Diane Diol worked for several days to prepare the following compounds: She labeled them carefully and went
Question:
She labeled them carefully and went to lunch. To her horror, when she returned, she found that the labels had fallen off the bottles and onto the floor. Gladys Glycol, the student at the next bench, told her that the diols could be easily distinguished by two experiments. All Diane had to do was determine which ones were optically active and how many products were obtained when each was treated with periodic acid. Diane did what Gladys suggested and found the following to be true:
1. Compounds A, E, and F are optically active, and B, C, and D are optically inactive.
2. One product is obtained from the reaction of A, B, and D with periodic acid.
3. Two products are obtained from the reaction of F with periodic acid.
4. C and E do not react with periodic acid.
Will Diane be able to distinguish among the six diols and label them from A to F with only the preceding information? Label the structures.
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