Click on any peak for help in interpreting this spectrum.
There are two doublets in this group with a total area of 4 hydrogens, indicating two pairs of CH groups, each adjacent to one non-equivalent proton. The chemical shift (d 7.2) is in the aromatic region, and this type of pattern is highly characteristic of an unsymmetrical, 1,4-disubstituted benzene derivative.
The peak is a singlet, area 3, indicating that it corresponds to an isolated methyl group. The chemical shift (d 2.25) suggests that the hydrogen is adjacent to an electronegative group.
The peak is a doublet, area 6, indicating that it corresponds to six identical hydrogens (two CH3 groups) adjacent to one hydrogen. The chemical shift (d 1.2) is in the "simple alkane" region.
The peak is a quartet, indicating that it corresponds to a methyl group. The chemical shift (d 22) is in the "simple alkane" region.
The peak is a singlet, indicating that it corresponds to a carbon with no attached hydrogens. The chemical shift (d 117) is in the alkene region, or could correspond to as sp-hydridized carbon, adjacent to an electronegative group.
This group of peaks is in the aromatic region, with the exception of the singlet at 109 ppm, which is shifted down due to a "shielding" effect of an attached group. The fact that there are four peaks, two doublets and two singlets, suggests 1,4-disubstitution on a benzene ring.
The spectrum seems to be consistent with an aryl nitrile.
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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The 13C spectrum contains six peaks, indicating that the molecule has some elements of symmetry. The quartet at d 22 represents a simple CH3 which is deshielded slightly by an electronegative group. The peaks at d 142 - 129 are in the aromatic region; the fact that two doublets are observed strongly suggests 1,4-disubstitution. The two singlets at 110 and 117 are somewhat anomalous, and overlap the double bond and nitrile regions. The peak at 110 could represent the aromatic carbon, strongly shielded by the nitrile group.
3400 cm-1:
no OH or NH present
3100 cm-1:
sharp peak suggesting sp2 CH 2900 cm-1:
strong peak indicating sp3 CH
2200 cm-1:
strong triple bond stretch 1710 cm-1:
no carbonyl absorbance
1610 cm-1:
several peaks suggesting Ar C=C
Click on any numbered peak for help in interpreting this spectrum.
The peak occurs at m/e = 90, making this peak m-27 (loss of HCN).
The peak occurs at m/e = 117, which is the molecular weight of the compound, making this the molecular ion (m.+); it is also the base peak in this spectrum (the most intense peak).
The peak occurs at m/e = 87, making this peak m-1 (loss of a hydrogen). Loss of a m/e = 1 is often seen in compounds with acidic hydrogens.
The peak occurs at m/e = 88, which is the molecular weight of the compound, making this the molecular ion (m.+).
The mass spectrum consists of a molecular ion at 117, which is the base peak, and a m-27 peak at 90. The peak at 91 is low intensity, and it is unlikely that is represents a benzyl unit. The mass lost corresponds to HCN. The spectrum is consistent with a molecule containing a nitrile group.
C8H7N; MW = 117.15
The proton NMR has a singlet at d 2.2 and a pair of doublets at 7.2. The doublets in the aromatic region strongly suggest a 1,4-disubstituted aromatic compound; the peak at d 2.2 must represent a methyl group which is somewhat deshielded, perhaps attached to the ring.
IUPAC Name: (4-methylphenyl)methanenitrile (p-toluonitrile)
13C NMR: 
MS: 