HW16Key - obtained also as a racemic mixture The products...

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Bocknack CH 310M/318M Fall 2009 Graded Homework Problem #16 – Answer Key Deadline : 3:00 p.m., Monday, 11/9/09 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Each box is worth 4 points. Compounds A and B each have molecular formula C 6 H 12 . When A or B is exposed to H 2 over a Pd catalyst, the only product isolated is 3-methylpentane. When A or B is treated with HBr, the same optically inactive compound, C (C 6 H 13 Br), is obtained as the major product. When A or B is treated with O 3 followed by (CH 3 ) 2 S, the same mixture of products is obtained. This mixture is comprised of compound D , which has molecular formula C 4 H 8 O, and compound E , which has molecular formula C 2 H 4 O. When A is treated with BH 3 , followed by H 2 O 2 , NaOH, H 2 O, the chiral alcohol indicated in the reaction scheme below is obtained as a racemic mixture. When B is treated with BH 3 , followed by H 2 O 2 , NaOH, H 2 O, a different chiral alcohol is
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Unformatted text preview: obtained, also as a racemic mixture. The products obtained from hydroboration-oxidation of A are diastereomers of the products obtained from hydroboration-oxidation of B . Complete the reaction scheme given below by proposing structures for the unknown compounds A , B , C , D , and E . For full credit, stereochemistry needs to be shown clearly and unambiguously where indicated! 3-Methylpentane SHOW STEREOCHEMISTRY!!! SHOW STEREOCHEMISTRY!!! A (C 6 H 12 ) B (C 6 H 12 ) C (C 6 H 13 Br) + D (C 4 H 8 O) E (C 2 H 4 O) H 2 , Pd (cat.) H 2 , Pd (cat.) HBr HBr 1) O 3 1) O 3 2) (CH 3 ) 2 S 2) (CH 3 ) 2 S 1) BH 3 1) BH 3 2) H 2 O 2 , NaOH, H 2 O 2) H 2 O 2 , NaOH, H 2 O CH 3 OH + CH 3 OH (50%) (50%) CH 3 OH + CH 3 OH (50%) (50%) ( E ) stereochemistry must be shown clearly!!! Br H 3 C ( Z ) stereochemistry must be shown clearly!!! O O CH 3 H...
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