SECTION A
1. la) (ii Which nwlccule can follow clectrophilic
substitution



1,5-cyclooctadiene is treated with I-Cl.
What is the structure of the product 12

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-1a1.jpg">

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-1b1.jpg"> is exposed to u v light and compounds C and D are produced. What
are the structures of C and D
1,3-butadienc is treated with S02. What product will be formed "

I Acetaldehyde is treated with excess formaldehyde in presence of Ba(0H)2 and the reaction produces a solid organic compound. What the structure of solid organic compound
12

Which one of these two compounds
<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-1c2.jpg"> has aromaticity 12
When compound A is treated with alkali what product is formed Show the mechanism of the conversion.

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-1d1.jpg">

What is the structure of the compound
produced from B on exposure with u v light?

B Ar CH C Ar

Ar 0
Ar 2,4,6-trimethyl phenyl


Isobutylene after reaction with H2S04 at
80°C, is hydrogenated using Ni-catalyst.
Write the structure of final product and
mechanism of its formation . .
12
12

Camphene hydrochloride on heating in
polar solvent produces isobornyl
chloride Write the mechanism of the
conversion.

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-1e2.jpg">

2. Phthalimide is treated with alcoholic KOH and it
produces a product A. A is treated with n-butyl
bromide producing B. The product B is boiled with
excess NaOH producing a volatile liquid C. After
removal of the solution on acidification gives a
solid organic acid D. What are C and Write
with equations.
Give st ructures of compounds and in
the following reactions

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-2b.jpg">

12
20
20


B(beta)-methyl crotonaldehyde <img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-2c.jpg"> on refluxing with dilute NaOH produces a product of chemical formula
C10H14O. What is the structure of the product? Write mechanism of the formation. 20
3. Show the most likely steps in the above transformation 15x4=60

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-3a.jpg">

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-3b.jpg">

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-3b.jpg">

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-3d.jpg">

4. Optically active exo-norbornyl tosylate produces racemic products of exo-norbornyl acetate in presence of KOAc in HOAc. Explain the mechanism of conversion.
<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-4a.jpg">

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-4b.jpg"> as a minor
product in acid medium. What is the mechanism of
conversion

Dihydropentalene (C8H8) is treated with two moles
of n-butyl lithium and it produces a white crystalline compound A. NMR spectrum of A is as follows
a doublet 8 4·98 J 3 Hz
b triplet 8 5·73 J 3 Hz
and peak ratio of a b 2 1. What is the structure of 20
20
20




5.
SECTION B
Tropolonc <img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-5a.jpg"> has following characteristics:
Has high dipole moment (3·71 D).
Follows Reimer Tiemann reaction.
Couples with diazonium ions.
Follows nitration with dilute HN03

What class of compounds does tropolone resemble Is it stable in acid or basic medium Explain. 12

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-5b.jpg"> on heating produces trans 9,10-Dihydronaphthalcne. What is the mechanism of this transformation

B(beta)-Lactone <img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-5b2.jpg"> can be obtained by
treatment of sodium maleate with Br2-water.
Explain the mechanism of its formation. 12

i Draw the rough-sketch of NMR spectra of
CH2Br CHBr2.
Which bond has higher frequency in IR
spectra

C N
C C

1,4-butadiene carrying alkyl or aryl substitution on can photochemically
rearrange to vinyl cyclopropane.

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-5d1.jpg">

Explain the transformati on.

What are the structures of pyrimidine
nucleotides present in DNA What are the
structures of their purine conjugates 12

e i The rate of rearrangement of
hydroazobenzene to benzidine is proportional
to square of concentration of in solution.
Explain.

Explain the mechanism of thermally allowed
concerted reaction between cis-1,3-butadiene
with ethylene using HOMO and LUMO. 12

6. A or B when treated with KN(C2H5)2 in diethyl
amine, it produces only C9H11N. What is the
product Write mechanism of its formation.

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-6a.jpg"> 15

Treatment of CH2 CH CN with NH3 p roduces
NH2 CH2 CH2 CN and
NH CH2 CH2 CN)2. Write mechanism of formation of these compounds. 15

How can adiponitrile C (CH2)4 CN) be produced from acrylonitrile 8
Write the mechanism of formation of

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-6c.jpg"> bishenol.

What are the products produced when
phenyl acetate is heated with AlC13 Write
the mechanism of formation. 8

What is the structural difference between
Nylon-6 and Nylon 6,6 What are the raw
materials of their synthesis

7 Resorcinol <img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-7a.jpg"> is
heated with NaHC03 under pressure. What will be the product after acidification
Which has higher stretching frequency in IR spectra? Explain.

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-7a.jpg">

On treatment with aqueous HBr, both cis and trans
2-bromocyclohexanol are converted into the same
product. What is the product Explain with mechanism of conversion.

15
15
15

What are the reagents B and used for the
following conversion 5x3=15

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-7a.jpg">

8. Write down the product of the above reaction
with chemical equation 5x3=15
<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-81a.jpg">
<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-8a2.jpg">
<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-8a3.jpg">

Identify tbe product of the following reaction with
mechanism

<img src="E:anuradhaCIVILS 2012CIVILS MAIN 2012images190-8b.jpg">

lndene C9H8 rapidly decolourizcs Br2/CC14. Only
one mole of H2 is absorbed readily to form C9H10.
Vigorous oxidation of indene produces phthalic
acid. What is the structure of indene If indene is
heated with strong acid, what product is formed 15
What arc the reagents used to distinguish the
following pairs 5x3??I5

r Primary alcohol (C2H50H) and tertiary
alcohol alcohol)
Cyc1ohexane and 1-Cyclohexenc
1-hexyne and 1-hexene