Chem 263 - Lecture Outline & Assignment #2
Readings
Problems
Outline
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Readings:
TWG Solomons and CB Fryhle "Organic Chemistry" 8th Edition (2004):
- Functional Group List on pp 70-71 and (Periodic Table) one page back from Inside Back Cover
- Relative Strength of Acids and Bases on Inside Front Cover - same table page 105
- Chapter 14 – Aromatic Compounds read for overview
- study sections 14.1 to 14.10
- Chapter 15 – Reactions of Aromatic Compounds
- Chapter 20 – Sections 20.1; 20.6; 20.7; 20.8; 20.11
- Chapter 21 – Phenols and Aryl Halides
Problems:
Do Not turn in, answers available in "Study Guide and Solutions Manual for Organic Chemistry" by Solomons and Fryhle.
Chapter 14:
14.2;14.10; 14.12; 14.16
Chapter 15:
15.1; 15.3; 15.4; 15.7; 15.9; 15.10; 15.13; 15.19; 15.20; 15.26
Chapter 20:
20.11; 20.12; 20.15; 20.16
Chapter 21:
21.1; 21.2; 21.3; 21.13
Lecture Outline 2: Aromaticity and Reactions of Benzene Derivatives (Electrophilic Aromatic Substitution)
- Review of Aromaticity, Benzene, and Nomenclature
- Structure and Properties of Benzene
- Resonance Stabilization
- Substitution vs. Addition Reactions
- Annulenes and Huckel's Rule
- Coplanar Systems of (4n+2) pi Electrons
- Aromatic Ions - Acidity of Parent Compounds
- Other Aromatic Systems - Naphthalene, Anthracene, and Heteroaromatic Systems
- Five membered rings - Furan, Pyrrole, Thiophene, Imidazole
- Six membered rings - Pyridine, Pyrimidine
- Nomenclature of Monosubstituted Benzenes
- As Derivatives of Benzene
- Common names (Phenol, Aniline, Anisole, etc.)
- Nomenclature of Multiply-Substituted Benzenes
- Using Numbers and Common Names
- Ortho, Meta, Para Nomenclature
- Electrophilic Substitution Reactions
- Benzene - General Mechanism
- Halogenation - X2
- Nitration - HNO3
- Sulfonation - SO3 .H2SO4
- Friedel-Crafts Alkylations - Lewis Acid + RX
- Friedel-Crafts Acylations - Acylium Ions from Acid Halides / Anhydrides
- Use of Clemmensen Reduction (Zn/Hg and HCl) with Friedel-Crafts Acylation
- Effects of Substituents
- Activation vs. Deactivation - Electron Donating vs Electron Withdrawing Groups
- Orientation - (Ortho-Para vs. Meta)
- Inductive vs. Resonance Effects
- Disubstituted Benzene Reactions
- Reactions of Side Chains and Substituents of Aromatic Systems
- Nitro to Amino to Diazonium Salts
- Reduction of Nitrobenzenes to Anilines and Diazotization (NaNO3 and HCl)
- Replacement of Diazo Group
- Azo Coupling and Dyes
- Oxidation of Alkyl Side Chains of Aromatic Compounds to Carboxylic Acids
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