POD11 - Compound C is also formed directly from A if A is...

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CH s310N/s318N Summer 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Problem of the Day #11 Deadline : 3:00 p.m., Thursday, 7/31/08 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.
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Unformatted text preview: Compound C is also formed directly from 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 1 H NMR : 3.84 (2H, t), 3.40 (1H, s, 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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This note was uploaded on 09/14/2009 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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