1. Organic Chemistry, 7e by L. G. Wade, Jr. Chapter 8 Reactions of Alkenes Christine Hermann Radford University Radford, VA Copyright © 2010 Pearson Education, Inc.

2. 8.1 a.BrCH 2 CH 2 CH 3 b.BrCH 2 CH(Br)CH 3 c.CH 3 CH(Br)CH 3 d.CH 3 CH(OH)CH 3

3. 8.1 Answer a.BrCH 2 CH 2 CH 3 b.BrCH 2 CH(Br)CH 3 c.CH 3 CH(Br)CH 3 d.CH 3 CH(OH)CH 3 H adds to the least substituted carbon.

4. 8.2 a.BrCH 2 CH 2 CH 3 b.BrCH 2 CH(Br)CH 3 c.CH 3 CH(Br)CH 3 d.CH 3 CH(OH)CH 3

5. 8.2 Answer a.BrCH 2 CH 2 CH 3 b.BrCH 2 CH(Br)CH 3 c.CH 3 CH(Br)CH 3 d.CH 3 CH(OH)CH 3 Br adds to the least substituted carbon.

6. 8.3 Identify the intermediate in the reaction of an alkene with hydrogen peroxide and HBr. a.Anion b.Cation c.Radical d.Cycloalkane

7. 8.3 Answer a.Anion b.Cation c.Radical d.Cycloalkane In the reaction of an alkene with hydrogen peroxide and HBr, a radical is the intermediate.

8. 8.4 a.HOCH 2 CH 2 CH 3 b.CH 2 =CHCH 3 c.HOCH 2 CH(OH)CH 3 d.CH 3 CH(OH)CH 3

9. 8.4 Answer a.HOCH 2 CH 2 CH 3 b.CH 2 =CHCH 3 c.HOCH 2 CH(OH)CH 3 d.CH 3 CH(OH)CH 3 H adds to the least substituted carbon.

10. 8.5 Give the intermediate for the dehydration of 2-methyl-2- butanol. a.Methyl carbocation b.Primary carbocation c.Secondary carbocation d.Tertiary carbocation

11. 8.5 Answer a.Methyl carbocation b.Primary carbocation c.Secondary carbocation d.Tertiary carbocation A tertiary carbocation is formed in the dehydration of 2-methyl-2-butanol.

12. 8.6 a.HOCH 2 CH 2 CH 3 b.CH 3 CH(OH)CH 3 c.CH 2 =CHCH 3 d.HOCH 2 CH(OH)CH 3

13. 8.6 Answer a.HOCH 2 CH 2 CH 3 b.CH 3 CH(OH)CH 3 c.CH 2 =CHCH 3 d.HOCH 2 CH(OH)CH 3 H adds to the least substituted carbon.

14. 8.7 a.CH 3 OCH 2 CH 2 CH 3 b.CH 3 CH(OCH 3 )CH 3 c.CH 2 =CHCH 3 d.CH 3 OCH 2 CH(OCH 3 )CH 3

15. 8.7 Answer a.CH 3 OCH 2 CH 2 CH 3 b.CH 3 CH(OCH 3 )CH 3 c.CH 2 =CHCH 3 d.CH 3 OCH 2 CH(OCH 3 )CH 3 H adds to the least substituted carbon.

16. 8.8 a.HOCH 2 CH 2 CH 3 b.CH 3 CH(OH)CH 3 c.CH 2 =CHCH 3 d.HOCH 2 CH(OH)CH 3

17. 8.8 Answer a.HOCH 2 CH 2 CH 3 b.CH 3 CH(OH)CH 3 c.CH 2 =CHCH 3 d.HOCH 2 CH(OH)CH 3 H adds to the most substituted carbon.

18. 8.9 Identify for the hydroboration of an alkene. a.Markovnikov, anti addition b.Markovnikov, syn addition c.Anti-Markovnikov, anti addition d.Anti-Markovnikov, syn addition e.None of the above

19. 8.9 Answer a.Markovnikov, anti addition b.Markovnikov, syn addition c.Anti-Markovnikov, anti addition d.Anti-Markovnikov, syn addition e.None of the above

20. 8.10 a.ClCH 2 CH 2 CH 3 b.CH 3 CH(Cl)CH 3 c.CH 3 CH 2 CH 3 d.ClCH 2 CH(Cl)CH 3

21. 8.10 Answer a.ClCH 2 CH 2 CH 3 b.CH 3 CH(Cl)CH 3 c.CH 3 CH 2 CH 3 d.ClCH 2 CH(Cl)CH 3 The Cl 2 adds across the double bond.

