Q10(a). Structure from UV, IR, NMR and mass spectra: C₁₂H₁₄O₄
Giving proper explanation, deduce the structure of the organic compound with molecular formula C₁₂H₁₄O₄ with the following spectral data: UV, λmax nm: 230 (ε 10 000); IR, ν cm⁻¹: 3040 (w), 2980 (w), 2880 (w), 1715 (s), 1600 (m), 1580 (m), 1450 (m), 1375 (m), 1280 (s), 1070 (s), 740 (s); ¹H NMR, δ: 1.31 (t, J = 7 Hz, 6H), 4.4 (q, J = 7 Hz, 4H), 7.64–7.98 (m, 4H); MS (m/z): 222, 177, 149, 121.
Answer in brief
Diethyl benzene-1,2-dicarboxylate (diethyl phthalate), o-C₆H₄(COOC₂H₅)₂.
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Coversstructure elucidationdiethyl phthalatecombined spectroscopym/z 149
All parts of Question 10
- 10(a) Structure from UV, IR, NMR and mass spectra: C₁₂H₁₄O₄10 marks
- 10(b) Dimer of cyclopentadiene; a [1,3] shift of carbon with inversion10 marks
- 10(c) Urea, amine and carbamate from benzoic acid (Curtius route)10 marks