CHEMISTRY
Paper-11
(Time Allowed: Three Hours) (Maximum Marks 200)
INSTRUCTIONS
Candidates should attempt Question Nos. 1 and 5 which ar:e compulsory. ·and any of the remaining questions, selecting at least ONE question from egch Section. All questions carry equal marks. Marks for each part/sub-part of a question are indicated against each. Answers must be written in ENGLISH only. Assume suitable data, if considered necessary, and indicate the same clearly. Unless otherwise indicated, symbols and notations have their usual meanings. Important Note All parts/sub-parts of a question must be answered contiguously. That is, where a question is being aitempted, all its constituent parts/sub-parts must be attempted before moving on to the next question. Pages left blank, .if any, in the answer-book(s) must be clearly struck out. Answers that follow pages left blank may not be given. credit.

SECTION-A
Which of the foliowing compounds are aromatic
or non-aromatic G1ve reason. 5x2
·1 r

II N"

.
What is a carbene and how is it formed How
can you distinguish between the two types of
carbenes by a chemical method Show by a
reaction, choosing an appropriate example .
.5+5
How does the following affect SNl and SN2
reaction ,Explain by "one example in
each. case. 2x5
Structure of alkyl halide
2
II
·(Contd.)
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Relative reactivity of halogen
Nucleophile
Solvent
Rearrangement.
How can you distinguish between E1 anq E2
reaction on the basis of kinetic isotope effect
10
2. What is a pericyclic reaction Explain thermal
addition of butadiene with ethylene showing
molecular orbitals. 10
What happens when p-cresol reacts with
chloroform in presence of NaOH Explain the
formation of products with mechanism. 10
Complete the reaction with mechanism. 10
A B

Acid catalyzed dehydration of neopentyl alcohol
yields 2-methyl-2-butene as the major product.
Outline a mechanism showing all steps of
formation. 10
3
D
(Contd.)
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... -....... 1":"1!11" .. -· ..... .. ·.- ••
3. Write mechanistic steps involved in the Diekmann
reaction. I 0
Give the products, mechanism for their formation
and name the reaction

HN,
NH,
Phenylhydrazine
Aldehyde
or Ketone
10

Glycerol+ Aniline B
h PhNO,
l 10
Give the product. Explain its formation and nonformation
of the other by giving mechanism
and rea5oning. 10
4
II
Base

(Contd.)
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Give the product and give mechanism for the
(orm-ation ·of product 5
0
I. LiAIH,
. . 2. H20
A
0
..
Write the mechanistic steps involved m the
formation of the given product I 0
0
I. MeLi
2. dil. so,
3. a,o
Butenone, on addition ofHCN gives two different
products. On the basis of the mechanism involved,
draw an energy profile diagram showing formation
of both kinetic and thermodynamic product. Also,
predict the more stable product. I 0
Identify A-D and give mechanism for their
0
formation. • I 0
NH,NH, OW

5
II

B
ow H•
C

(Contd.)
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Identify the in the following reaction,
What is the intermediate involved 5
hv
R-CH -CH -CH -CH 2 2 2 2 l EtOH
SECTION-8
5. Give the formation of nylon 6 and nylon 6
with the help of chemical reaction. 10
Describe the light scattering method for
determination of weight average molecular weight
of polymers. 10
Show the mechanistic steps for·the free .radical
formation of polystyrene. Show the formation of
Styrene-acrylonitrile co-polymer. 10
What are phosphorazines Draw the structures
of the following phosphonitrilic chlorides
(NPC12

3
(NPC1 2

4
6 •
10
{Contd.)
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6. Predict the products .of .the following reactions
showing suitably stereochemistry wherever
necessary; 5 x 5

L.i/L.iq. NH3
t-BuOH
OCH3
NBS
CH-COOH 0 0
II ·
......::..
4

CH-COOH


0
0
OH
OH


HI04
•





Show the mechanistic steps for the formation of
products by the reaction of0s04 and cis-2 butene.
Indicate and comment upon the stereochemistry
of the final products. I 0+5
7 (Contd.)
D
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7. Outline the suitable mechanism for the following





Ph
transfonnations 4x5=20
Ph
0

Ph
Ph
Ph
Ph
8 •
hv
hv
hv
hv
Ph
Ph
en
Ph
j
Ph
Ph 0 I
Ph
I
Ph
Ph
(Contd.)
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Predict the structures of D and E
10
I Pb (OAc)4
AcpHiReflux

Write down the possible electronic transitions as
applied to fluorescence arid phosphorescence.
5
The low resolution NMR spectrum of a compound
having molecular formula C4 H4 0 2 shows two
peaks of equal intensity. Draw the structure.
5
8. Answer the following·
Reaction of an organic compound with a
mixture of cone. H
2
S04 and cone. HN03 gave
two isomeric compounds major and minor.
The compound exhibited the following spectral
characteristics
Molecular formula C7 H7N03
IR: 3040, 1610, 1510, 1350 and 1030 cm-1
9
II
(Contd.)
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1H-NMR: o 8.1 J 8
6.8 J 8 Hz) and
3.9
Deduce the structure of and with:
proper explanation. 15
Explain typical fragmentations for the mass
spectrum of 1-phenylethanol. 5
Explain, how the UV-vis spectrum can be used
to distinguish the following isomeric compounds.
5


An organic compound with molecular formula
C
3
H
7
NO gives absorption peaks in the regions
3413 3030-2899 1667 1634 and
1460 cm-1 in IR spectrum. Give its probable
structure.
10
Ill
5
(Contd.)
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Amines absorb at higher wavelength as compared
to alcohols, why 5
Which of the following system will show ESR
spectrum
H
N
2
cu+
CH
3
r
II
a
Na+
NO
cu+2
C0
2 5
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