Exam Details
| Subject | chemistry | |
| Paper | paper 2 | |
| Exam / Course | indian forest service | |
| Department | ||
| Organization | union public service commission | |
| Position | ||
| Exam Date | 2015 | |
| City, State | central government, |
Question Paper
I.F.S. EXAM:·2015
C-GEQ-0-DINB
CHEMISTRY
Paper-II
ITime Allowed Three Hours I !Maximum Marh 200 I
QUESTION PAPER SPECIFIC INSTRUCTIONS
Please read each of the following instructions care/ ully before attempting questions
There are EIGHT questions in all, out of which FIVE are to be attempted.
Question Nos. 1 and 5 are compulsory. Out of the remaining SIX questions, THREE are ta be attempted
selecting at least ONE question from each of the two Sections A mid B.
Attempts of questions shall be counted in sequential order. Unless struck off. attempt of a question shall
be counted even if attempted partly. Any page or portion of the page left blank in the Question-cum-Answer
Booklet must be clearly struck off
All questions carry equal marks. The number of marks carried by a question/part is indicated against it.
Answers must be written in ENGLISH only.
Unless othenvise mentioned, symbols and notations have their usual standard meanings.
Assume suitable data, if necessary and indicate the same clearly.
Neat sketches may be drawn, wherever required.
SECTION-A
Q. 1. Answer the following 5X8=40
Q. Write the product of given reactions and explain which product is most stable. 5
0
0
Base
OcO
OcO
Base
Q. Aniline on treatment with sodium nitrite and HCl in cold gives a product which on
. I
treatment with J3-napthol gives Write the structures of and and name of the
reaction involved. 5
Q.
Write the mechanism of following electrocyclic reaction
5
H
Q.
Write the product and its stereochemistry for the reaction
CH 3Br
Draw
energy profile diagram and write a mechanism. If concentration of CHBr is -increased
3
4 times, what will be the effect on the rate of reaction
5
..
Q.
Write the product/s with their stereochemistry for the reaction of cyclohexene with
Br2
Br2
in NaCl
Br2
in CH30H 5
Q.
Write a mechanism for the reaction 5
OH
Sketch a mechanism for the following conversion 5
0
CH2Br
benzene
Q.
Cyclohexylmethyl ketone on treatment with peroxyacid in presence of CHCIgives
3
cyclohexyl acetate. Write a mechanism for the reaction.
5
1
Q. I Reaction of 3-butadiene with HBr at -80°C and 45°
C gives two regioisomeric allylic
halides in different ratios. Write the products in both the cases and indicate the major
product. Explain the reason for the influence of temperature on product distribution.
10
Q.
Write Zaitsev rule. Acid catalyzed dehydration of 1-methylcyclohexanol gives a mixture
of two isomeric alkenes. Write the products and indicate major product. 10
-....
Q.
Explain whether the reactions shown below will proceed by SN1 or SN2 mechanism.
Justify your answer. 10
.J
..:xOMc
HO
ccJ
Q.
Which of the following compounds will give same allylic carbocation on ionization
10A,J;
Cl y Cl
Cl
Cl
Cl
Q.
Write the product formed and its stereochemistry when
trans, trans-2,4-hexadiene reacts photochemically.
cis, trans-2,4-hexadiene reacts thermally.
10
Q.
Write a mechanism to show the photolytic ring closure of a-pyrone. Predict the stereocbemistry
of the product. l 0
Q.
Identify in the reaction
(C2H5)2
CHCONH2
Write the name of the reaction and a detailed mechanism to explain the formation of
1
10
1
1
Q. Using benzene as one of the reactants, how will you prepare the following using Friedal-
Crafts reaction
4-oxo-4-phenylbutanoic acid
Isobutylbenzene. 10
Q. 4. Identify fPJ to [WJ in the following and write the name of reaction involved
10X4=40
.. NH2 (C2H50)2CH(CH2)3NH2
..NH/
t
10
ii) ..
Pp5
ii) Pd-C
CH3COCI
10
CHCl/NaOH
ii) w
CH}2 ..
10
NaOH
SECTION-B
Q. Answer the following
Sx8=40
Q.
