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Freshman Organic Chemistry I

Yale,, Spring 2011 , Prof. Michael McBride

Updated On 02 Feb, 19

Overview

Mechanism: How Energies and Kinetic Order Influence Reaction Rates - Peculiar Rate Laws, Bond Dissociation Energies, and Relative Reactivities - Rate and Selectivity in Radical-Chain Reactions - Electronegativity, Bond Strength, Electrostatics, and Non-Bonded Interactions - Solvation, H-Bonding, and Ionophores - Brnsted Acidity and the Generality of Nucleophilic Substitution - Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate, Nucleophile - Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon - Pentavalent Carbon? E2, SN1, E1 - Cation Intermediates. Alkenes: Formation, Addition, and Stability - Carbocations and the Mechanism of Electrophilic Addition to Alkenes and Alkynes - Nucleophilic Participation During Electrophilic Addition to Alkenes - Addition to Form Three-Membered Rings: Carbenoids and Epoxidation.

Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis - Metals and Catalysis in Alkene Oxidation, Hydrogenation, Metathesis, and Polymerization - Isoprenoids, Rubber, and Tuning Polymer Properties - Alkynes. Conjugation in Allylic Intermediates and Dienes - Linear and Cyclic Conjugation Theory. 4n+2 Aromaticity - Aromatic Transition States: Cycloaddition and Electrocyclic Reactions - Electronic and Vibrational Spectroscopy - Functional Groups and Fingerprints in IR Spectroscopy. Precession of Magnetic Nuclei - Medical MRI and Chemical NMR - Diamagnetic Anisotropy and Spin-Spin Splitting - Higher-Order Effects, Dynamics, and the NMR Time Scale.

C-13 and 2D NMR. Electrophilic Aromatic Substitution - Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg - Triphenylmethyl and an Introduction to Carbonyl Chemistry - Mechanism and Equilibrium of Carbonyl Reactions - Imines and Enamines. Oxidation and Reduction - Oxidation States and Mechanisms - Periodate Cleavage, Retrosynthesis, and Green Chemistry - Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison - Green Chemistry. Acids and Acid Derivatives - Acids and Acid Derivatives - Acyl Insertions and [gr]α-Reactivity - [gr]α-Reactivity and Condensation Reactions - Proving the Configuration of Glucose and Synthesizing Two Unnatural Products - Review: Synthesis of Cortisone.

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Lecture 27: Triphenylmethyl and an Introduction to Carbonyl Chemistry

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Lecture Details

Freshman Organic Chemistry II (CHEM 125B)Painstaking studies of his "hexaphenylethane" and its reactivity convinced Gomberg that he had prepared the first trivalent carbon compound, triphenylmethyl radical, the discovery of which marked the emergence of fundamental organic chemistry in America. Isotopic labeling could decide whether protonated cyclopropane plays a role in Friedel-Crafts alkylation. C-13 NMR spectra of aldehydes and ketones show how characteristic chemical shifts are established empirically. The carbonyl group is thermodynamically stable but kinetically reactive. Its acid- and base-catalyzed reactions often involve loss of an [gr]α-proton to form an enol or enolate intermediate. Carboxylic acids display four fundamentally different reaction patterns. Acid-catalyzed hydrolysis of acetals illustrates a multistep reaction mechanism involving the carbonyl group.0000 - Chapter 1. Triphenylmethyl Chemistry Comes to America 1539 - Chapter 2. Protonated Cyclopropane in Friedel-Crafts Alkylation?2205 - Chapter 3. Carbonyl Compounds Energy and Spectroscopy 2606 - Chapter 4. Carbonyl Compounds Reactivity Patterns Complete course materials are available at the Open Yale Courses website httpoyc.yale.eduThis course was recorded in Spring 2011.