i.            Suggest a possible structure for the hydrocarbon C6H14, which has the infrared spectrum shown here: Is there more than one correct structure?

ii.            The hydroxylamine I can be oxidized by MnO2 to the amide oxohaemanthidine (II). In dilute solution, the carbonyl absorption band of II occurs at 1702 cm1 . Explain this observation.

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iii.            The infrared spectra of the three xylene (dimethylbenzene) isomers, and an additional aromatic hydrocarbon, are given below. Assign the spectra to the isomers and suggest a potential structure for the remaining unknown substance.

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iv.            The COH stretching mode of chloroform (CHCl3), which occurs at 3022 cm1 , is one of the rare exceptions to the 3000-cm1 rule. What is the rule? Suggest an explanation for this exception.

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