If you are in my fall 2021 class, this is the file you download

1. Chapter 8
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2. Nomenclature
 Replace –ane with –ene
 Put number before –ene
 Use first number on C=C to name
 Under alcohol in priority

3. Nomenclature (continued)
 WE DON’T NUMBER THE alkene on the
[REDACTED] RING
 *unless there is alcohol
 2 C=C diene
 3 C=C triene

6. EZ system
 Use if there are 3 or 4 different groups
 Steps
 1) assign priorities (same as R/S naming)
 2)designate as E or Z

7. EZ system: E vs. Z
 E means high groups on opposite sides
 Z means high groups are on same side

8. Practice

9. Practice

10. Practice

11. Physical properties
 Van Der Waals
 Nothing special
 Cis is slightly polar

12. practice

14. practice

15. Characteristics of Addition
 1 pi bond breaks
 2 sigma bonds form
 Syn periplanar vs. anti periplanar
 Exothermic-discuss!

16. Markovnikov’s rule
 We want more stable carbocation
 H adds to least substituted side
 Nu: adds to more substituted side

17. Hydrohalogenation
 Mechanism
 Carbocation formation= rate-determining step
 Stereochemistry= racemic; syn and anti
 Markovnikov

18. Practice

19. Acid-catalyzed hydration
 Very similar to hydrohalogenation
 Mechanism
 Markovnikov
 Syn and anti addition

20. Practice

21. Oxymercuration-Demercuration
 Don’t worry about the mechanism
 MOST IMPORTANT THING= no carbocation
intermediate
 But it is still Markovnikov

22. Hydroboration-Oxidation
 ANTI MARKOVNIKOV
 Due to large size of boron
 Syn addition only
 Don’t worry about the mech

23. Practice

24. Halogenation
 X=Cl or Br
 MY FAVORITE MECHANISM
 Anti addition

25. practice

26. Halohydrin Formation
 Reagents= X2 and H2O
 Anti periplanar addition
 Preferred product has X on less substituted carbon
 Water bonds to more substituted carbon
 Mechanism

27. practice

28. Practice

29. Dihydroxylation
 Everything is on the wheel
 No mech= no worries