Treatment of compound C (molecular formula C4H8O) with C6H5MgBr, followed by H2O, affords compound D (molecular formula C10Hl4O). Compound D has a strong peak in its IR spectrum at 3600-3200 cm-1. The 1H NMR spectral data of C and D are given. What are the structures of C and D?
Compound C signals at 1.3 (singlet, 6 H) and 2.4 (singlet, 2 H) ppm
Compound D signals at 1.2 (singlet, 6 H), 1.6 (singlet, 1 H), 2.7 (singlet, 2 H), and 7.2 (multiplet, 5 H) ppm
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