To answer the questions 23 and 24 below, consider the following information: an

Question

To answer the questions 23 and 24 below, consider the following information: an abanod laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: C1112 Government agents have offered you a considerable sum to determine the structure of compound After verifying the molecular formula by elemental analysis, you find that Compound A racts with mol cquiv of hydrogen and, after treatment with acidic KMnO, gives the dicarboxylic acid C tsce below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with I mol equiv of hydrogen, but yields eyclohexanone a after treatment with acidic KMnO C-OH CHy Compound C cyclohez anone 23. Suggest structures for A and B 24. What was the other product formed in the KMn04 oxidation of B? 25. Povidone is produced commercially as a series of products having mean molecular weights ranging from about 10,000 to 700,000. Complexed with iodine, povidone yiclds an iodophor, marketed under the tradename Betadine, which is used as a topical anti-infective. 2 Identify the

Explanation / Answer

23.) Structure of compound A is HO-CH2CH(CH3)CH=CHCH2CH2-OH ,It will react with the 1 eq H2 gas to form HO-CH2CH(CH3)CH2CH2CH2CH2-OH and finally with acidic KMnO4 solution it forms HOOCCH(CH3)CH2CH2CH2COOH .

Structure of Compound B is Cyclohex2,3-an1-ol . It will react with 1 eq H2 gas to form Cyclohexanol which when react with acidic KMnO4 forms Cyclohexanone.

24.)The other product which might form is that is very strong oxidation of the Cyclohexanone to Dicarboxylic acid that is it will rupture the ring structure and will form Hexane1,6-dioic acid .

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