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QUESTION

Ozonolysis of A followed by dimethyl sulfide reduction produces a single optically active compound C, C5H8O2.

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?

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