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Draw the structures of compounds

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Compound A (C7H14O2) is chiral and shows a peak at 170 ppm in the 13C NMR (partial spectrum). This compound undergoes hydrolysis to give two new compounds B and C. Compound B (C4H10O) is also chiral. Compound C (C3H6O2) is not. Upon Jones oxidation (CrO3, H2SO4), compound B yields an achiral compound D. Compound D can also be prepared from compound C by the following reaction sequence: 1. SOCl2, 2. Me2CuLi. Alternatively, compound C can be converted to compound E by reaction with NaOH followed by benzoyl chloride (PhCOCl). Compound E shows two strong absorbances at 1765 and 1840 cm-1 in the IR. On the basis of this data, draw the structures of compounds A to E. Show your work for full credit.

Reference no: EM131478973

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