HW16 - The mixture of C and D is optically inactive,...

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CH 310M/318M Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Please circle the section in which you are registered ! POINTS MAY BE DEDUCTED IF YOU DON’T ! MWF 9:00 TTh 8:00 Graded Homework Problem #16 Deadline : 3:00 p.m., Thursday, 4/10/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Compound A , having molecular formula C 6 H 12 , yields B , a single, achiral product, upon treatment with HCl. The molecular formula of B is C 6 H 13 Cl. When A is exposed first to BH 3 , followed by H 2 O 2 , NaOH, H 2 O, a mixture of C and D is isolated. Each of these compounds has molecular formula C 6 H 14 O. If C and D are separated from each other, the pure compounds are optically active.
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Unformatted text preview: The mixture of C and D is optically inactive, however. When A is exposed first to O 3 , followed by H 2 O 2 , the products are acetone and E (C 3 H 6 O 2 ). Finally, when A is treated with H 2 over a Pd catalyst, 2-methylpentane is formed. Propose structures for the unknown compounds A , B , C , D , and E . Write your answers in the appropriate boxes in the reaction scheme below. Be sure to show stereochemistry clearly and unambiguously where necessary! A (C 6 H 12 ) B (C 6 H 13 Cl) + C (C 6 H 14 O) D (C 6 H 14 O) + O Acetone (C 3 H 6 O) E (C 3 H 6 O 2 ) 2-Methylpentane HCl 1) BH 3 2) H 2 O 2 , NaOH, H 2 O H 2 , Pd (cat.) 1) O 3 2) H 2 O 2...
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This note was uploaded on 05/14/2009 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas at Austin.

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