrocarbons cont’d © Martha Cooper/Peter Arnold, Inc.

11. Copyright © Houghton Mifflin Company. All rights reserved.13 | 11 ←Fig. 13.7 A physical-state summary for unbranched 1-alkenes and unsubstituted cycloalkenes with one double bond at room temperature and pressure. Unsaturated Hydrocarbons cont’d

12. Copyright © Houghton Mifflin Company. All rights reserved.13 | 12 →Fig. 13.8 In an alkene addition, reaction, the atoms provided by an incoming molecule are attached to the carbon atoms originally joined by a double bond. In the process, the double bond becomes a single bond. Unsaturated Hydrocarbons cont’d

13. Copyright © Houghton Mifflin Company. All rights reserved.13 | 13 ←CC 13.3 Carotenoids, molecules that contain eight isoprene units, are responsible for the yellow- orange color of autumn leaves. Unsaturated Hydrocarbons cont’d PhotoDisc

14. Copyright © Houghton Mifflin Company. All rights reserved.13 | 14 →Fig. 13.9 A bromine in water solution is reddish brown. When a small amount of such a solution is added to an unsaturated hydrocarbon, the added solution is decolorized. Unsaturated Hydrocarbons cont’d

15. Copyright © Houghton Mifflin Company. All rights reserved.13 | 15 ←Fig. 13.10 Vladimir Markovnikov synthesized rings containing four carbon atoms and seven carbon atoms. Unsaturated Hydrocarbons cont’d Edgar Fahs Smith Collection, University of Pennsylvania Library

16. Copyright © Houghton Mifflin Company. All rights reserved.13 | 16 →Fig. 13.11 Preparation of polystyrene. Unsaturated Hydrocarbons cont’d

17. Copyright © Houghton Mifflin Company. All rights reserved.13 | 17 Fig. 13.12 (a) polyethylene (b) polypropylene (c) poly (vinyl chloride) Unsaturated Hydrocarbons cont’d

18. Copyright © Houghton Mifflin Company. All rights reserved.13 | 18 →Fig. 13.13 Examples of objects made of polyethylene. Unsaturated Hydrocarbons cont’d

19. Copyright © Houghton Mifflin Company. All rights reserved.13 | 19 ←Fig. 13.14 Natural rubber being harvested in Malaysia. Unsaturated Hydrocarbons cont’d © Bill Stanton/Rainbow

20. Copyright © Houghton Mifflin Company. All rights reserved.13 | 20 Fig. 13.15 Ethyne, the simplest alkyne. Unsaturated Hydrocarbons cont’d

21. Copyright © Houghton Mifflin Company. All rights reserved.13 | 21 Unsaturated Hydrocarbons cont’d CAG 13.1

22. Copyright © Houghton Mifflin Company. All rights reserved.13 | 22 ←Fig. 13.16 Physical state summary for unbranched 1 alkynes at room temperature and pressure. Unsaturated Hydrocarbons cont’d

23. Copyright © Houghton Mifflin Company. All rights reserved.13 | 23 Unsaturated Hydrocarbons cont’d  CAG 13.2

24. Copyright © Houghton Mifflin Company. All rights reserved.13 | 24 →Fig. 13.17 Space-filling and ball- and-stick models for the structure of benzene. Unsaturated Hydrocarbons cont’d

25. Copyright © Houghton Mifflin Company. All rights reserved.13 | 25 →Fig. 13.18 2-chlorotoluene molecule Unsaturated Hydrocarbons cont’d

26. Copyright © Houghton Mifflin Company. All rights reserved.13 | 26 →CC 13. 4 Unsaturated Hydrocarbons cont’d