Assignment 4 (25 marks)

Systematically deduce the structure of the organic compound from the given data. Interpret all the
spectral data to the deduced structure. (5 x 5 = 25 marks)

(1) Molecular formula: C6H12O2, 1H NMR (CDCl3) : 3,7 (s), 1.2 (s) [1:3 ratio integration]; 13C NMR
(CDCl3) : 180, 52, 39, 28.

(2) Molecular formula: C4H11N, 1H NMR (CDCl3) : 2.6 (quartet, 2H, J = 7.0 Hz), 2.2 (s, 6H), 1.1 (triplet,
3H, J = 7.0 Hz); 13C NMR (CDCl3) : 55, 48, 15.

(3) Molecular formula: C9H9ClO, 1H NMR (CDCl3) : 7.95 (doublet, 2H, J = 7.6 Hz), 7.60 (triplet, 1H, J =
7.6 Hz), 7.50 (triplet, 2H, J = 7.6 Hz), 3.95 (triplet, 2H, J = 8.0 Hz), 3.45 (triplet, 2H, J = 8.0 Hz); 13C
NMR (CDCl3) : 195, 135, 132, 130, 129, 41, 38; IR: 1686 cm-1.

(4) Molecular formula: C5H7NO2, 1H NMR (CDCl3) : 4.3 (quartet, 2H, J = 7.5 Hz), 3.5 (s, 2H), 1.3
(triplet, 3H, J = 7.5 Hz); 13C NMR (CDCl3) : 165, 115, 62, 25, 15.

(5) Molecular formula: C10H9NO2, 1H NMR (CDCl3) : 8.2 and 7.8 (AA’BB’ pattern, 4H, J = 8.0 Hz), 4.5
(quartet, 2H, J = 7.5 Hz), 1.4 (triplet, 3H, J = 7.5 Hz); 13C NMR (CDCl3) : 165, 135, 132, 130, 62, 18; IR:
2250, 1724 cm-1.

END of ASSIGNMENT