Question 1:

Molecular formula = C6H5OBr

Hydrogen bond deficiency index = C+1 –[H+X/2]

= 6+1- [5+1/2]
=4

Functional groups from IR:

Wavenumber cm-1 Functional group
3300 (broad) OH
1600 C=C
1230 C-O
840 Aromatic

H-NMR data:
Chemical shift Splitting Integration Interpretation
5.5 Broad singlet 1 OH
6.8 Doublet 2 2 equivalent CH groups having one
proton in neighbor
7.3 Doublet 2 2 equivalent CH groups having one
proton in neighbor

Structure:
Br OH

Mass Spectrum peak:

Molecular ion peak arise when molecule lose one electron and become free radical cation and M+2
peak is isotopic peak which arise due to heavier isotope of the bromine. And natural abundance of
bromine is 1:1 there for intensity of M+2 is 1:1 And base peak arise when CO is lost from a molecular
cation which was formed by loss of Br.
 e
Br OH Br OH

m/e 172

-Br

-CO
OH

m/e= 65 m/e =93

Question 2:

Molecular formula = C6H4ClNO2

Hydrogen bond deficiency index = C+1 –[H+X-N/2]

= 6+1- [4+1-1/2]
=5

Functional groups from IR:

Wavenumber cm-1 Functional group
1520 and 1350 NO2
1600 C=C
840 Aromatic

H-NMR data:
Chemical shift Splitting Integration Interpretation
7.3 Doublet 1 C-H having one proton in neighbor
8.1 Doublet 1 C-H having one proton in neighbor

Structure:
Cl NO2

Mass Spectrum peak:

Molecular ion peak m/z= 157 arise when molecule lose one electron and become free radical cation
and M+2 peak is isotopic peak m/z=159 which arise due to heavier isotope of the chlorine. And
natural abundance of Chlorine is 1:3 there for intensity of M+2 is 1:3
 e
Cl NO2 Cl NO2

m/z=157

-NO2

Cl

m/z=111