Dacron is a polyester. It is obtained from 4-benzenedicarboxylic acid and 2-ethanediol.
Write its structure. 5
Q.
Write the name and draw the structures for two purines and three pyrimidines that occur
in RNA and/or DNA. 5
Q.
In 1HNMR spectrum of a compound at 200 MHz, a signal at 1058 Hz was observed.
Calculate the chemical shift for this proton. 5
·
Q.
Consider
4-pentadienc, 2-methyl-1,3-butadiene and cyclopentene.
Explain which of these will exhibit A max to longer wavelength and why 5
Q. What do you understand by 'base peak' in mass spectrum Which of the following
compounds will exhibit a base peak at m/z 105 5
HF2i.H3 i5tH2C
H3C
CHH3C
CH3
3
Q.
Identify in the reaction ·
OH
(CH3)3 COOH
0
a
0504
t-butyl alcohol/Off
OH
and comment on the nature of syn/anti-hydroxylation of cyclohexene.
5
Q. A compound on treatment with LiAlH4
· gives an equal number of moles of 1-butanol and 2-propanol. Identify 5
Q.
Suggest a structure for the product of following reaction 5HC
B2H
6
ii) HP2, Of
H
f
CH3
1
and 7.3
Q. Explain what type of information is provided by the following spectroscopic techniques
UV
I
I
I
IR
1 HNMR
Mass and
esr or epr Justify your answer with suitable example. 10
Q. Consider m-and p-dichlorobenzenes. Write how many signals in 1 HNMR spectrum of these compounds you are likely to get. Justify your answer. 10
tox3=30
:rite ]ism of fo..:wing reac;..
Q.
s
I
fi
10
N
N
Norrish type
I 0
hv
10
CH2
I
.. n
(CH)CH
10
22
Hz
An organic compound having molecular formula C7H6Cl30 exhibited m/z at 212.53. HNMR spectrum of the compound exhibited signals at o 3.9 6.8 (d)Write the possible structure for the compound with suitable justification.
I j
I I
I
.
CH= CH2
(Cl12).
5
t
Q. Write the product of following reactions
..
..
hv
hv
10
Q. Calculate Mn and Mw for a polymer prepared by mixing equal number of molecules of I molar mass 10,000 and 1 ,00,000. I 0
Q. How will you detennine the relative viscosity and specific viscosity of a polymer solution
using Ostwald viscometer I 0
Q. Write the monomers used in the preparation of following polymers
Polyisobutylene
Nylon 6
Teflon
Nylon 6
Polyvinylchloride. 10
Q. What is a peptide bond What is the difference between a peptide, .:,Jigopeptide and
protein What type of bonding is largely responsible i.. the secondary stru:ture of protein
IO
Q. Write the product of following reactions
..
..
hv
hv
10
Q. Calculate Mn and Mw for a polymer prepared by mixing equal number of molecules of I molar mass 10,000 and 1 ,00,000. I 0
Q. How will you detennine the relative viscosity and specific viscosity of a polymer solution
using Ostwald viscometer I 0
Q. Write the monomers used in the preparation of following polymers
Polyisobutylene
Nylon 6
Teflon
Nylon 6
Polyvinylchloride. 10
Q. What is a peptide bond What is the difference between a peptide, .:,Jigopeptide and
protein What type of bonding is largely responsible i.. the secondary stru:ture of protein
IO
C-GEQ-0-DINB
CHEMISTRY
Paper-II
ITime Allowed Three Hours I !Maximum Marh 200 I
QUESTION PAPER SPECIFIC INSTRUCTIONS
Please read each of the following instructions care/ ully before attempting questions
There are EIGHT questions in all, out of which FIVE are to be attempted.
Question Nos. 1 and 5 are compulsory. Out of the remaining SIX questions, THREE are ta be attempted
selecting at least ONE question from each of the two Sections A mid B.
Attempts of questions shall be counted in sequential order. Unless struck off. attempt of a question shall
be counted even if attempted partly. Any page or portion of the page left blank in the Question-cum-Answer
Booklet must be clearly struck off
All questions carry equal marks. The number of marks carried by a question/part is indicated against it.
Answers must be written in ENGLISH only.
Unless othenvise mentioned, symbols and notations have their usual standard meanings.
