شیمی آلی پیشرفته کری انگلیسی

شیمی آلی پیشرفته کری انگلیسی

اسلاید 1: ADVANCED ORGANIC CHEMISTRY Dr. Alireza banaei

اسلاید 2: REFERENCES1. Advanced Organic Chemistry, Part A: “Structure and Mechanisms”Francis A. Carey & Richard J. Sundberg3rd Edition, Plenum Press, 1990.2. Advanced Organic Chemistry: Reactions, Mechanisms and Structure”Jerry March3rd Edition, John Wiley & Sons, 1985.

اسلاید 3: Table of Contents:Chapter 1: Chemical Approach to Chemical Bonding Chapter 9: Aromaticity Chapter 2: Stereochemical PrinciplesChapter 3: Conformational, Steric, and Stereo Electronic Effects Chapter 4: Study and Description of Organic Reaction Mechanisms Chapter 5: Nucleophilic SubstitutionChapter 6: Polar Addition and Elimination ReactionsChapter 7: Carbanions and Other Nucleophilic Carbon Species

اسلاید 4: Chapter 1 Chemical Approach to Chemical Bonding

اسلاید 5: IntroductionOrganic Chemistry Main Areas:a) Structure: Description of bonding in organic molecules and the methods for determining, analyzing, and predicting molecular structure.b) Dynamics: Study of physical properties and chemical transformations of molecules.c) Synthesis: Those activities which are directed toward finding methods which convert existing substances into different compounds.Advanced Organic Chemistry (Chapter 1) a. banaei

اسلاید 6: Advanced Organic Chemistry (Chapter 1) a. banaei1916: G. N. Lewis: sharing of electron pairs between atoms1927: mansoori & London: Quantum mechanics treatment of H2 molecule; Beginning of Valance Bond Theory (VBT)Central Feature of VBT: Exchange (resonance) of electrons between two nuclei.The Actual molecule is the hybrid of the “Canonical Forms”For example:1-1 Valance Bond Approach to Chemical Bonding

اسلاید 7: Advanced Organic Chemistry (Chapter 1) a. banaeiComplex Molecules Lead to Complex Wave FunctionsLinus Pauling’s Key Idea: 1) Hybridization Theory 2) Resonance TheoryHybrid orbitals are highly directed than s and p orbitals and hence: More effective Overlap Stronger bonds

اسلاید 8: Advanced Organic Chemistry (Chapter 1) a. banaeiThe p bond in ethyleneThe p bonds in acetylene

اسلاید 9: Advanced Organic Chemistry (Chapter 1) a. banaeiAngle Strain in three and four-membered ringsC-C bonds: decreased s character (17%) increased p character (83%)C-H bonds: increased s character (33%) decreased p character (67%)

اسلاید 10: Advanced Organic Chemistry (Chapter 1) a. banaeiPropellanesAngle Strain cause to increased in chemical reactivity involving CLEAVAGE of the central bond.

اسلاید 11: Advanced Organic Chemistry (Chapter 1) a. banaeiResonance Theory (Different Lewis Structure for a Molecule)Elements of Resonance Theory for Qualitative Application:1. The actual molecule is combination of ALL Lewis structures.2. Maximum number of valance electrons around each atom (e.g. 2 for H atom and 8 for first row elements)3. Stable structures that approximate the actual molecule have following features: a) maximum number of covalent bonds: b) minimum separation of unlike charges c) Placement of negative charge on the most electronegative atom or reverse

اسلاید 12: Advanced Organic Chemistry (Chapter 1) a. banaeiThe Use of Resonance Concept:1. Relative Acidity of Isobutene and Acetone:2. Stability of Allyl Cation:

اسلاید 13: Advanced Organic Chemistry (Chapter 1) a. banaei3. a,b-Unsaturated CompoundsStructural Features of a,b-Unsaturated Compounds:C=O band is weaker than in saturated compounds (typically at 1690 cm-1 vs. 1730 cm-1 for saturated compounds)b) b-carbon atom is less shielded (lower electron density) than for simple alkenes (13C-NMR)c) Increased reactivity of C=C vs. simple alkenes toward nuclephies.

اسلاید 14: Advanced Organic Chemistry (Chapter 1) a. banaeiConflictio