1. Dehydration of Alcohols

2. C - C X Y To make C=C need to eliminate X, Y. Elimination Reactions

3. C - C X Y 1. Concerted (x and y leave same time) 2. X leaves first 3. Y leaves first 3 ways to break 2 bonds

4. Leaving Group

5. Mechanism

7. R-XR + + X - Alkene + H + E1 Reaction

8. Elimination 1 bond at a time E1

9. Substitution Elimination Rearrangement SN1SN1 E1 R+R+

10. SN1SN1 E1 SN1

11. C - C X H Strong base Dehydrohalogenation

12. What is the mechanism of dehydrohalogentation? C-D bond stronger than C-H bond. Isotope Effects

13. NaOEt k H /k D = 7 Isotope Effect

14. Isotope effect shows that C-H bond broken in the transition state. Bond Broken in Transition State

15. Change Element I > Br > Cl Element Effect

16. Same Side Opposite Side SYN vs. ANTI Elimination

18. E2 Animation

19. Product Starting Material Energy Transition State

20. Elimination 2 Bonds at a time E 2

21. Procedure

22. Put cyclohexanol and sulfuric acid in round bottom flask Fractional Distillation (steam distillation) collect distillate 80-85o Procedure

23. Dry product with K 2 CO 3

24. Distill

25. P T = P A + P B (Steam Distillation) Distil immiscible liquids

26. Potassium Permanganate KMnO 4 Baeyer Unsaturation Tests

28. Bromine Addition

29. Bromine and Cyclohexene

30. Br + - - + Bromonium Ion

31. Bromonium Ion Intermediate

32. Br - Mechanism

33. Animation