2016 Pearson Education, Inc. Isolated and Conjugated Dienes

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1 2016 Pearson Education, Inc. Isolated and Conjugated Dienes

2 2016 Pearson Education, Inc. Reactions of Isolated Dienes

3 2016 Pearson Education, Inc. The Mechanism

4 Double Bonds can have Different Reactivities 2016 Pearson Education, Inc.

5 2016 Pearson Education, Inc. Reactions of Conjugated Dienes

6 2016 Pearson Education, Inc. 1,2-Addition and 1,4-Addition

7 Mechanism for the Reaction of a Conjugated Diene 2016 Pearson Education, Inc.

8 The Diels Alder Reaction forms a Six-Membered Ring 2016 Pearson Education, Inc.

9 2016 Pearson Education, Inc. The Mechanism

10 Faster if there is an Electron Withdrawing Group on the Dienophile 2016 Pearson Education, Inc.

11 The Electron Withdrawing Group makes the Electrophile a better Electrophile 2016 Pearson Education, Inc.

12 2016 Pearson Education, Inc. Another Diels Alder Reaction

13 Alkynes can also be Dienophiles The cyclic product has two double bonds Pearson Education, Inc.

14 The Stereochemistry of the Diels Alder Reaction The product will be a racemic mixture Pearson Education, Inc.

15 How to Determine the Reactants of a Diels Alder Reaction 2016 Pearson Education, Inc.

16 Benzene is an Aromatic Compound The delocalization energy of benzene is 36 kcal/mol Pearson Education, Inc.

17 Criteria for a Compound to be Aromatic It must have an uninterrupted cloud of π electrons.(cyclic, planar, every ring atom must have a p orbital). The π cloud must have an odd number of pairs of π electrons Pearson Education, Inc.

18 Criteria for Aromaticity Uninterrupted arrangement of p cloud Cyclic molecule Every atom in the ring must have a p orbital Molecule has to be planar Total number of p-electron pairs is odd (1,3,5 ) Exceptionally stable molecules 2016 Pearson Education, Inc.

19 Examples of Compounds that are not Aromatic Cyclobutadiene has an even number of pairs of π electrons. Cyclooctatetraene has an even number of pairs of π electrons and it is not planar Pearson Education, Inc.

20 Nonaromatic and Aromatic Compounds 2 pairs of p electrons 2 pairs of p electrons 3 pairs of p electrons planar nonplanar planar 2016 Pearson Education, Inc.

21 Resonance Contributors and the Resonance Hybrid 2016 Pearson Education, Inc.

22 Cyclopentadienyl anion Resonance contributors. Overall every C atom has the same amount of negative charge 2016 Pearson Education, Inc. charge equally distributed

23 Benzene Benzene: planar, ring, all atoms have p orbitals, 3 pairs of p electrons Pearson Education, Inc.

24 2016 Pearson Education, Inc. Aromatic Compounds

25 Aromatic Heterocyclic Compounds A ring atom that is not carbon is called a heteroatom Pearson Education, Inc.

26 Pyridine N The lone pair is not part of the aromatic ring system. Electrons are located in sp 2 -hybrid orbital. N 2016 Pearson Education, Inc.

27 Pyrrole N H N H Lone pair is part of p-system, N is sp 2 hybridized 2016 Pearson Education, Inc.

28 Resonance contributors Pyrrole N H N H N H N H N H 2016 Pearson Education, Inc. pos. charge

29 Furan O O Second lone pair is located in sp 2 -hybridized Orbital Pearson Education, Inc.

30 Furan Resonance contributors O O O O O 2016 Pearson Education, Inc.

31 Bicyclic Heterocyclic Aromatics N N N N H N N H quinoline indole purine 2016 Pearson Education, Inc.

32 Nomenclature of Monosubstituted Benzenes State the name of substituent and add the word benzene 2016 Pearson Education, Inc.

33 Nomenclature Many trivial names in use 2016 Pearson Education, Inc.

34 2016 Pearson Education, Inc. Nomenclature

35 How Benzene Reacts Aromatic compounds such as benzene undergo electrophilic aromatic substitution reactions Pearson Education, Inc.

