Chapter 11

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Chapter 11 Oxidation in Organic terms Oxidation Addition of O, X2; loss of H2 Reduction Addition of H2; loss of O or X2 Neither Anytime you oxidize one carbon but reduce another (ex. Adding H and OH to adjacent carbons) Oxidation of alcohols Chromic Acid KMnO4 PCC Swern 1 ROH RCOOH RCOOH RCHO RCHO 2 ROH Ketone Ketone Ketone Ketone 3 ROH NR NR NR NR Why don t you oxidize 3 alcohols? [O]5 bonds to carbon=crazy talk!OHO[O]5 bonds to carbon=crazy talk!OHO You won t need to draw the structure of PCC, but you do need to recognize it. pyridinium chlorochromate (PCC)CrOOClO N+Hpyridinium chlorochromate (PCC)CrOOClO N+H You don t need to know all the reagents of Swern Oxidation for Mr. Baker s class. Tollens Test Not tested in this course. o Qualitative test for aldehydes o Aldehyde + AgNO3 Carboxylic acid + silver metal o If you see the silver metal coating the tube, then you know you have an aldehyde.

Chapter 11 • Oxidation in ... PCC Swern 1° ROH RCOOH RCOOH RCHO RCHO ... o If you see the silver metal coating the tube, then you know you have an aldehyde.

  Chapter, Metal, Chapter 11