HW17Key - Graded Homework Assignment #17 Answer Key...

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Graded Homework Assignment #17 – Answer Key Deadline : 9:00 a.m., Friday, 4/16/10 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This assignment is worth a total of 40 raw points. 1. (20 points; each box is worth 5 points) When an unknown hydrocarbon A (molecular formula C 8 H 14 ) is exposed to HCl, a single product, B (molecular formula C 8 H 15 Cl), can be isolated after the reaction is complete. B is optically inactive . When A is treated with BH 3 , followed by H 2 O 2 , NaOH, H 2 O, a mixture of two products, C and D , is isolated. C and D both have molecular formula C 8 H 16 O. The mixture of C and D is optically inactive, but when C and D are separated from each other, the isolated compounds are each optically active . Finally, when A is exposed to O 3 , followed by H 2 O 2 , the only product isolated is 6-oxooctanoic acid (structure shown below). Given this information, propose structures for the unknown compounds A , B , C , and D . Write your answers in the appropriate boxes in the reaction scheme provided below. Be sure to show stereochemistry clearly
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This note was uploaded on 10/25/2010 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas.

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HW17Key - Graded Homework Assignment #17 Answer Key...

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