Problem: Compounds A and B each have molecular formula C6H12. When A or B is exposed to H2 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 (C6H13Br), is obtained as the major product. When A or B is treated with O3 followed by (CH3)2S, the same mixture of products is obtained. This mixture is comprised of compound D, which has molecular formula C4H8O, and compound E, which has molecular formula C2H4O. When A is treated with BH3, followed by H2O2, NaOH, H2O, the chiral alcohol indicated in the reaction scheme below is obtained as a racemic mixture. When B is treated with BH3, followed by H2O2, NaOH, H2O, a different chiral alcohol is 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!

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Compounds A and B each have molecular formula C6H12. When A or B is exposed to H2 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 (C6H13Br), is obtained as the major product. When A or B is treated with O3 followed by (CH3)2S, the same mixture of products is obtained. This mixture is comprised of compound D, which has molecular formula C4H8O, and compound E, which has molecular formula C2H4O. When A is treated with BH3, followed by H2O2, NaOH, H2O, the chiral alcohol indicated in the reaction scheme below is obtained as a racemic mixture. When B is treated with BH3, followed by H2O2, NaOH, H2O, a different chiral alcohol is 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!

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