1. Dehydration of Alcohols

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

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

4. Leaving Group

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

8. E1
1 bond at a time
Elimination

9. R+
SN1 E1
Rearrangement
Substitution
Elimination

10. SN1 E1

11. Dehydrohalogenation X
C - C H
Strong base

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

13. Isotope Effect
NaOEt
NaOEt
kH/kD = 7

14. Isotope effect shows that C-H bond broken in the transition state.

15. Element Effect
Change Element
I > Br > Cl

16. SYN vs. ANTI Elimination
Same Side
Opposite Side

19. Transition State
Energy
Starting
Material
Product

20. E 2
2 Bonds at a time
Elimination

21. Procedure

22. Put cyclohexanol and sulfuric acid in round bottom flask
Fractional Distillation (steam distillation) collect distillate 80-85o
Dry product with K2CO3
4. Distill

23. Distil immiscible liquids
PT = PA PB
(Steam Distillation)

24. Baeyer Unsaturation Tests
Potassium Permanganate
KMnO4

27. Bromine and Cyclohexene