POD05Key - 4 , H 2 SO 4 , H 2 O. The IR spectrum of C , and...

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Problem of the Day #05 – Answer Key Deadline : 3:00 p.m., Monday, 7/16/07 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Compound A , a hydrocarbon having molecular formula C 6 H 12 , has the IR and 1 H NMR spectra shown on the next page. When A is treated with Hg(OAc) 2 , H 2 O followed by NaBH 4 , Compound B (C 6 H 14 O) is isolated as a racemic mixture. When B is treated with H 2 CrO 4 , Compound C (C 6 H 12 O) is produced. C is also isolated as the major product when Compound X (C 6 H 10 ) is treated with HgSO
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Unformatted text preview: 4 , H 2 SO 4 , H 2 O. The IR spectrum of C , and the IR and 1 H NMR spectra of X , are also given on the next page. Propose structures for the unknown compounds A , B , C , and X . Write each answer in the appropriate box below. It is not necessary to provide an explanation for your answers. YOU ONLY NEED TO TURN IN THE FIRST PAGE WHEN YOU SUBMIT YOUR ANSWERS!!!! A B C X 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 H 2 CrO 4 HgSO 4 , H 2 SO 4 , H 2 O OH O...
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