POD08 - 2 CrO 4 , compound A was oxidized to an optically...

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CH s310N/s318N Summer 2007 Last Name: First Name: Dr. Bocknack UTEID: Score: Problem of the Day #08 Deadline : 3:00 p.m., Monday, 7/23/07 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Each box is worth 5 points. Compound A , C 6 H 12 O 2 , was found to be optically active, and was oxidized to an optically active carboxylic acid B , C 6 H 12 O 3 , upon treatment with Tollens’ reagent. Oxidation of A by anhydrous PCC gave an optically inactive compound, C , C 6 H 10 O 2 , that gave 3-methylpentane when subjected to the reaction conditions used for the Wolff– Kishner reduction. When treated with aqueous H
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Unformatted text preview: 2 CrO 4 , compound A was oxidized to an optically inactive dicarboxylic acid, D , C 6 H 10 O 4 . Complete the reaction scheme outlined below by proposing structures for compounds A , B , C , and D . You do not need to show stereochemistry in the structures that you draw, but you should mark any chiral centers present with an asterisk ( * ). It is not necessary to provide an explanation for your answers. 3-Methylpentane A (C 6 H 12 O 2 ) B (C 6 H 12 O 3 ) C (C 6 H 10 O 2 ) D (C 6 H 10 O 4 ) Tollens' H 2 CrO 4 H 2 O PCC H 2 NNH 2 KOH,...
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