22. 8.11 Identify the intermediate in the halogenation of an alkene. a.Radical b.Anion c.Cation d.Halonium ion

23. 8.11 Answer a.Radical b.Anion c.Cation d.Halonium ion A three-membered ring, halonium ion, is the intermediate in the halogenation of an alkene.

24. 8.12 a.ClCH 2 CH(OH)CH 3 b.HOCH 2 CH(Cl)CH 3 c.ClCH 2 CH(Cl)CH 3 d.HOCH 2 CH(OH)CH 3

25. 8.12 Answer a.ClCH 2 CH(OH)CH 3 b.HOCH 2 CH(Cl)CH 3 c.ClCH 2 CH(Cl)CH 3 d.HOCH 2 CH(OH)CH 3 OH adds to the more substituted carbon.

26. 8.13 a.CH 3 CH 2 CH 2 CH 3 b.CH 3 CH 2 CH 3 c.CH 3 CH 3 d.HC≡CCH 3 e.HC≡CCH 2 CH 3

27. 8.13 Answer a.CH 3 CH 2 CH 2 CH 3 b.CH 3 CH 2 CH 3 c.CH 3 CH 3 d.HC≡CCH 3 e.HC≡CCH 2 CH 3 An alkane is made in the hydrogenation of an alkene.

28. 8.14 Identify the intermediate in the reaction of an alkene with diazomethane. a.Radical b.Anion c.Cation d.Carbene

29. 8.14 Answer a.Radical b.Anion c.Cation d.Carbene A carbene is the intermediate in the reaction of an alkene with diazomethane.

30. 8.15 a.Butane b.2-Methylpropane c.Methylcyclopropane d.Cyclopropane

31. 8.15 Answer a.Butane b.2-Methylpropane c.Methylcyclopropane d.Cyclopropane A cyclopropane is formed in this Simmons–Smith reaction.

32. 8.16 Identify the product in the reaction of an alkene with a peroxyacid. a.Cyclopropane b.Epoxide c.Alcohol d.Ether

33. 8.16 Answer a.Cyclopropane b.Epoxide c.Alcohol d.Ether An epoxide is formed in the reaction of an alkene with a peroxyacid.

34. 8.17 a.HOCH 2 CH 2 CH 3 b.CH 3 CH(OH)CH 3 c.HOCH 2 CH(OH)CH 3 d.HOCH 2 CH 2 CH 2 OH

35. 8.17 Answer a.HOCH 2 CH 2 CH 3 b.CH 3 CH(OH)CH 3 c.HOCH 2 CH(OH)CH 3 d.HOCH 2 CH 2 CH 2 OH Two OHs add across the double bond.

36. 8.18 Describe the addition of potassium permanganate to an alkene. a.Syn dihydroxylation b.Anti dihydroxylation c.Markovnikov addition of water d.Anti-Markovnikov addition of water

37. 8.18 Answer a.Syn dihydroxylation b.Anti dihydroxylation c.Markovnikov addition of water d.Anti-Markovnikov addition of water A five-membered ring is the intermediate.

38. 8.19 a.HOCH 2 CH(OH)CH 3 b.H 2 C=O + CH 3 CHO c.CO 2 + CH 3 COOH d.CO 2 + CH 3 CHO

39. 8.19 Answer a.HOCH 2 CH(OH)CH 3 b.H 2 C=O + CH 3 CHO c.CO 2 + CH 3 COOH d.CO 2 + CH 3 CHO Ozonolysis oxidizes alkenes to aldehydes and/or ketones.

40. 8.20 Identify the polymerization that is electrophilic addition. a.Anionic polymerization b.Free-radical polymerization c.Cationic polymerization d.None

41. 8.20 Answer a.Anionic polymerization b.Free-radical polymerization c.Cationic polymerization d.None