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1559Tch16291-30311/3/0510:02Page303 Soutionsto Problems303 52.The electrophile :6=N-:2m:6=N-9-0628一:6=N Nitrosonium ion Th 5-5-6- 0记-0 Ga o-ac6- Friedel-Crafts ⊙-80- 54.@ 55.0 56. 57. 58.(dSolutions to Problems • 303 However, the ONO group is inductively electron withdrawing. As is the case with halogen substituents, this deactivating inductive effect is on the average stronger than the resonance effect, so nitrosobenzene is deacti￾vated overall, even though substitution is preferred (by the resonance effect) at the ortho and para positions. 52. The electrophile: Then and 53. At this point the system has two options: add another styrene and proceed with polymerization, or close a ring by intramolecular Friedel-Crafts reaction. Polymerization: Friedel-Crafts: 54. (c) 55. (b) 56. (c) 57. (c) 58. (d) H H A etc. H H OH NO OH H NO OH NO H OH OH NO N O OH H N O 2H H2O OH2 O N  O O N O N O Nitrosonium ion N 1559T_ch16_291-303 11/3/05 10:02 Page 303
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