HW #16 - the isolated compounds are each optically active ....

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MWF 12:00 Section – Bocknack CH 310M/318M Fall 2008 UTEID: Please submit to the correct slot in the collection box outside WEL 2.212!!! Last Name: First Name: Score: Graded Homework Problem #16 Deadline : 3:00 p.m., Monday, 11/10/08 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 7 H 12 ) is exposed to aqueous Hg(OAc) 2 followed by NaBH 4 , a single product, B (molecular formula C 7 H 14 O), can be isolated after this reaction. B is optically inactive . When A is treated with OsO 4 , followed by NaHSO 3 , a mixture of two products, C and D , is isolated. C and D both have molecular formula C 7 H 14 O 2 . The mixture of C and D is optically inactive, but when C and D are separated from each other,
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Unformatted text preview: the isolated compounds are each optically active . Finally, when A is exposed to O 3 , followed by (CH 3 ) 2 S, the only product isolated is 5-oxoheptanal (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 7 H 12 ) B (C 7 H 14 O) (optically inactive) 1) OsO 4 2) NaHSO 3 C (C 7 H 14 O 2 ) (optically active) (optically active) The mixture of C and D is optically inactive 1) O 3 2) (CH 3 ) 2 S 5-Oxoheptanal + 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 O H O D (C 7 H 14 O 2 )...
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This note was uploaded on 09/14/2009 for the course CH 310 N taught by Professor Blocknack during the Fall '08 term at University of Texas at Austin.

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