Multiple choice questions: 09x1=09M

1. How would the proton indicated would appear in the 1H NMR spectrum of the compound
given below:

a) Singlet

b) doublet

c) triplet

d)quartet

2. How many different types of protons are observed in 1H NMR of isobutanol:

a) 4

b) 5

c) 3

d) 2

3. Which functional group is responsible for the broad, strong peak at 3354 cm-1:
a) carboxylic acid
b) amine
c) alcohol
d) phenol
4. Which of the following spectroscopic technique is of best choice to differentiate the given
compounds :

a) IR b) UV c) 13C NMR d) none

5. In IR spectral analysis of C=O and C=C bonds.Which one of the following is true:
a) the stretching frequency of C=O is greater than C=C
b) the stretching frequency of C=C is greater than C=C
c) the stretching frequencies are same but C=O shows more intense absorption
d) the stretching frequencies of C=C and C=O are same but C=C shows more intense absorption

6. The increasing order of stretching frequency of the following compounds:

a)
b)
c)
d)

7. In mass spectrum, the base peak is:

a) the tallest peak b) highest m/z value c) the smallest peak d) none
8. The characteristic of a compound containing bromine atom is:
a) the heights of M and M+2 are equal

b) the heights of M and M+1 are equal

c) the height of M and M+3 are equal

d) none

9. The decreasing order of stretching frequency of carbonyls is:

Section-II
Answer the following questions: 6x2=12M

1.
undergoes Mclafferty rearrangement readily. As a results strong peak is observed
at m/z=58. Write mechanism for this cleavage using appropriate arrows and give the structure of
the fragment responsible for this peak.
2. If the force constants for C-Cl and C-O are same, which one of these occurs at a larger
wavenumber. Justify your answer
3. In IR spectra, O-H bond will show more intense absorption than N-H bond. Explain.

4. The chemical shift of OH proton of an alcohol ranges from 2 to 5 ppm, whereas the OH proton
of carboxylic acid ranges from 10 to 12 ppm. Explain.
5. Identify whether the compound is isopropyl alcohol or isopropylamine from the IR spectra,
given below. Justify your answer.

6. Identify the compound from the given 1H NMR spectrum

Section-III
Answer the following questions: 3x3=9M
1. How many different peaks would you expect to find in the 1H-NMR spectrum of each of the
compounds
a) propane

b)propene

c) ethyl methyl ether

2. Explain, how would you distinguish 2, 2-dimethyl butane and 2, 3-dimethyl butane using mass
spectroscopy. Structures are given below

3. Mass, IR and 1H & 13C NMR spectra of a compound are given. Identify the compound

Elemental Analysis: C, 23.55; H, 3.29; Br, 52.23; O, 20.92