POD09Key - The mechanism for formation of this hydrazone...

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Problem of the Day #09 – Answer Key Deadline : IN CLASS on Tu 7/27/2010 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In lecture, we discussed the Wolff-Kishner reduction, which occurs when an aldehyde or ketone is heated with hydrazine (H2NNH2) in the presence of concentrated KOH. The overall transformation observed for the Wolff-Kishner reduction of acetophenone is shown below: Ph CH 3 O H 2 NNH 2 KOH, Ph CH 3 N NH 2 KOH, Ph CH 2 CH 3 + O H 2 hydrazone (not isolated) In lecture, we looked in detail at the mechanism for conversion of the hydrazone intermediate into the final Wolff-Kishner product.
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Unformatted text preview: The mechanism for formation of this hydrazone via reaction of hydrazine with the ketone starting material UNDER BASIC REACTION CONDITIONS is outlined below. Complete this mechanism by drawing curved arrows to show movement of electron pairs, and by drawing structures for each missing reaction intermediate. Ph C CH 3 O NH 2 NH 2 OH H OH OH OH Hydroxide departs as a leaving group - heating is required to overcome the activation barrier (a "strong" base is typically a "poor" leaving group) Ph C CH 3 N N H 2 H OH Ph C CH 3 O N NH 2 H H Ph C CH 3 O N NH 2 H Ph C CH 3 O N NH 2 H H...
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