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Unformatted text preview: 1 CHM 2123, Quiz #6: Oxidation and Reduction Assigned: October 26, 2006 Due: October 30, 2006 , before 5pm MARKING SCHEME 1. While preparing for the final exam, your TA tells one of your friends that the C=O bond-forming step in the mechanism of the oxidation with H 2 CrO 4 resembles an E2 elimination. Unfortunately, your friend did not understand the analogy. Explain this analogy with the help of mechanisms and a brief discussion (2 points) E 2 elimination has: Presence of a goodl leaving group (X = Br, OSO 2 R...) An antiperiplanar H on the ! carbon A base that attacks to form the C=C double bond H R 2 R 1 X H R 3 Base R 1 R 2 R 3 Oxidation with H 2 CrO 4 has: Formation of a chromate ester (good leaving group) An antiperiplanar H on the ! carbon A "base" that attacks to form the C=C double bond " ! R OH H H H 2 CrO 4 R O H H Cr OH O O H 2 O Cr(6+) R O H + H 2 CrO 3 Cr(4+) 2. Show the required calculations for the oxidation step of the lab. You should show: the Show the required calculations for the oxidation step of the lab....
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