p Bonds as Nucleophiles

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1 Chapter 8 p Bonds as Nucleophiles REACTIONS OF ALKENES, ALKYNES, DIENES, AND ENOLS Copyright 2018 by Nelson Education Limited 1

2 8.2.1 Orbital structure of alkenes Geometry: Electrostatic potential: Electron-rich p bond can act as a nucleophile. Copyright 2018 by Nelson Education Limited 2

3 8.2.2 Electrophilic addition reactions Addition of hydrogen halides Copyright 2018 by Nelson Education Limited 3

4 Mechanism: Step 1: Step 2: Copyright 2018 by Nelson Education Limited 4

5 8.3 Carbocation Formation and Function Copyright 2018 by Nelson Education Limited 5

6 8.3.1 Energy changes control reactivity Copyright 2018 by Nelson Education Limited 6

7 8.3.2 Regioselectivity in electrophilic addition reactions Regioisomers: constitutional isomers formed when a reaction takes place at different locations in a molecule Regioselectivity: formation of one regioisomer in preference to others regioisomers major product Copyright 2018 by Nelson Education Limited 7

8 Carbocation formation is the rate-determining step. Copyright 2018 by Nelson Education Limited 8

9 Regioselectivity of electrophilic addition is controlled by carbocation stability. Copyright 2018 by Nelson Education Limited 9

10 8.3.3 Markovnikov s rule The major regioisomer product in an electrophilic addition is the one formed from the most stable carbocation. Copyright 2018 by Nelson Education Limited 10

11 8.3.4 Stability of carbocations Electrostatic potential maps for substituted carbocations: less stable more stable Greater degree of substitution results in greater positive charge dissipation (reduced intensity of blue regions) and more effective stabilization. Copyright 2018 by Nelson Education Limited 11

12 8.3.5 Stabilization of carbocations by hyperconjugation Hyperconjugation: electron donation from a s bond Copyright 2018 by Nelson Education Limited 12

13 8.3.6 Stabilization of carbocations by charge delocalization Carbocations are stabilized by electron-donating groups. Copyright 2018 by Nelson Education Limited 13

14 8.3.7 Applying the Hammond postulate Hammond postulate: the structure of a transition state resembles the species nearest to it in free energy Recall: Lower energy transition state faster reaction rate Copyright 2018 by Nelson Education Limited 14

15 Copyright 2018 by Nelson Education Limited 15

16 8.3.8 Reactions with carbocations are not stereoselective Copyright 2018 by Nelson Education Limited 16

17 8.4 Markovnikov Addition of Water to Alkenes Copyright 2018 by Nelson Education Limited 17

18 Copyright 2018 by Nelson Education Limited 18

19 Mechanism: Copyright 2018 by Nelson Education Limited 19

20 Mechanism (continued): (minor) (major) Copyright 2018 by Nelson Education Limited 20

21 Note the similarity in mechanism for addition of HBr vs H 2 O: Copyright 2018 by Nelson Education Limited 21

22 8.4.1 Addition of alcohols by acid catalysis Mechanism is essentially identical to addition of H 2 O. Copyright 2018 by Nelson Education Limited 22

23 8.4.2 Addition of water by oxymercuration-demurcuration Mild reaction conditions Formation of mercurium ion (occurs in a single step): Copyright 2018 by Nelson Education Limited 23

24 Mechanism: more stabilized transition state Copyright 2018 by Nelson Education Limited 24

25 Mechanism (continued): major minor The path that incorporates the more stabilized transition state (red) proceeds more quickly. Copyright 2018 by Nelson Education Limited 25

26 8.5 Carbocation Rearrangements Copyright 2018 by Nelson Education Limited 26

27 s bonds can relocate (shift) to generate more stable carbocation intermediates. Copyright 2018 by Nelson Education Limited 27

28 Shifts in systems stabilized by charge delocalization: Copyright 2018 by Nelson Education Limited 28

29 8.6 Addition of Halogens to Double Bonds Copyright 2018 by Nelson Education Limited 29

30 Charge separation in diatomic halogens: Mechanism (compare with oxymercuration): Copyright 2018 by Nelson Education Limited 30

31 Stereochemistry of halogenation: anti addition product Example: Copyright 2018 by Nelson Education Limited 31

32 8.6.1 Addition of hypohalous acids Mechanism (compare with halogenation and acid-catalyzed hydration): Copyright 2018 by Nelson Education Limited 32

33 Stereochemistry of hypohalous acid addition: Compare with halogenation. Copyright 2018 by Nelson Education Limited 33

34 8.7 Other Types of Electrophilic Additions Copyright 2018 by Nelson Education Limited 34

35 8.7.1 Epoxidation of alkenes mcpba = m-chloroperoxybenzoic acid Copyright 2018 by Nelson Education Limited 35

36 Mechanism: Reactions of epoxides: Copyright 2018 by Nelson Education Limited 36

37 8.7.2 Hydroboration: An anti-markovnikov addition Mechanism: Copyright 2018 by Nelson Education Limited 37

38 Regioselectivity: Stoichiometry: A single borane reagent reacts three times Copyright 2018 by Nelson Education Limited 38

39 Further transformation after hydroboration: Stereochemistry in hydroboration reactions Copyright 2018 by Nelson Education Limited 39

40 8.7.4 Hydrogenation of double bonds Metal catalyst serves as reaction surface: Copyright 2018 by Nelson Education Limited 40

41 8.7.5 Diene reactions Dienes: Electron delocalization: Copyright 2018 by Nelson Education Limited 41

42 8.7.6 Markovnikov addition of electrophiles to dienes Addition to isolated dienes Copyright 2018 by Nelson Education Limited 42

43 Addition to conjugated dienes Copyright 2018 by Nelson Education Limited 43

44 thermodynamic product Copyright 2018 by Nelson Education Limited 44

45 8.7.7 Alkyne reactions Structure of alkyne triple bond: Copyright 2018 by Nelson Education Limited 45

46 8.7.8 Markovnikov addition of electrophiles to alkynes Copyright 2018 by Nelson Education Limited 46

47 Stereoselectivity: Regioselectivity: Copyright 2018 by Nelson Education Limited 47

48 Addition of water: Acid-catalyzed hydration Step 1: Step 2: enol Copyright 2018 by Nelson Education Limited 48

49 Addition of water: Oxymercurartion-demercuration Note enol-ketone tautomerization in the final two steps. Copyright 2018 by Nelson Education Limited 49

50 8.7.9 Anti-Markovnikov additions to alkynes Copyright 2018 by Nelson Education Limited 50

51 Hydrogenation of alkynes Complete hydrogenation: Partial hydrogenation: Copyright 2018 by Nelson Education Limited 51

52 8.8 Patterns in Alkene Addition Reactions Copyright 2018 by Nelson Education Limited 52

53 Mechanistic patterns: Cyclic intermediates Copyright 2018 by Nelson Education Limited 53

54 Mechanistic patterns: Alkenes vs alkynes Copyright 2018 by Nelson Education Limited 54

55 Chapter summary Electron-rich p bonds can serve as nucleophiles in addition reactions with a variety of electrophiles. Regiochemistry of Markovnikov additions is controlled by carbocation stability. Many electrophilic addition reactions involve cyclic intermediates. Anti-Markovnikov addition can be achieved through hydroboration. Alkenes and alkynes react via similar mechanisms. Copyright 2018 by Nelson Education Limited 55

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