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!
Frequently Asked Questions
What scientific concept do you need to know in order to solve this problem?
Our tutors have indicated that to solve this problem you will need to apply the Retrosynthesis concept. You can view video lessons to learn Retrosynthesis. Or if you need more Retrosynthesis practice, you can also practice Retrosynthesis practice problems.
What is the difficulty of this problem?
Our tutors rated the difficulty ofCompound A has molecular formula C5H10. When A is treated wi...as high difficulty.
How long does this problem take to solve?
Our expert Organic tutor, Chris took 8 minutes and 47 seconds to solve this problem. You can follow their steps in the video explanation above.