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CH223 001 HW 6 - CH223 001 HW 6...

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CH223 001 HW 6 (Daily) SHAW ROBERT H CH 223, section 001, Fall 2008 Instructor: Kay Sandberg Web Assign Current Score: 10.5 out of 11 Due: Friday, September 5, 2008 07:00 AM EDT Description This assignment corresponds to Lecture 6 and the DE presentation(s) which accompany it. Instructions The due date for this assignment is past. Your work can be viewed below, but no changes can be made. 1. 3/3 points A student added tert- butyl bromide to an aqueous ethanol solution and warmed the resulting solution. The next day he separated the compounds in solution and found there were 4 compounds - one was the original tert- butyl bromide. He performed the following techniques which provided the data given below. Use this information along with the information given in Tables 13.1 and 13.4 of your text to help you determine the structure of each product whose structure would be consistent with its corresponding information. If you do not have the suggested text, you can use any textbook's proton chemical shift table (corresponding to Table 13.1) and IR absorption frequency table (corresponding to Table 13.4). Your lab manual also contains this info. Draw the skeletal structure. (a) product 1 1 H NMR: singlet @ 4.6 singlet @ 1.7 relative integration 1:3 Diagnostic IR peak: 890 cm -1 hydrogenation: consumed some hydrogen (do not know molecular formula, so he is not sure of mole ratio of hydrogen comsumed). Consumption of hydrogen indicates the presence of at least one pi bond.
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