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From the molecular formula, the compound has "six degrees of unsaturation" (six double bonds, carbonyls or rings). The large number suggests the presence of an aromatic ring (DU = 4).
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Click here for a review of 13C spectroscopy.
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The 13C spectrum contains nine peaks, indicating that the molecule has some elements of symmetry. The quartet at 
14 and the triplet at 60 represent a simple CH3 and a CH2 which is deshielded by an electronegative atom (most likely oxygen); the doublet at 58 and the triplet at 36 are CH and CH2 groups which are adjacent to one or more electronegative groups. The peaks at 141 - 125 are in the aromatic region; the fact that three doublets and one singlet are observed strongly suggests monosubstitution.
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Click here for a review on Infrared Spectroscopy.
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The mass spectrum displays a molecular ion, an m-45 and a peak at m/e = 91, all of which are consistent with a molecule containing benzyl and ethoxy groups.
The 13C spectrum contains six peaks, indicating that the molecule has some elements of symmetry. The quartet at
The proton NMR also shows evidence for two ethyl groups, a CH-CH2- group, and a monosubstituted aromatic group; the chemical shift suggests that the carbons of the CH-CH2- adjacent to one or more electronegative groups.
The IR is consistent with an aromatic compound containing a carbonyl group.
The simplest structure which is consistent with all of these data would be an aromatic compound linked via a -CH2CH group to a diethyl ester.
The proton NMR has a coupled quartet and a triplet, consistent with an ethyl group in which the CH2 (at 4.1) is adjacent to an electronegative atom (most likely oxygen). The presence of a coupled triplet and doublet suggests the presence of a CH-CH2- group in which both carbons are adjacent to one or more electronegative atoms. The singlet at 7.1 is consistent with a monosubstituted aromatic compound.
3400-3200 cm-1: no OH peak
3100 cm-1: small peak, suggesting unsaturated CH
2900 cm-1: strong peak suggesting saturated CH
2200 cm-1: no unsymmetrical triple bonds
1730 cm-1: strong carbonyl
1610 and 1500 cm-1: weak peaks, vaguely consistent with aromatic carbon-carbon double bonds
The molecule contains four oxygens, and from the analysis, contains six double bonds, carbonyls or rings. The large number of degrees of unsaturation strongly suggests an aromatic compound (DU = 4). 56 and the triplet at 71 represent a CH3 and a CH2 group which are deshielded by electronegative atoms (most likely oxygen); the peaks at 161 - 128 are in the aromatic region; the fact that three doublets and one singlet are observed strongly suggests monosubstitution.
