Question

Systematically deduce the structure of the organic compound from the given data. Interpret all the
spectral data to the deduced structure. 15*5 = 25 marks)
(1) Molecular formula: C.H.NO, H NMR (CDC) 8:4.3 (quartet, 2H, J = 7.5 Hz), 3.5 15, 2H), 1.3
(triplet, 3H, J = 7.5 Hz]: C NMB (CDC) & 165, 115, 52, 25, 15.
(2) Molecular formula CH, O, H NMR (CDI) 0:3,7 (s), 1.2 (s) [1:3 ratio integration): "C NMR
(CDCI) 8: 180, 52, 39, 28
(3) Molecular formula: CH,,
NH NMR (CDCI) 8:2.6 (quartet, 2H, J = 7.0 Hz), 2.2 (s. 6H), 1.1 (triplet,
3H, ) = 7 0 Hz); C NMR (CDC) : 55, 48, 15.
(4) Molecular formula: CH.NO, H NMR (CDCI) 8: 8.2 and 7.8 (AA BB pattem, 4H, J = 8.0 Hz), 4.5
(quartet, 2H, J = 7.5 Hz), 1.4 (triplet, 3H, J = 7.5 Hz): "C NMR (CDCL) 8: 165, 135, 132, 130, 62, 18; IR:
2250, 1724 cm
(5) Molecular formula: C.H.CIO, 'H NMR (CDCI) 8: 7.95 (doublet, 2H, J = 7.6 Hz), 7.60 (triplet, 1H, ) =
7.6 Hz), 7.50 (triplet, 2H, J = 7.6 Hz), 3.95 (triplet, 2H, 1 = 8.0 Hz), 3.45 (triplet, 2H, J = 8.0 Hz): -C NMR
(CDCI) 8: 195, 135, 132, 130, 129, 41, 38; R: 1686 cm.​

Answer 1

Explanation:

"Hz" (and any subsequent words) was ignored because we limit queries to 32 words.