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Compound F, C5H8O, has an 1H-NMR spectrum that exhibits absorption in the alkane region (1 to...

Compound F, C5H8O, has an 1H-NMR spectrum that exhibits absorption in the alkane region (1 to 2 δ) and shows a triplet at 2.8 δ. Treatment of F, first with aqueous acid and then with KMnO4, yields pentanedioic acid. (KMnO4 cleaves 1,2-diols to yield carboxylic acids.) Propose a structure for compound F.

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