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POD04 - Propose structures for the unknown compounds A B C...

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CH s310N/s318N Summer 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Problem of the Day #04 Deadline : 3:00 p.m., Friday, 7/18/08 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 first with BH 3 , followed by H 2 O 2 , NaOH, H 2 O, Compound B (C 6 H 14 O) is isolated. When B is treated with anhydrous PCC, 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 first with (sia)2BH, followed by H 2 O 2 , NaOH, H 2 O. The IR spectrum of B , and the IR and 1 H NMR spectra of X , are also given on the next page.
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Unformatted text preview: 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 (C 6 H 12 ) 1) BH 3 2) H 2 O 2 , NaOH, H 2 O anhydrous PCC B (C 6 H 14 O) X (C 6 H 10 ) 1) (sia) 2 BH 2) H 2 O 2 , NaOH, H 2 O C (C 6 H 12 O) 1 H NMR of A 1H dd dd = doublet of doublets 9H singlet IR of A IR of B IR of X 1 H NMR of X 1H singlet 1H dd 1H dd 4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500 9H singlet...
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