Freshman Organic Chemistry II (CHEM 125B)
Green chemistry needs new asymmetric reactions and safer, more environmental Mitsunobu reactions. The Mitsunobu mechanism is general and reliable, but atom inefficient, generating almost 30 times as much weight of by-products as of the water it is designed to eliminate. Admirably green processes include autoxidation of aldehydes to carboxylic acids using only O2, and oxidation of alcohols by loss of H2 using a ruthenium catalyst. Relative pKa values of carboxylic acids provide insight into the role of inductive and resonance effects in organic transformations. One analysis suggests that the special acidity of carboxylic acids owes four times as much to inductive as to resonance effects. Carboxylic acids can be prepared both by oxidation and by reduction.
00:00 - Chapter 1. Mitsunobu Inversion and Atom Efficiency
05:38 - Chapter 2. Green Oxidation of Aldehydes and Alcohols
18:49 - Chapter 3. Understanding the Acidity of Carboxylic Acids
29:26 - Chapter 4. Preparing Carboxylic Acids by Oxidation and Reduction
Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu
This course was recorded in Spring 2011.
Tagged under: green chemistry,asymmetric reactions,Mitsunobu reaction,atom efficiency,active methylene,DEAD,autoxidation,Milstein catalysis,pKa,inductive effect,resonance stabilization
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