36 Benzene Reacts with Electrophiles The π electrons above and below the ring make benzene a nucleophile. Benzene attacking an electrophile is like an alkene attacking an electrophile Pearson Education, Inc.

37 Benzene undergoes Substitution, not Addition Aromaticity is restored in the product from electrophilic substitution Pearson Education, Inc.

38 Benzene undergoes Substitution, not Addition The reaction of benzene with an electrophile forms the aromatic substitution product, not the nonaromatic addition product Pearson Education, Inc.

39 An Electrophilic Aromatic Substitution Reaction An electrophile (Y + ) substitutes for H Pearson Education, Inc.

40 The Mechanism for Electrophilic Aromatic Substitution 2016 Pearson Education, Inc.

41 Generating the Electrophile: Halogenation Donating a lone pair to a Lewis acid weakens the Br Br or Cl Cl bond Pearson Education, Inc.

42 Halogenation of Benzene

43 Halogenation: Halogenation of Benzene 1 st step is generating an electrophile: FeBr 3 is a Lewis acid that coordinates with Br 2 and polarizes it, generating an electrophilic Br +

44 Halogenation of Benzene

45 Generating the Electrophile: Nitration 2016 Pearson Education, Inc.

46 Nitration: Nitration of Benzene

47 Nitration: Nitration of Benzene

48 Generating the Electrophile: Sulfonation 2016 Pearson Education, Inc.

49 Sulfonation of Benzene

50 Sulfonation of Benzene

51 Generating the Electrophile: Friedel Crafts Acylation and Alkylation 2016 Pearson Education, Inc.

52 Friedel-Crafts Acylation of Benzene

53 Friedel-Crafts Acylation of Benzene

54 Friedel-Crafts Alkylation of Benzene

55 Friedel-Crafts Alkylation of Benzene

56 How Some Substituents on a Benzene Ring Can be Chemically Changed

57 How Some Substituents on a Benzene Ring Can be Chemically Changed

58 Nomenclature of Disubstituted Benzenes

59

60 The Effect of Substituents on Reactivity Monosubstituted benzenes undergo electrophilic aromatic substitution. Substituents influence reactivity. Substituents determine position of second electrophilic substitution. Substituents that increase electron density increase reactivity. Substituents that decrease electron density decrease reactivity.

61 The Effect of Substituents on Reactivity

62 Donating and Withdrawing Electrons by Resonance

63 Electron-donating Substituents O CH 3 H 3 C H 3 C O O O CH 3 O CH 3 Resonance contributors increase electron density in ortho and para positions. Overall electron density is bigger.

64 Donating and Withdrawing Electrons by Resonance

65 Electron-withdrawing Substituents O N O O N O O N O O N O O N O Resonance contributors decrease electron density in ortho and para positions. Overall electron density is lower.

66 Substituent Effects D W O CH 3 O N O Both types of substituents, electron Donating and electron Withdrawing, act on the same positions, namely ortho and para, however, in opposite directions.

67 Relative Reactivity of Substituted Activating Benzenes Deactivating

68

69 Classification of Substituents Activating Substituents (ortho/para directing): NH 2 prim. Amines NHR sec. Amines tertiary amines NR 2 phenolic OH OH phenol ethers OR NH CR' amides phenolic esters R alkyl substituents halides X O O O CR' Strongly activating weakly activating deactivating

70 Classification of Substituents Deactivating Substituents (meta directing): + O CH aldehydes O + COR O esters + COH carboxylic acid weakly deactivating + C N nitrile + SO 3 H sulfonic acid O N O nitro strongly deactivating NR 3 ammonium

71 The Effect of Substituents on Orientation 1. All activating substituents direct an incoming electrophile to the ortho and para positions.

72 The Effect of Substituents on Orientation 2. The weakly deactivating halogens also direct an incoming electrophile to the ortho and para positions.

73 The Effect of Substituents on Orientation 3. All moderately deactiating and strongly deactivating substituents direct an incoming electrophile to the meta position.

74

75

76 Organizing what we know about the Reactions of Organic Compounds 2016 Pearson Education, Inc.

Key ideas: In EAS, pi bond is Nu and undergoes addition.

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