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HWKey (16) - (structure shown below Given this information...

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Problem of the Day #15 – Answer Key Deadline : 3:00 p.m., Wednesday, 7/2/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When an unknown hydrocarbon A (molecular formula C 8 H 16 ), is exposed to Cl 2 , the Cl 2 rapidly disappears, and a mixture of two products, B and C , is isolated. B and C each have molecular formula C 8 H 16 Cl 2 . The mixture of B and C is optically inactive, but when B and C are separated from each other, the isolated compounds are each optically active . When A is treated with OsO 4 , followed by NaHSO 3 , a single product D (C 8 H 18 O 2 ) can be isolated. D is optically inactive . Finally, when A is exposed to O 3 , followed by H 2 O 2
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Unformatted text preview: (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 and unambiguously in all of the structures that you draw! A (C 8 H 16 ) Cl 2 D (C 8 H 18 O 2 ) (optically inactive) 1 ) O s 4 2 N a H S 3 B (C 8 H 16 Cl 2 ) (optically active) The mixture of B and C is optically inactive 1) O 3 2) H 2 O 2 O 2-Butanone + C (C 8 H 16 Cl 2 ) (optically active) O H H 3 C CH 3 OH Cl Cl CH 3 CH 3 H 3 C H 3 C Cl Cl...
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