Summary_for_final_exam - Chemistry 2262, section 1 Fall...

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Chemistry 2262, section 1 Fall 2010 SUMMARY OF MAJOR THINGS TO KNOW FOR THE FINAL EXAM 1 - EXTENDED SUMMARY ( NOTE: You will need to know the mechanism for items with an “*”) 1.1. Spectroscopy IR: recognize characteristic bands for OH, NH, C=O, C-O, C=C, C C, aromatic. 1 H NMR: equivalence of functional groups, splitting pattern (N+1 rule), chemical shifts depending on substitution (number and electronegativity of substituents). Recognize characteristic features of isolated methyl, ethyl, isopropyl, tert -butyl groups, aromatic (various substitutions), vinyl. 1.2. Aromaticity = Special Stability from Circular Resonance. Criteria for aromaticity. 1.3. Draw Molecular Orbitals using the Polygon Method to determine aromaticity. 1.4. Classify compounds as aromatic, antiaromatic, and non-aromatic 1.5. Draw resonance structures of aromatic compounds The more resonance structures you can draw, the more stable the molecule is 1.6. Heterocyclic aromatic systems Only one pair of electrons of a heteroatom are considered, the rest ignored Everything else is the same 1.7. Nomenclature of Mono, Di and Trisubstituted Aromatic Compounds Ortho ( o ), Meta ( m ), Para ( p ) Numerical Order then Alphabetical Order *1.8. Electrophilic Aromatic Substitution (EAS); Reactions for Mono-substitution 1.9. Side chain reactions (radical benzylic bromination, further transformation of benzyl bromides (nucleophilic substitution, elimination), permanganate oxidation. *1.10. Diazotization of Aminobenzene. Nitrosation of secondary amines (Chapter 15.11) 1.11. Sandmeyer and related transformations of aryldiazonium salts (Chapter 15.9) Transformation of diazonium to F (Schiemann), Cl, Br, I, CN. Hydrolysis and reaction with H 3 PO 2 . 1.12. Regioselectivity in EAS for di- and tri-substitution, substituent effects. Resonance vs. Inductance (Resonance prevails, only matters for halogens: F, Cl, Br, I) The most activating substituent determines the site of the attack 1.13. Activating and Deactivating effects; Relative order of reactivity of substituted benzene compounds for EAS. 1.14. Synthetic strategies using EAS Order of adding substituents is important Anilines do not react in Friedel-Crafts reaction, phenols do react (although slowly, mono- substitution prevails). Using sulfonation-desulfonation and diazotization to introduce substituents into desired positions (see Problem 19, p. 699, and example on p. 702). Strongly activating substituents may result in multiple substitution Friedel-Crafts reaction do not occur with deactivated aromatic substrates (should be at least as active as Ar-Hal). 1.14. Effect of substituents on p K a . *1.15. Nucleophilic Aromatic Substitution (NAS). 1.16.
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This note was uploaded on 09/25/2011 for the course CHEM 2262 taught by Professor Smith during the Spring '08 term at LSU.

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Summary_for_final_exam - Chemistry 2262, section 1 Fall...

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