This preview shows page 1. Sign up to view the full content.
Unformatted text preview: Perkins, Chem 2303002 Fall 2009, Exam I Review Exam I Friday October 2, 2009; 12:20 1:10 pm You must have your student I.D. with you to take the exam. All exams should be written in blue or black nonerasable pen or no regrade will be considered. No notes, calculators or models permitted. Students AH: Anderson Hall 210 Students IZ: Willey Hall 125 Review Session/Q&A session Wednesday September 30 at 78pm in Smith 231. This exam will cover Chapters 14, 15, & 16. Chapter 14: Ethers, Epoxides, and Sulfides Nomenclature: Be able to draw or name simple ethers using either common (alkyl alkyl either) or IUPAC (alkoxy alkane) nomenclature. For epoxides be able to name or draw using either alkene oxide or oxirane. Also know structure of furan, tetrahydrofuran and 1,4 dioxane. Properties: Ethers Polarity, usage as polar solvents, reactivity, complexes with electrophiles; Crown Ethers structure and complexes with metal ions; Epoxides reactivity Spectroscopy: IR: more of what you don't see NO Carbonyl, NO alcohol; 1H NMR: 3.5 4ppm (protons on carbon adjacent to oxygen) Ether Synthesis and Reactions: Williamson Ether Synthesis (Sn2); Intramolecular Williamson Ether Synthesis to make epoxides or rings; Alkoxymercurationdemercuration (1. Hg(OAc)2, ROH; 2. NaBH4); Cleavage with Acids Epoxide Synthesis and Reactions: Alkene with Perbenzoic Acid; Intramolecular Cyclization; Acid and Base Ring opening; Organolithium and Grignard Reactions Sulfides: more reactive than ethers, common alkylating reagents in biological systems Chapter 15: Conjugated Systems: Characteristics: Difference between conjugated, isolated and cumulative double bonds; molecular orbital diagrams for overlapping pi systems Allylic Cation, Radical, and Anion Intermediates: Generation of intermediates; stability; resonance forms; MO Orbitals Addition Reactions to Conjugate Dienes: Resonance forms leading to 1,2 and 1,4 products; Kinetic vs Thermodynamic Control which product is favored under which conditions; Perkins, Chem 2303002 Fall 2009, Exam I Review DielsAlder Reaction: Pericyclic reactions concerted reaction (1 transition state); Diene electron rich, scis diene; Dienophiles electron poor; syn addition of dienophile substitutents; Stereochemistry from endo rule; 1,2 or 1,4 relationship of substitutents Construction of pi Molecular orbital (MO) diagrams: # of porbital = # of MO's required; determine whether each orbital is bonding, antibonding or nonbonding; Identify Highest occupied molecular orbital (HOMO) and Lowest unoccupied molecular orbitals (LUMO) involved in pericyclic reactions; Understand the Conservation of Orbital Symmetry Theory to be able to predict which pericyclic reactions will occur; Must be able to draw 2, 3, and 4p orbital system MO diagrams Chapter 16: Aromatic Compounds: Benzene: Stable compound that doesn't react like alkene; MO diagram Aromatic Systems: Cyclic molecules with continuous ring of porbitals, lowers the overall energy; Polygon rule; Huckel Rule (4N+2 electrons); Heterocyclic systems AntiAromatic Systems: Cyclic molecules with continuous ring of porbitals, but does not lower overall energy; Polygon rule; Huckel Rule (4N electrons) Nonaromatic: No continuous loop of porbitals usually due to planarity Nomenclature of Benzene Derivatives: Must know common names phenol, toluene, aniline, styrene, etc.; 1substitutent substitutent + benzene; 2substitutents 1,2 ortho, 1,3 meta, 1,4 para; Benzene as a substitutent phenyl (Ph) and Benzyl (CH2Ph) Spectral properties: NMR shifts 78 ppm; Understand effects of ortho, meta, or para substitution on splitting patterns; IR 3030cm1 (=CH), 1600cm1 (C=C) ...
View Full Document
This note was uploaded on 10/30/2011 for the course CHEM 2301 taught by Professor Gao during the Spring '07 term at Minnesota.
- Spring '07
- Organic chemistry