PHR-410
Assignment (Sample)
1. Routine operations:
➢ From the molecular ion, the molecular weight is 198/200. The molecular ion has
two peaks of approximately equal intensity separated by two mass units. This is the
characteristic pattern for a compound containing one bromine atom.
➢ The molecular formula is C9H11Br so one can determine the degree of unsaturation.
Replace the Br by H to give an effective molecular formula of C9H12 (CnHm) which
gives the degree of unsaturation as (n - m/2 +1) = 9 - 6 + 1 =4.
➢ The total integral across all peaks in the 1H spectrum is 43 mm. From the molecular
formula, there are 11 protons in the structure, so this corresponds to 3.9 mm per
proton. The relative numbers of protons in different environments:
➢ This analysis gives a total of 5+2+2+2 = 11 protons which is consistent with the
molecular formula provided.
➢ From the 13C spectrum there are 7 carbon environments: 4 carbons are in the typical
aromatic/olefinic chemical shift range and 3 carbons in the aliphatic chemical shift
range.
➢ From the 13C DEPT spectrum there are 3 x CH resonances in the aromatic/olefinic
chemical shift range and 3 x -CH2- carbons in the aliphatic chemical shift range
2. Identification of structural elements:
➢ There is no useful additional information from the infrared spectrum.
➢ In the mass spectrum there is a strong fragment at m/e = 91 and this indicates a
possible Ph-CH2- group.
➢ The ultraviolet spectrum shows a typical benzenoid absorption without further
conjugation or auxochromes. This would also be consistent with the Ph-CH2-
group.
➢ From the 13C NMR spectrum, there is one resonance in the 13C {'H} spectrum which
13
does not appear in the C DEPT spectrum. This indicates one quaternary (non-
13
protonated) carbon. There are 4 x C resonances in the aromatic region, 3 x CH
and 1 x quaternary carbon, which is typical of a monosubstituted benzene ring.
➢ From the 'H NMR, there are 5 protons near 5 ~7.2 which strongly suggests a
monosubstituted benzene ring. The Ph-CH2- group is confirmed.
➢ The triplet at approximately δ 3.3 of intensity 2H suggests a -CH2- group. The
downfield chemical shift suggests a -CH2- X group with X being an electron
withdrawing group (probably bromine). The triplet splitting indicates that there
must be another -CH2- as a neighbouring group.
➢ The triplet at approximately 8 2.8 ppm of intensity 2H in the 1H NMR spectrum
suggests a -CH2- with one -CH2- as a neighbour.
➢ The quintet at approximately 8 2.2 of intensity 2H is consistent with a -CH2- group
coupled to two flanking -CH2- groups. A sequence -CH2-CH2-CH2- emerges in
agreement with the 13C data.
➢ Thus, the structural elements are:
i. Ph-CH2-
ii. -CH2-CH2-CH2-
iii. -Br
3. Assembling the Structural Elements
➢ Clearly there must be some common segments in these structural elements since
the total number of C and H atoms adds to more than is indicated in the molecular
formula. One of the -CH2- groups in structural element (2) must be the benzylic -
CH2- group of structural element (1).
➢ The structural elements can be assembled in only one way, and this identifies the
compound as 1-bromo-3-phenylpropane.