1. Page: 287

2. Page: 287
The gases released during volcanic eruptions contain large amounts of organohalides, including chloromethane, chloroform, dichlorodifluoromethane, and many others.

3. Page: 288

4. Page: 288

5. Page: 288

6. Page: 288

7. Page: 289

8. Page: 289

9. Page: 289

10. Page: 290
FIGURE 10-1 Mechanism of the radical chlorination of methane. Three kinds of steps are required: initiation, propagation, and termination. The propagation steps are a repeating cycle, with Cl· a reactant in step 1 and a product in step 2, and with ·CH3 a product in step 1 and a reactant in step 2. (The symbol hv shown in the initiation step is the standard way of indicating irradiation with light.)

11. Page: 290

12. Page: 291

13. Page: 291

14. Page: 291

15. Page: 292

16. Page: 292

17. Page: 293
FIGURE 10-2 Mechanism of allylic bromination of an alkene with NBS. The process is a radical chain reaction in which (1) a Br· radical abstracts an allylic hydrogen atom of the alkene and gives an allylic radical plus HBr. (2) The HBr then reacts with NBS to form Br2, which (3) reacts with the allylic radical to yield the bromoalkene product and a Br· radical that continues the chain.

18. Page: 293

19. Page: 293

20. Page: 294
FIGURE 10-3 An orbital view of the allyl radical. The p orbital on the central carbon can overlap equally well with a p orbital on either neighboring carbon, giving rise to two equivalent resonance structures.

21. Page: 294

22. Page: 294

23. Page: 295
FIGURE 10-4 The spin density surface of the allyl radical locates the position of the unpaired electron and shows that it is equally shared between the two terminal carbons.

24. Page: 295

25. Page: 296

26. Page: 296

27. Page: 296

28. Page: 297

29. Page: 297

30. Page: 297

31. Page: 297

32. Page: 298

33. Page: 298

34. Page: 298

35. Page: 299

36. Page: 299

37. Page: 299

38. Page: 300

39. Page: 300

40. Page: 300

41. Page: 300

42. Page: 301

43. Page: 301

44. Page: 301

45. Page: 302
FIGURE 10-5 Mechanism of the Suzuki–Miyaura coupling reaction of an aromatic boronic acid with an aromatic halide to give a biaryl. The reaction takes place by (1) reaction of the aromatic halide, ArX, with the catalyst to form an organopalladium intermediate, followed by (2) reaction with the aromatic boronic acid. (3) Subsequent decomposition of the diarylpalladium intermediate gives the biaryl product.

46. Page: 302

47. Page: 302

48. Page: 303

49. Page: 303

50. Page: 304
FIGURE 10-6 Oxidation levels of some common types of compounds.

51. Page: 304

52. Page: 304

53. Page: 305

54. Page: 305

55. Page: 305

56. Page: 306
Marine corals secrete organohalogen compounds that act as a feeding deterrent to fish.

57. Page: 306

58. Page: 307

59. Page: 307

60. Page: 307

61. Page: 308

62. Page: 308

63. Page: 308

64. Page: 308

65. Page: 308

66. Page: 308

67. Page: 308

68. Page: 308

69. Page: 308a

70. Page: 308a

71. Page: 308a

72. Page: 308b

73. Page: 308b

74. Page: 308b

75. Page: 308b

76. Page: 308c

77. Page: 308d

78. Page: 308d

79. Page: 308d

80. Page: 308d

81. Page: 308e

82. Page: 308e

83. Page: 308e

84. Page: 308e

85. Page: 308f

86. Page: 308f

87. Page: 308f

88. Page: 308f

89. Page: 308f

90. Page: 308g

91. Page: 308g

92. Page: 308g

93. Page: 308h

94. Page: 308h