POD12Key - A if A is treated with H 2 CrO 4 Compound C is...

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Problem of the Day #12 – Answer Key Deadline : IN CLASS on M 8/2/2010 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Compound A (C 4 H 8 O 2 ) has the infrared spectrum given below. 1 H NMR and 13 C NMR data for this compound are listed to the right of the IR spectrum. When A is treated with Na metal, a flammable gas is produced. When A is treated with anhydrous PCC, Compound B (C 4 H 6 O 2 ) is isolated. B gives a positive iodoform test (it produces a yellow precipitate upon treatment with I 2 , KOH followed by H 3 O + ). When B is treated with Tollens’ reagent, Compound C (C 4 H 6 O 3 ) is formed. Compound C is also formed directly from
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Unformatted text preview: A if A is treated with H 2 CrO 4 . Compound C is difficult to isolate, however, because upon gentle heating it decomposes to yield CO 2 and acetone. Propose structures for Compounds A , B , and C . Write your answers in the boxes below. It is not necessary to provide an explanation for your answers. A B C (C 4 H 8 O 2 ) (C 4 H 6 O 2 ) (C 4 H 6 O 3 ) H 2 CrO 4 PCC Tollens' Na flammable gas 1) I 2 , KOH 2) H 3 O + yellow ppt heat CO 2 + acetone H 3 C OH O H 3 C H O O H 3 C OH O O 1 H NMR : disappears upon D 2 O shake), 2.70 (2H, t), 2.20 (3H, s) 13 C NMR : 209.3, 57.5, 45.9, 30.4...
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