30. A compound with IR bands at 3025 (m), 2915 (s), 2830 (m). 2705 (m), 1725 (s)

Question

30. A compound with IR bands at 3025 (m), 2915 (s), 2830 (m). 2705 (m), 1725 (s), 1645 (w) cm,; and has 7 peaks in the 13C NMR including peaks at 124, 129 and 205 ppm. DEPT 90: 124t. 129 and 205 t. (2 points) Answer- 31 A compound with IR bands at 1745 (s), 1220 (s) crm-1; 1H NMR: 4H), 13C:3 peaks including one at 171 ppm. (2 points) 2.10 (s, 6H), 4.25 (s. Answer . 32. A compound with an IR bands at 3450 (s. brd), 1705 (s) cm·1·"H NMR: 1.25 (s,6H). 2.20 (s,3H). 2.60 (s,2H), 3.90 (s,1H, exc with D20). (2 points) Answer 33. A compound with an IR band at 1735 (s) cm: 6 13C NMR peaks including one at 177 ppm; is chiral when pure. (2 points) Answer 34. A compound with an IR band at 2250 (s) cm, 'H NMR: 8 1.45 (d, 3H), 3.05 (sextet. 1 H). 3.7 (d, 2H); mass spec: mZ = 103,105 (3:1). (2 points) Answer 35. A compound with 1H NMR peaks at 090 (d, 6H), 1.05 (d. 3H), 1.35 (s, 2H, exc with D2O), 2.80 (pentet, 1H): 4 peaks in the C NMR: mass spec 87. (2 points) Answer -

Explanation / Answer

The key starting material 2-propyl-4H- 3,1-benzoxazin-4-one (2) has been synthesized via the interaction of butyroyl chloride with anthranilic acid in the presence of pyridine which yielded the corresponding anthranil 1. Treatment of anthranil 1 with acetic anhydride afforded the benzoxazinone 2. The structure of anthranil 1 was proved from its microanalytical data and its IR spectra (cm -1 ) which showed strong absorption bands at 1672, 1693, 3286 and 3422 attributable to max of two carbonyl groups, NH and OH respectively. IR spectrum of the benzoxazinone 2 exhibits strong absorption bands at 1614, 1764 (cm -1 ) due to max .of C=N and C=O and lack of any band for NH and / or OH such IR data agreed well with the proposed structure.The 3-amino-2- propylquinazolin-4(3H)-one (3) resulted via treatment of the Benzoxazinone 2 with hydrazine hydrate in boiling ethanol. The structure of compound 3 was confirmed based on its elemental and spectral analyses, thus IR spectrum of compound 3 reveals strong absorption band at 1596, 1673, 3309 and 3212 attributable to max for C=N, C=O and NH 2 . EIMS of compound 3 exhibits an ion peak at m/z (M + ,203). 1 HNMR spectrum of compound 3 exhibits (ppm) in CDCl 3 1 (t,3H,CH 3 ), 1.8(m, 2H,CH 2 Me), 2.8(t, 2H, CH 2 Q), 7.2-8 (m, 4H, aromatic), 9.3(s, 2H, NH 2 ).

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