Chapter 8. Aromaticity
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1 Chapter 8. Aromaticity Learning objectives: 1. Name benzene derivatives. 2. Recognize aromatic compounds. 3. Explain the trend for the acidity of substituted phenol using the concept of electrondonating and electron-withdrawing groups, and inductive and resonance effects. 4. Write the oxidation of the benzylic groups with C-H bond(s) to benzoic acid. 5. Write the electron-pushing (arrow-pushing) mechanisms for the electrophilic aromatic substitution of benzene including halogenation, nitration, sulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation. 6. Explain the trend for the reactivity of substituted benzene toward electrophilic aromatic substitution using the concept of electron-donating and electron-withdrawing groups. 7. Recognize the reagents for reduction of nitro group to amino group. Sections to be covered 8.1 Introduction of Aromatic Compounds 8.2 Nomenclature of Monosubstituted Benzenes 8.3 Electrophilic Aromatic Substitution 8.4 Chemical Transformation of Some Substituents of Benzene 8.5 Nomenclature of Disubstituted and Polysubstituted Benzene 8.6 Reactivity of Substituted Benzene 8.7 The Effect Substituent on pka 8.1 Introduction of Aromatic Compounds A. Aromatic compounds are unusually stable The resonance of benzene provides additional stabilization. H 2 Ni H = kcal/mol 1
2 + 3H 2 cyclohexatriene (hypothetical) 36 kcal/mol Energy + H 2 + 3H kcal/mol kcal/mol (-28.6x3) kcal/mol B. The Criteria of Being Aromatic (i) Cyclic molecule (ii) Every atom has p orbital (iii) Planar molecule (iv) Number of delocalizable electrons complies with 4n+2 rule (as compared with 4n rule) Integral numbers that comply with the 4n+2 equation: 2, 6, 10, 14, 18, 22, 26 4n+2 2
3 C. Examples 3
4 D. Heterocyclic Compounds Know the type of lone-pair electrons that are delocalizable. H N H N O S N 4
5 D. Self-assessment Questions Can you describe the criteria for aromaticity? Can you use the criteria for aromaticity to identify aromatic and non-aromatic compounds? Can you use orbital hybridization to identify whether the electron pair can contribute and form the aromatic compound? 8.2 Nomenclature of Monosubstituted Benzenes Know the name for all of the monosubstituted benzenes. Cl Br NO 2 CH 3 OH NH 2 SO 3 H OCH 3 CHO CO 2 H CH 3 CHCH 3 5
6 Know the name for all of Benzene-based Substituents. As substituent: A. Self-assessment Questions Can you name all the monosubstituted benzenes (12) and benzene-based substituents (3) listed in this section? 8.3 Electrophilic Aromatic Substitution Know why it s called electrophilic aromatic substitution. A. General reaction equation E + E + + H + 6
7 B. General mechanism C. Comparing Electrophilic Aromatic Substitution and Addition Reaction 7
8 D. Reaction coordinate diagram E. Halogenation of Benzene Cl 2 (Br 2 ) FeCl 3 (FeBr 3 ) Cl (Br) (i) How to derive the mechanism for halogenation of benzene? Retrosynthetic analysis 8
9 (ii) The role(s) of FeCl3 or FeBr3? (iii) Mechanism of halogenation F. Nitration of Benzene HNO 3 H 2 SO 4 NO 2 (i) What is the electrophile needed and how to get it? 9
10 (ii) What is the role of H2SO4? (iii) Mechanism of nitration G. Sulfonation of Benzene SO 3 H 2 SO 4 SO 3 H fuming H 2 SO 4 (i) What is the electrophile needed and how to get it? 10
11 (ii) Mechanism H. Friedel-Crafts acylation and alkylation of benzene RX AlCl 3 R RCOX AlCl 3 O C R 11
12 (i) What are the electrophiles? (ii) Example of Friedel-Crafts alkylation 12
13 (iii) Example of Friedel-Crafts acylation I. Self-assessment Questions Can you explain what is electrophilic aromatic substitution? Can you derive the general mechanism of electrophilic aromatic substitution and identify the rate-determining step Can you write the electron-pushing mechanisms for the electrophilic aromatic substitution of benzene including halogenation, nitration, sulfonation, Friedel- Crafts alkylation, and Friedel-Crafts acylation. Can you identify the reagents and acid catalysts needed for various electrophilic aromatic substitutions, and complete these reactions? Can you explain the difference between electrophilic aromatic substitution and addition reaction? 13
14 8.4 Chemical Transformation of Some Substituents of Benzene A. Reduction O H 2, Pd/C NO 2 H 2, Pd/C 14
15 B. Oxidation 15
16 C. Self-assessment Questions Can you recognize all the reagents used for reduction and oxidation in this section? Can you complete the reduction and oxidation with similar functional groups attached to benzene as shown in this section and provide the corresponding products? Can you combine all the reactions you have learned so far and complete a multi-step synthesis? 8.5 Nomenclature of Disubstituted and Polysubstituted Benzene A. Disubstituted Benzenes 16
17 17
18 B. Trisubstituted Benzene C. Polysubstituted Benzene 18
19 D. Self-assessment Questions Can you name all the disubstituted benzenes using ortho (O), meta (m) and para (p), or numbering systems? 8.7 Reactivity of Substituted Benzene Know what are Electron-donating group (EDG) and electron-withdrawing group (EWG) Know how to judge EDG and EWG can predict the possible outcomes from a reaction. A. The Influence of EDG and EWG on the Electron Density of Substituted Benzene Know how to use resonance effect and inductive effect B. Strong Electron-donating Group 19
20 C. Moderate Electron-donating Group D. Weak Electron-donating Group 20
21 E. Moderate Electron-Withdrawing Group F. Strong Electron-Withdrawing Group 21
22 G. Influence of EDG and EDW on the Reaction Rate of Benzene (i) What is the correct order of decreasing reactivity (fastest to slowest) toward the electrophilic aromatic substitution for the following compounds? Cl CH 3 OCH 3 NO 2 I II III IV V Resonance effect > inductive effect (mostly) 22
23 H. Self-assessment Questions Can you describe what are resonance effect and inductive effect? Can you recognize EDG and EWG using resonance and inductive effects? Can you explain the trend for the reactivity of substituted benzene toward electrophilic aromatic substitution using the concept of electron-donating and electron-withdrawing groups? 8.7 The Effect of Substituents on pka Know the influence of EDG and EWG on the electron density of substituted benzene. Know the influence of EDG and EWG on the stability of conjugate bases. A. What Influence that EDG and EWG Will Have on Acidity? 23
24 B. Substituted Phenols OH OH OH OH OH OH O H 3 CO H 3 C Cl O I II III IV V 2 N H VI pka C. Substituted Benzoic Acids CO 2 H CO 2 H CO 2 H CO 2 H CO 2 H CO 2 H O H 3 CO H 3 C Br O I II III IV V 2 N CH VI 3 pka
25 D. Substituted Prononated Anilines NH 3 NH 3 NH 3 NH 3 NH 3 NH 3 O H 3 CO H 3 C Br O I II III IV V 2 N H VI pka Which of the following amine is most basic? E. Self-assessment Questions Can you describe the influence of EDG and EWG on the electron density of substituted benzenes? Can you describe the influence of EDG and EWG on the stability of the conjugate bases for the substituted benzenes? Can you explain the trend of acidity for the substituted benzenes using the concept of electron-donating and electron-withdrawing groups? 25
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