1. Chapter 22(a) Organic and Biological Molecules

2. Figure 22.1: The C—H bonds in methane.

3. Figure 22.2: (a) The Lewis structure of ethane (C 2 H 6 ). (b) The molecular structure of ethane represented by space-filling and ball-and-stick models.

4. Copyright © Houghton Mifflin Company. All rights reserved.22a–4 Figure 22.3: The structures of (a) propane (CH 3 CH 2 CH 3 ) and (b) butane (CH 3 CH 2 CH 2 CH 3 ). Each angle shown in red is 109.5º.

5. Copyright © Houghton Mifflin Company. All rights reserved.22a–5

6. Copyright © Houghton Mifflin Company. All rights reserved.22a–6 Figure 22.4: (a) Normal butane (abbreviated n-butane). (b) The branched isomer of butane (called isobutane).

7. Copyright © Houghton Mifflin Company. All rights reserved.22a–7 Normal pentane.

8. Copyright © Houghton Mifflin Company. All rights reserved.22a–8

9. Figure 22.5: (a) The molecular structure of cyclopropane (C 3 H 6 ). (b) The overlap of the sp 3 orbitals that form the C—C bonds in cyclopropane.

10. Figure 22.6: The (a) chair and (b) boat forms of cyclohexane.

11. Copyright © Houghton Mifflin Company. All rights reserved.22a–11 Figure 22.7: The bonding in ethylene.

12. Copyright © Houghton Mifflin Company. All rights reserved.22a–12 Figure 22.8: The bonding in ethane.

13. Figure 22.9: The two stereoisomers of 2-butene: (a) cis-2- butene and (b) trans-2- butene.

14. Copyright © Houghton Mifflin Company. All rights reserved.22a–14 Figure 22.10: The bonding in acetylene.

15. Copyright © Houghton Mifflin Company. All rights reserved.22a–15 Figure 22.11: (a) The structure of benzene, a planar ring system in which all bond angles are 120º. (b) Two of the resonance structures of benzene. (c) The usual representation of benzene.

16. Figure 22.12: Some selected substituted benzenes and their names. Common names are given in parentheses.

17. Copyright © Houghton Mifflin Company. All rights reserved.22a–17

18. Chapter 22(b) Organic and Biological Molecules (cont’d)

19. Copyright © Houghton Mifflin Company. All rights reserved.22a–19

20. Copyright © Houghton Mifflin Company. All rights reserved.22a–20

21. Copyright © Houghton Mifflin Company. All rights reserved.22a–21 Figure 22.13: Some common ketones and aldehydes.

22. Figure 22.14: Some carboxylic acids.

23. Figure 22.15: The general formulas for primary, secondary, and tertiary amines. R, R', and R" represent carbon-containing substituents.

24. Copyright © Houghton Mifflin Company. All rights reserved.22a–24

25. Copyright © Houghton Mifflin Company. All rights reserved.22a–25 A radio from the 1930’s made of Bakelite.

26. Copyright © Houghton Mifflin Company. All rights reserved.22a–26 A scanning electron microscope image showing the fractured plane of a self-healing material with a ruptured microcapsule in a thermosetting matrix.

27. Copyright © Houghton Mifflin Company. All rights reserved.22a–27

28. Copyright © Houghton Mifflin Company. All rights reserved.22a–28 Figure 22.16: The reaction to form nylon can be carried out at the interface of two immiscible liquid layers in a beaker. The bottom layer contains adipoyl chloride, dissolved in CCl 4, and the top layer contains hexamethylenediamine, dissolved in water. A molecule of HCl is formed as each C—N bond forms.

29. Copyright © Houghton Mifflin Company. All rights reserved.22a–29 Wallace H. Carothers

30. Copyright © Houghton Mifflin Company. All rights reserved.22a–30 Figure 22.17: (a) A tube composed of HDPE is inserted into the mold (die). (b) The die closes, sealing the bottom of the tube. (c) Compressed air is forced into the warm HDPE tube, which then expands to take the shape of the die. (d) The molded bottle is removed from the die.

