1. Buha Harnish
Chemical Engineer

2. Nitration of Methyl Benzoate

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

4. Ortho Meta Para
Ortho
Meta
Para

5. Nomenclature 6 2 3 5 4

6. Nucleophilic Aliphatic Substitution
Electrophilic Aromatic Substitution

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

8. Mechanism
E - Y

9. E - Y
Mechanism
+ H+

10. Charge o and p

11. Reaction Coordinate

12. Nitration of Benzene
Nitrobenzene

13. Nitration Reagent
HONO H2SO4
NO H3O HSO4-
Nitronium Ion

15. Multiple SubstituentsG
Second Group. Where go? How fast?

16. Nitration of Toluene
HNO3
63% 3%
34%

17. ORTHO + + +
META + + +
PARA + + +

18. Electron donating groups favor reaction ORTHO and PARA.

19. Nitration of (trifluoromethyl)benzene
HNO3
H2SO4 6%
91% 3%

20. Electron Withdrawing group
+ charge here bad

21. Ortho + + +
Meta + + +
Para + + +

22. Electron Withdrawing Groups are Meta Directors and DEACTIVATING
Meta Product

23. Ortho-Para Directors
Very Activating
-NH2
-NHR
-OH
-OR O
-NHCR O
-OCR

24. Deactivating -Halogens Ortho-Para Directors Activating -R Activating

25. Meta Directors O
-SO3H
-CR O
-NO2
-COH
-CN

26. Main Reaction
meta
Side Products

27. Procedure 1. Dissolve methyl benzoate in H2SO4 2. Mix HNO3 and
H2SO4 at 0oC
3. Add HNO3 / H2SO4
dropwise to methyl
benzoate at 0oC

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

29. Filter

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