1. Nitration of Methyl Benzoate

2. A B C 50% Yield =25% Multistep Synthesis

3. Ortho Meta Para Ortho Meta Para

4. 2 3 4 5 6 Number Ring

5. Nucleophilic Aliphatic Substitution Electrophilic Aromatic Substitution

6. E+E+ + H + The electrophile REPLACES H + ARENE SUBSTITUTION

7. E - Y Mechanism

8. E - Y + H + Mechanism

9. Charge o and p

10. Energy Diagram

11. Nitrobenzene Nitration of Benzene

12. Nitronium Ion HONO 2 + 2 H 2 SO 4 NO 2 + + H 3 O + + 2 HSO 4 - Nitration Reagent

13. Nitration Mechanism

14. G Second Group. Where go? How fast? Multiple Substituents

15. HNO 3 63% 3% 34% Nitration of Toluene

16. + ++ + + + + + + ORTHO META PARA Compare o, m, p

17. Favor: ORTHO and PARA. Electron Donating Ortho Para Electron Donating Groups

18. HNO 3 H 2 SO 4 6% 91% 3% Nitration of trifluoromethylbenzene

19. + charge here bad Electron Withdrawing Groups

20. Ortho Meta Para + ++ + + + + + + Compare o, m, p

21. Meta Directors and DEACTIVATING Electron Withdrawing Group Meta Product Electron Withdrawing Groups

22. -NH 2 -OH -NHR -OR -OCR -NHCR O O Very Activating Ortho-Para Directors

23. -R -Ar -Halogens Activating Deactivating Ortho-Para Directors

24. -CR O -COH O -CN -SO 3 H -NO 2 Meta Directors

25. Side Products meta Main Reaction

26. 1. Dissolve methyl benzoate in H 2 SO 4 2. Mix HNO 3 and H 2 SO 4 at 0 o C 3. Add HNO 3 / H 2 SO 4 dropwise to methyl benzoate at 0 o C Procedure

27. 4. Let stand at room temperature 10 minutes 5. Pour onto ice Procedure

28. Filter

29. Recrystallize from methanol Dry Weigh m.p. Wash