Problem: Compound A has molecular formula C5H10. When A is treated with BH3, followed by H2O2, NaOH, H2O, a mixture of B and B’ is isolated. B and B’ each have molecular formula C5H12O. Separately, B and B’ are optically active. A 50:50 mixture of B and B’ is optically inactive, however. When the mixture of B and B’ is exposed to the Jones reagent (CrO3, H2SO4, H2O), a single compound C (C5H10O) is produced. Finally, when A is treated with O3 followed by H2O2, acetone (shown below) and Compound D (C2H4O2) are produced. Complete the reaction scheme below by drawing structures for the unknown compounds A, B, B’, C and D. Be sure to show the stereochemistry of B and B’ clearly and unambiguously!

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Compound A has molecular formula C5H10. When A is treated with BH3, followed by H2O2, NaOH, H2O, a mixture of B and B’ is isolated. B and B’ each have molecular formula C5H12O. Separately, B and B’ are optically active. A 50:50 mixture of B and B’ is optically inactive, however. When the mixture of B and B’ is exposed to the Jones reagent (CrO3, H2SO4, H2O), a single compound C (C5H10O) is produced. Finally, when A is treated with O3 followed by H2O2, acetone (shown below) and Compound D (C2H4O2) are produced. Complete the reaction scheme below by drawing structures for the unknown compounds A, B, B’, C and D. Be sure to show the stereochemistry of B and B’ clearly and unambiguously!

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