chapter 10 review

1. Chapter 10
This PowerPoint can be found on Slideshare powered by Linkedin
Search “DanielEisenstein1”
If you find a “DanielEisenstein2” let me know so I can take care of the imposter

2. Alkenes
 C=C double bond
 Terminal alkene= on end
 Internal alkene= internal
 Pi bond<sigma bond

3. Degrees of unsaturation
 Method
 Step 1) find maximum number of hydrogens
Use formula CnHn+2
 Step 2) Find number of “Hydrogens”
Add number of halogens
Ignore oxygens
Substract number of N

4. Degrees of unsaturation (Continued)
 Step 3) (Step 1- step 2)/ 2
 Give number of pi bonds or cyclic structure

5. Practice

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

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

8. 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

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

10. Practice

11. Practice

12. Practice

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

14. practice

15. Preparation of alkenes

16. practice

17. Characteristics of Addition
 1 pi bond breaks
 2 sigma bonds form
 Syn periplanar vs. anti periplanar
 exothermic

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

19. Addition reactions

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

21. Practice

22. Acid-catalyzed hydration
 Mechanism
 Markovnikov
 Syn and anti addition

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. Hydroboration-Oxidation
 ANTI MARKOVNIKOV
 Due to large size of boron
 Mechanism
 Syn addition only

29. Practice

30. Practice