HW04 - Bocknack CH 310N Spring 2010 Please submit to the...

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Bocknack CH 310N Spring 2010 UTEID: Please submit to the correct slot in the collection box outside WEL 2.212!!! Last Name: First Name: Score: Graded Homework Assignment #04 Deadline : 2:00 p.m., Friday, 2/5/10 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This assignment is worth a total of 40 raw points. Each question is worth 20 points. 1. (20 points) Compound A has molecular formula C 6 H 12 . When A is exposed to Br 2 , the red color disappears. When A is treated with BH 3 followed by H 2 O 2 , NaOH, H 2 O, a mixture of X and X’ is isolated. X and X’ are enantiomers of each other, and each has molecular formula C 6 H 14 O. Compound B (C 6 H 12 O) is formed as the only product if X or X’ is exposed to K 2 Cr 2 O 7 /H 2 O/H 2 SO. 1 H and 13 C NMR data for Compounds A and B are listed below. All chemical shifts are reported in units. The relative integration and multiplicity of each 1 H NMR signal are listed after each chemical shift. For Compound B only, 1 H NMR coupling constants are also provided.
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