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1) In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label compound A: C,H12. Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecule formula by elemental analysis, you find that compound A reacts with a mol equiv of hydrogen and, after treating with acid KMnO4, gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled compound B (isomer of A). Compound B also reacts with 1 mole equiv of hydrogen, but yields cyclohexanone after treatment with acid KMnO CH compound c cyclohexanone i) Suggest the structures for A and B. (8 points) ii) What are the two possible products formed if compound A reacted with Br2. (specify the stereochemistry) (6 points) ii) Which one of the two products inii) is more stable in considering the stereochemistry? (3mechnism , details!!!!!!!!!!

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CTH alkena Foll2- 3 8 Cp2- 3 8 Cp

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