What are Alkenes and Alkynes?

Contributed by:

Jonathan James Mon, Jan 17, 2022 06:23 PM UTC

The highlights are:

A. Electrophilic Additions to Alkenes
1. Hydrohalogenation
2. Halogenation
3. Halohydrins
4. Hydration

B. Electrophilic Additions to Alkynes
1. Hydrohalogenation
2. Halogenation
3. Halohydrins
4. Hydration

C. Carbenes

1. p. 251

2. Alkenes & Alkynes
I. Prepapration of alkenes
1. Dehydrohalogenation
2. Dehydration

3. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
1. Hydrohalogenation
2. Halogenation
3. Halohydrins
4. Hydration

4. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
1. Hydrohalogenation (Chapter 7)

5. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
2. Halogenation

6. Electrophilic addition of Br2 to an alkene

7. p. 217

8. p. 218

9. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
2. Halogenation (working backwards)
H CH3
CH2CH 3 What alkene was
Cl the prodcut made from ?
H Cl

10. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
3. Halohydrins
Br 2
H2O

11. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
4. Hydration
i. acid catalyzed
H2SO 4 (cat)
H2O, 

12. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
4. Hydration
ii. oxymercurication

13. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
A. Electrophilic Additions to Alkenes
4. Hydration
iii. Hydroboration & oxidation
1. BH 3:THF
2. H2O2, OH

14. p. 223

15. +

-
+
-

Fig. 7-4, p. 225

16.

17. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
B. Electrophilic Additions to Alkynes
1. Hydrohalogenation (Chapter 7)
2. Halogenation
3. Halohydrins
4. Hydration

18. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
B. Electrophilic Additions to Alkynes
3. Halohydrins
Cl2
C C H
H2O

19. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
B. Electrophilic Additions to Alkynes
4. Hydration
i. acid catalyzed
H2SO 4 (cat)
C C H
H2O, 

20. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
B. Electrophilic Additions to Alkynes
4. Hydration
ii. oxymercuration

21. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
B. Electrophilic Additions to Alkynes
4. Hydration
ii. Hydroboratoin & oxidation
1. BH3:THF
CH3 C C H
2. H 2O 2, OH

22. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
C. Reductions
1. Alkenes
i. Catalytic hydrogenation

23. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
C. Reductions
2. Alkynes
i. Catalytic hydrogenation
a. Complete reduction

24. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
C. Reductions
2. Alkynes
i. Catalytic hydrogenation
ii. Lindlar’s catalyst (partial reduction)

25. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
C. Reductions
2. Alkynes
iii. Dissolving metal reduction (partial reduction)

26. H R
Na
R R
NH 3 R H

27. H R
Na
R R
NH 3 R H

28. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
D. Alkyne alkylation
1. NaNH2
H C C H
2. CH3I

29. Fig. 8-19, p. 292

30. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
E. Carbene addition

31. Fig. 7-6, p. 228

32.

33. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Oxidations
Introduction

34. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
E. Oxidations
1. epoxidation
i. Peracids (RCO3H)

35. Epoxide formation through reaction of peracids

36. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Oxidations
1. epoxidation
ii. via halohydrins

37. The Nobel Prize in Chemistry 2001
"for their work on chirally catalysed "for his work on chirally
hydrogenation reactions" catalysed oxidation reactions"
William S. Knowles Ryoji Noyori K. Barry Sharpless

38. Thalidomide
O O H O O H
N N
N (R) O N (S) O
H H
O O
 Racemic thalidomide prescribed for morning sickness (1956 – 1961)
 (R)-enantiomer is an antiemetic
 (S)-enantiomer is a teratogen

39. Sharpless epoxidation
Ti
HO OH
H CH3CH2O2C H H
H CO2CH2CH3 O
H H
H H
(CH
(CH 3)3COOH
3)3CCOOH
CH2OH CH2OH
95 % R
(+ 5 % S)

40. Knowles Asymmetric
Reduction
H H H
H2
CH3O CO2H Rh(DiPAMP) CH3O CO2H
NHR H NHR
RO RO
O
OCH3 97.5 % S
R = C CH3 (+ 2.5 % R)
P P
CH3O
(R,R)-DiPAMP

41. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Oxidations
2. dihydroxylation
i. osmium tetraoxide
1. OsO 4
2. NaHSO3

42. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
E. Oxidations
2. dihydroxylation
ii. from epoxides
H+
H 2O
H H
O

43. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Oxidations
2. Dihydroxylation
Application : Synthesis
H CH 3
OH H C C H
H OH

44. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
E. Oxidations
3. oxidative cleavage
i. ozonolysis
1. O3
2. Zn, CH3CO2H

45. p. 237

46. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
E. Oxidations
3. oxidative cleavage
i. ozonolysis
1. O3
2. Zn, CH3CO2H
1. O3
2. Zn, CH3CO2H
1. O3
2. Zn, CH3CO2H

47. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Oxidations
3. oxidative cleavage
ii. permanganate
KMnO 4
H +, H2O, 

48. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Oxidations
3. oxidative cleavage
iii. from diols

49. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
G. Conjugated Dienes
Introduction

50. Fig. 8-12, p. 281

51. Fig. 8-13, p. 282

52. Fig. 8-14, p. 282

53. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
G. Conjugated Dienes
1. Addition of HX

54. Reaction energy diagram for addition of HBr to butadiene

55. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
G. Conjugated Dienes
2. The Diels-Alder reaction
Introduction
a. the overall reaction
b. history
c. nature of the diene and dienophile
d. the molecular orbital picture
e. conformation of the diene

56. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Conjugated Dienes
2. The Diels-Alder reaction
Introduction
a. the overall reaction

57. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
G. Conjugated Dienes
2. The Diels-Alder reaction
Introduction
b. history
Albrecht reaction
Liebigs 1906, 348, 31.
Staudinger, H.; Bruson, H. A.
Liebigs 1926 , 446 , 97.
Diels, O.; Alder, K.
Liebigs. 1928, 460, 98.
Nobel Prize 1950

58. The Nobel Prize in Chemistry 1950
"for their discovery and development of the diene synthesis "
Otto Paul Hermann Diels Kurt Alder

59. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
G. Conjugated Dienes
2. The Diels-Alder reaction
Introduction
c. nature of the diene and dienophile

60. p. 286

61. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Conjugated Dienes
2. The Diels-Alder reaction
Introduction
d. the molecular orbital picture

62. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Conjugated Dienes
2. The Diels-Alder reaction
Introduction
e. the diene conformation

63. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Conjugated Dienes
2. The Diels-Alder reaction
Stereochemistry (Alder’s Endo Rule)

64. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Conjugated Dienes
2. The Diels-Alder reaction
Regiochemistry (The Ortho Rule)

65. Alkenes & Alkynes
II. Reactions of alkenes & alkynes
F. Conjugated Dienes
2. The Diels-Alder reaction
Regiochemistry (The Para Rule)

66. Fig. 8-17, p. 287

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