ChemActivity 29

ChemActivity 29 - Mark Biagi ChemActivity 29 Chem. 204-01...

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Mark Biagi ChemActivity 29 Chem. 204-01 13A. The pi system of the ring acts as a nucleophile in an EAS system. 13B. The more electron rich the pi system of the aromatic ring, the faster the rate of EAS. 14. Benzene will undergo EAS reactions faster than nitrobenzene because the nitro group stabilizes the carbocation intermediate, raises the energy of the transition state, and results in an overall decreased rate of the reaction. 15. The two nitro groups attached to benzene are such powerful electron withdrawing groups that they cause the carbocation intermediate to become so destabilized that the reaction would take place extremely slowly, no matter what electrophile is used. 16. The methyl group attached to benzene is an electron donating group and the nitro group is an electron withdrawing group. The nitrobenzene destabilizes the carbocation intermediate and any EAS reaction with nitrobenzene happens very slowly. On the other hand toluene stabilizes the carbocation intermediate which causes the EAS reaction to happen faster. In other words, the nitrobenzene takes so long to react
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ChemActivity 29 - Mark Biagi ChemActivity 29 Chem. 204-01...

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