4

H3C

CH3

CH3

H3C

H3C

CH3 C CH3 , CH3 C C CH3 , H3C

CH3

CH3

B.Sc. III (Vth Semester)

CH3

H3C

CH3
CH3

(b) C8H18. The only isomer corresponding to this molecular formula which has all 18 protons
equivalent is 2, 2, 3, 3-tetramethylbutane.
(c) C2H4Br2. The only isomer corresponding to this molecular formula which has all 4 protons
equivalent is 1, 2-dibromoethane (CH2BrCH2Br).
(d) C2H6O. The only isomer corresponding to this molecular formula which has all 6 protons
equivalent is dimethyl ether or methoxy methane (CH3OCH3).
(e) C6H6. The only isomer corresponding to this molecular formula which has all 6 protons equivalent
is benzene.
(f) C12H18. The only isomer corresponding to this molecular formula which has all 4 protons
equivalent is 1, 2, 3, 4, 5, 6-hexamethylbenzene.
Solved Problem 3. Find the structure of the compound whose PMR spectrum shows a singlet
at -912 (-088), and another singlet at -272 (-728). The ratios of the areas under the peaks
is 9 : 5 and molecular formula of the compound is C10H14.

Solution. From the information provided by the PMR spectrum we find that since there are two
peaks so the compound possess two sets of equivalent protons. These are marked as a and b.
From the ratio of areas under the peaks we know that one set comprises of nine protons (marked
as b and are represented by three methyl groups attached to the same carbon) and other set comprises
of 5 protons (marked as a and are part of the aromatic ring).
The position of the peaks tell us that the set having 9 protons must be alkyl and the set having 5
protons must be aryl. Only alkyl group which has 9 equivalent protons is tert-butyl. The signal
corresponding to it must be upfield which is indicated by its position i.e. -912 (-088). The position
of the other signal i.e. -272 (-728) indicates it to be phenyl.
Since both the signals are singlets thus there is no coupling between two types of protons. On
combining the above facts we can assign the following structrue to the compounds.
a
a
b
H
H CH
3
b
a
C CH3
H
b
a
CH
a
3
H
H
The name of the compound will be methylcumene or tert-butylbenzene or 1-methyl-1-phenylpropane.
Solved Problem 4. Find the structure of the compound whose PMR spectrum shows four
singlets i.e. at -89 (-11), -79 (-21), -74 (-26) and -61 (-39). The ratios of the areas
under the peaks is 6 : 3 : 2 : 1 and molecular formula of the compound is C6H12O2.

Solution. From the data it is clear that following structural features are present in the compound:
(i) Since there are four signals so there are four sets of equivalent protons or four types of protons.

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