Ozonolysis of a followed by dimethyl sulfide reduction

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Ozonolysis of A followed by dimethyl sulfide reduction produces a single optically active compound C, C5H8O2. Reduction of C with ethereal LiAlH4 affords optically active compound D (C5H12O2) of the (S)-configuration. The 13C NMR spectrum of D is shown below. What are the structures of A-D?

Reference no: EM13384950

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