Treatment of compound E (molecular formula C4H8O2) with excess CH3CH2MgBr yields

Chapter 20, Problem 20.76

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Treatment of compound E (molecular formula C4H8O2) with excess CH3CH2MgBr yields compound F (molecular formula C6H14O) after protonation with H2O. E shows a strong absorption in its IR spectrum at 1743 cm1. F shows a strong IR absorption at 3600 3200 cm1. The 1 H NMR spectral data of E and F are given. What are the structures of E and F? Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4 H), and 1.55 (singlet, 1 H) ppm

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