Lecture 19 and 20 In Class Summary
Lecture 19 and 20 In Class Summary CHEM 225
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This 1 page Class Notes was uploaded by MelLem on Tuesday April 19, 2016. The Class Notes belongs to CHEM 225 at Simmons College taught by Professor gurney in Spring 2016. Since its upload, it has received 18 views. For similar materials see Organic chemistry 2 in Chemistry at Simmons College.
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Date Created: 04/19/16
CHEM 225 Organic Chemistry II Lecture 19 & Lecture 20 In Class Summary Lecture 19 – Enols and Enolates • Enolates and enols can form c-‐c bonds • The carbonyl species act as both the electrophil and nucleophile. o They must have alpha protons available. • Enol – Neutral at equilibrium with its keto tautomer • Enolate – negative charge, loses the proton o Keto + Strong base = enolate • When you have a choice of alpha protons, you can have a kinetic or a thermodynamic enolate o Kinetic Enolate – occurs on the less substituted side, less stable and easiest to grab. o Thermodynamic Enolate – Most stable, occurs on the more substituted side, given time to equilibrate Lecture 20 – Aldol Reactions & Claisen Reactions • Aldol o Has a beta hydroxyl o The starting materials are and aldehyde with an alpha proton o Gives you an aldehyde-‐alcohol product • Mixed Aldols o Gives a variety of products. o Also called crossed aldols o Has 2 different starting materials • Claisen Reactions o Starts with an ester o Carbonyl is the E+ and the Nu-‐ is the alpha proton o Similar to the acyl substitution Aldol and Claisen • Important in synthetic chemistry because they’re c-‐c bond forming reactions
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