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 34: Acids and Acid Derivatives

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Freshman Organic Chemistry II (CHEM 125B)Reactions of carboxylic acids and their salts include nucleophilic substitution and decarboxylation to leave enols, free radicals, or alkyl halides. A review of the IR spectroscopy of acid derivatives includes the use of vibrational coupling in the structure determination of anhydrides and imides. Many acid derivatives can be interconverted by substitution through a tetrahedral intermediate, and differences in acidity can be used to drive such reactions toward completion. Reduction of acid derivatives illustrates the challenge of designing selective reactions. Acidic and basic mechanisms allow conversion of nitriles to carboxylic acids. Ketenes provide routes to several acid derivatives. The Baeyer-Villiger oxidation of ketones to esters illustrates atom insertion into acyl-R bonds.0000 - Chapter 1. Reducing Carboxylic Acids to Carbonyl Groups0221 - Chapter 2. Decarboxylation Reactions1202 - Chapter 3. Acid Derivatives and their IR Spectra 1818 - Chapter 4. Interconversion of Acid Derivatives, Saponification2716 - Chapter 5. Selective Reduction of Acid Derivatives 4045 - Chapter 6. Nitriles and Ketenes4735 - Chapter 7. Insertion into the Acyl-R Bond Baeyer-Villiger OxidationComplete course materials are available at the Open Yale Courses website httpoyc.yale.eduThis course was recorded in Spring 2011.