31. Copyright © Houghton Mifflin Company. All rights reserved.22a–31 Figure 22.18: The 20 a-amino acids found in most proteins. The R group is shown in color.

32. Copyright © Houghton Mifflin Company. All rights reserved.22a–32 Figure 22.18 (cont’d)

33. Copyright © Houghton Mifflin Company. All rights reserved.22a–33 Figure 22.19: The amino acid sequences in (a) oxytocin and (b) vasopressin. The differing amino acids are boxed.

34. Figure 22.20: Hydrogen bonding within a protein chain causes it to form a stable helical structure called the  -helix. Only the main atoms in the helical backbone are shown here. The hydrogen bonds are not shown.

35. Chapter 22(c) Organic and Biological Molecules (cont’d)

36. Figure 22.21: Ball-and-stick model of a portion of a protein chain in the  -helical arrangement, showing the hydrogen- bonding interactions.

37. Copyright © Houghton Mifflin Company. All rights reserved.22a–37 Figure 22.22: When hydrogen bonding occurs between protein chains rather than within them, a stable structure (the pleated sheet) results.

38. Copyright © Houghton Mifflin Company. All rights reserved.22a–38 Figure 22.23: (a) Collagen, a protein found in tendons, consists of three protein chains. (b) The pleated-sheet arrangement of many proteins bound together to form the elongated protein found in silk fibers.

39. Copyright © Houghton Mifflin Company. All rights reserved.22a–39 Figure 22.24: Summary of the various types of interactions that stabilize the tertiary structure of a protein: (a) ionic, (b) hydrogen bonding, (c) covalent, (d) London dispersion, and (e) dipole–dipole.

40. Figure 22.25: The permanent waving of hair.

41. Copyright © Houghton Mifflin Company. All rights reserved.22a–41

42. Figure 22.26: A schematic representation of the thermal denaturation of a protein.

43. Figure 22.27: When a tetrahedral carbon atom has four different substituents, there is no way that its mirror image can be superimposed.

44. Copyright © Houghton Mifflin Company. All rights reserved.22a–44 Figure 22.28: The mirror image optical isomers of glyceraldehyde.

45. Figure 22.29: The cyclization of D -fructose.

46. Copyright © Houghton Mifflin Company. All rights reserved.22a–46 Figure 22.30: The cyclization of glucose. Two different rings are possible; they differ in the orientation of the hydroxy group and hydrogen on one carbon, as indicated. The two forms are designated  and  and are shown here in two representations.

47. Copyright © Houghton Mifflin Company. All rights reserved.22a–47 Figure 22.31: Sucrose is a disaccharide formed from  - D -glucose and fructose.

48. Copyright © Houghton Mifflin Company. All rights reserved.22a–48 Figure 22.32: (a) The polymer amylose is a major component of starch and is made up of  - D -glucose monomers.(b) The polymer cellulose, which consists of  - D -glucose monomers.

49. Figure 22.33: The structure of the pentoses (a) deoxyribose and (b) ribose.

50. Copyright © Houghton Mifflin Company. All rights reserved.22a–50 Figure 22.34: The organic bases found in DNA and RNA.

51. Copyright © Houghton Mifflin Company. All rights reserved.22a–51 Figure 22.35: (a) Adenosine is formed by the reaction of adenine with ribose. (b) The reaction of phosphoric acid with adenosine to form the ester adenosine 5-phosphoric acid, a nucleotide.

52. Figure 22.36: A portion of a typical nucleic acid chain. Note that the backbone consists of sugar– phosphate esters.

53. Copyright © Houghton Mifflin Company. All rights reserved.22a–53 Figure 22.37: (a) The DNA double helix contains two sugar–phosphate backbones, with the bases from the two strands hydrogen-bonded to each other. The complementarity of the (b) thymine-adenine and (c) cytosine-guanine pairs.

54. Figure 22.38: During cell division the original DNA double helix unwinds and new complementary strands are constructed on each original strand.

55. Copyright © Houghton Mifflin Company. All rights reserved.22a–55 Figure 22.39: The mRNA molecule, constructed from a specific gene on the DNA, is used as the pattern to construct a given protein with the assistance of ribosomes.