Reaction Coordinate Diagrams for the Two Benzene Reactions
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1 Organic Chemistry 8 th Edition Paula Yurkanis Bruice Aromatic compounds such as benzene undergo electrophilic aromatic substitution reactions: Chapter 18 Reactions of Benzene and Substituted Benzenes Cap. 18 ( ) 1 2 Benzene is a nucleophile that reacts with an electrophile An electrophilic substitution yields an aromatic product, which is significantly more stable than the addition reaction Reaction Coordinate Diagrams for the Two Benzene Reactions 3 4 There are five common electrophilic aromatic substitution reactions: General Mechanism for Electrophilic Aromatic Substitution of Benzene 1. Halogenation by 2. Nitration 3. Sulfonation 4. Friedel Crafts acylation 5. Friedel Crafts alkylation 5 6
2 Halogenation of Benzene Lewis acid weakens the Br Br (or Cl Cl) bond, which makes the halogen a better electrophile: 7 8 Mechanism for bromination: B: Bromide or Benzene The catalyst is regenerated: 9 10 Nitration of Benzene Nitronium ion formation: Electrophilic aromatic substitution: 11 12
3 Sulfonation of Benzene Sulfonic acid is a strong acid: Sulfonation is reversible: Reaction coordinate diagram for electrophilic aromatic substitution: Friedel Crafts Alkylation of Benzene Mechanism for Friedel Crafts alkylation: 17 18
4 The carbocation will rearrange to a more stable species: However, 100% of the 2-methyl-2-phenylbutane product can be obtained if a bulky alkyl halide is used: Friedel Crafts Acylation Reactions Mechanism for Friedel Crafts acylation: The electrophile is an acylium ion: Must be carried out with more than one equivalent of AlCl 3 : Friedel Crafts alkylation will not produce a good yield of an alkylbenzene containing a straight-chain group, because the carbocation will rearrange: Acylium ions, however, do not rearrange: 23 24
5 Methodologies Used for the Reduction Step Summary: Electrophilic Aromatic Substitution Summary of Friedel Crafts Reactions Examples of Substituted Benzenes Substituted benzenes undergo the five electrophilic aromatic substitution reactions discussed so far The slow step of an electrophilic aromatic substitution reaction is the formation of the carbocation intermediate: Electron-donating substituents increase the rate of substitution reactions by stabilizing the carbocation intermediate. Electron-withdrawing substituents decrease the rate of substitution reactions by destabilizing the carbocation intermediate
6 Inductive Electron Withdrawal Resonance Electron Donation and Withdrawal Substituents such as NH 2, OH, OR, and Cl donate electrons by resonance, but they also withdraw electrons inductively: Electron Donation by Hyperconjugation Substituents such as C=O, CΞN, SO 3 H, and NO 2 withdraw electrons by resonance: Electron-donating substituents increase the reactivity of the benzene ring toward electrophilic aromatic substitution Electron-withdrawing substituents decrease the reactivity of the benzene ring toward electrophilic aromatic substitution Electron-Donating Substituents Electron donation into the benzene ring by resonance is more significant than inductive electron withdrawal from the ring: 35 36
7 These substituents are less effective in donating electrons into the ring because Resonance donation into the benzene ring competes with resonance donation into the carbonyl Inductive withdrawal into the benzene ring also occurs Overall, these substituents weakly release electrons Alkyl, aryl, and CH=CHR groups are weakly activating substituents because they are slightly more electron donating than they are electron withdrawing: These substituents donate into the ring by resonance and withdraw electrons from the ring inductively: 39 They withdraw electrons inductively more strongly than they donate electrons by resonance 40 These substituents withdraw electrons both inductively and by resonance: These substituents are powerful electron-withdrawing groups: Except for the ammonium ions, these substituents withdraw electrons both inductively and by resonance 41 42
8 The substituent already attached to the benzene ring determines the location of the new substituent: All activating substituents are ortho para directors: The weakly deactivating halogens are ortho para directors: All substituents that are more deactivating than halogens are meta directors: An ortho,para-directing substituent: An ortho,para-directing substituent: 47 48
9 An meta-directing substituent: The ortho para product ratio decreases with an increase in the size of the substituents: Product Ratio: Regioselectivity Methoxy and hydroxy substituents are so strongly activating that halogenation is carried out without a Lewis acid: The presence of Lewis acid and excess bromine generates the tribromo derivative: A benzene ring with a meta director cannot undergo a Friedel Crafts reaction: Aniline and N-substituted anilines do not undergo Friedel Crafts reaction: 53 Phenol and anisole undergo Friedel Crafts reactions at the ortho and para positions Aniline cannot be nitrated, because it is oxidized by nitric acid 54
10 In designing a disubstituted benzene, consider the order of substitution: The Friedel Crafts acylation must be carried out first, because the nitro group is strongly deactivating: In the synthesis of para-chlorobenzoic acid from toluene, the methyl group is oxidized after chlorination: To synthesize p-propylbenzenesulfonic acid: Introduce the propyl group by Friedel Crafts acylation followed by reduction. Sulfonation of the propylbenzene product affords the para derivative. In the synthesis of meta-chlorobenzoic acid, the methyl group is oxidized before chlorination: 57 How is the meta derivative prepared? Friedel Crafts acylation Sulfonation Carbonyl reduction 58 Synthesis of Trisubstituted Benzenes 59 Steric hindrance makes the position between the substituents less accessible 60
11 If the two substituents have similar activating properties, neither will dominate: A strongly activating substituent will win out over a weakly activating substituent or a deactivating substituent 61 62
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