B.Sc.

III (Vth Semester)

a
CH3

a
CH3
c
b
CH CH2

a
CH3

Br

1-Bromo-2-methylpropane

a
CH3
C

a
CH3

Br

2-Bromo-2- methylpropane

The only structure that satisfies the PMR spectrum for the compound corresponds to 1-Bromo-2methylpropane.
Solved Problem 5. An aromatic hydrocarbons (molecular mass 134) exhibits the following
PMR data: (i) a doublet at -088 (6H) ; (ii) a multiplet at -186 (1H), (iii) a doublet at -245
(2H) ; (iv) a singlet at -712 (5H). Assign a suitable structure to the hydrocarbon.
Solution. From the PMR data it is clear that the given compound has 14 hydrogen atoms. This
means out of the total mass of the molecule i.e. 134, 14 units come from hydrogens. The remaining
mass i.e. 134 14 = 120 comes from carbons. Since the atomic mass of carbon is 12 units therefore the
number of carbons in the compound will be 120/12 = 10. This means the molecular formula of the
compound will be C10H14.
As there are four signals this means the compound has four sets of equivalent protons.
The first signal (-088) which is a doublet and its area correspond to 6 H must be due to two
methyl groups attached to methine carbon i.e. CH(CH3)2. These are marked as a.
The second signal (-186) which is a multiplet and its area correspond to 1 H must be due to one
methine carbon having two methyl groups and one methylene group attached i.e. CH2CH(CH3)2.
This is marked as b.
The third signal (-245) which is a doublet and its area correspond to 2 H must be due to one
methylene attached to benzene ring on one side and methine group on the other side i.e. C6H5CH2
CH. These are marked as c.
The fourth signal (-712) which is a singlet and its area correspond to 5 H must be a phenyl group
i.e. C6H5. These are marked as d.
On combining these four fragments we can assign the following structure to the compound :

Hd
d

Hd
c
CH2

H
dH

Hd

b
a
CH CH3
a
CH3

SOLVED PROBLEMS BASED ON UV, IR, PMR AND ANALYTICAL DATA

Problem 1. An organic compound contain 666% carbon, 111% hydrogen and the rest
being oxygen. In its UV spectrum, it showed a characteristic band at 274 nm ( 17). In the IR
spectrum, it showed bands at 2941 - 2827 (m), 1715 (s) and 1460 (m) cm1. The PMR spectrum of
the compound exhibits three signals at -248, quartet (2H), 212, singlet (3H) and 107 triplet
(3H). Determine the structure of the compound.

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