2-Methylpentanal and 4-methyl-2-pentanone are constitutional isomers with the mo

Question

2-Methylpentanal and 4-methyl-2-pentanone are constitutional isomers with the molecular formula C_6 H_12 O. Each shows a molecular ion peak in its mass spectrum at m/z 100. Spectrum A shows significant peaks at m/z 85, 58, 57, 43, and 42. Spectrum B shows significant peaks at m/z 71, 58, 57, 43, and 29. Assign each compound its correct spectrum (showing the fragments and their m/z values). Treatment of compound E (molecular formula C_4 H_8 O_2) with excess Ethyl magnesium bromide (step 1) yields compound F (molecular formula C_5 H_14 O) after protonation with H_2 O (follows step 1 as step 2 to form Cmpd F). E shows a strong absorption in its IR spectrum at 1743 cm^-1. F shows a strong IR absorption at 3200-3600 cm^-1. The ^1 H NMR spectral data of E and F are given. What are the structures of E and F?

Explanation / Answer

2-Methylpentanal and 4-methyl-2-pentanone are constitutional isomers with the mo

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