Assume suitable data, if necessary and indicate the same clearly.
Neat sketches may be drawn, wherever required.
SECTION-A
Q. 1. Answer the following 5X8=40
Q. Write the product of given reactions and explain which product is most stable. 5
0
0
Base
OcO
OcO
Base
Q. Aniline on treatment with sodium nitrite and HCl in cold gives a product which on
. I
treatment with J3-napthol gives Write the structures of and and name of the
reaction involved. 5
Q.
Write the mechanism of following electrocyclic reaction
5
H
Q.
Write the product and its stereochemistry for the reaction
CH 3Br
Draw
energy profile diagram and write a mechanism. If concentration of CHBr is -increased
3
4 times, what will be the effect on the rate of reaction
5
..
Q.
Write the product/s with their stereochemistry for the reaction of cyclohexene with
Br2
Br2
in NaCl
Br2
in CH30H 5
Q.
Write a mechanism for the reaction 5
OH
Sketch a mechanism for the following conversion 5
0
CH2Br
benzene
Q.
Cyclohexylmethyl ketone on treatment with peroxyacid in presence of CHCIgives
3
cyclohexyl acetate. Write a mechanism for the reaction.
5
1
Q. I Reaction of 3-butadiene with HBr at -80°C and 45°
C gives two regioisomeric allylic
halides in different ratios. Write the products in both the cases and indicate the major
product. Explain the reason for the influence of temperature on product distribution.
10
Q.
Write Zaitsev rule. Acid catalyzed dehydration of 1-methylcyclohexanol gives a mixture
of two isomeric alkenes. Write the products and indicate major product. 10
-....
Q.
Explain whether the reactions shown below will proceed by SN1 or SN2 mechanism.
Justify your answer. 10
.J
..:xOMc
HO
ccJ
Q.
Which of the following compounds will give same allylic carbocation on ionization
10A,J;
Cl y Cl
Cl
Cl
Cl
Q.
Write the product formed and its stereochemistry when
trans, trans-2,4-hexadiene reacts photochemically.
cis, trans-2,4-hexadiene reacts thermally.
10
Q.
Write a mechanism to show the photolytic ring closure of a-pyrone. Predict the stereocbemistry
of the product. l 0
Q.
Identify in the reaction
(C2H5)2
CHCONH2
Write the name of the reaction and a detailed mechanism to explain the formation of
1
10
1
1
Q. Using benzene as one of the reactants, how will you prepare the following using Friedal-
Crafts reaction
4-oxo-4-phenylbutanoic acid
Isobutylbenzene. 10
Q. 4. Identify fPJ to [WJ in the following and write the name of reaction involved
10X4=40
.. NH2 (C2H50)2CH(CH2)3NH2
..NH/
t
10
ii) ..
Pp5
ii) Pd-C
CH3COCI
10
CHCl/NaOH
ii) w
CH}2 ..
10
NaOH
SECTION-B
Q. Answer the following
Sx8=40
Q.
Dacron is a polyester. It is obtained from 4-benzenedicarboxylic acid and 2-ethanediol.
Write its structure. 5
Q.
Write the name and draw the structures for two purines and three pyrimidines that occur
in RNA and/or DNA. 5
Q.
In 1HNMR spectrum of a compound at 200 MHz, a signal at 1058 Hz was observed.
Calculate the chemical shift for this proton. 5
·
Q.
Consider
4-pentadienc, 2-methyl-1,3-butadiene and cyclopentene.
Explain which of these will exhibit A max to longer wavelength and why 5
Q. What do you understand by 'base peak' in mass spectrum Which of the following
compounds will exhibit a base peak at m/z 105 5
HF2i.H3 i5tH2C
H3C
CHH3C
CH3
3
Q.
Identify in the reaction ·
OH
(CH3)3 COOH
0
a
0504
t-butyl alcohol/Off
OH
and comment on the nature of syn/anti-hydroxylation of cyclohexene.
5
Q. A compound on treatment with LiAlH4
· gives an equal number of moles of 1-butanol and 2-propanol. Identify 5
Q.
Suggest a structure for the product of following reaction 5HC
B2H
6
ii) HP2, Of
H
f
CH3
1
and 7.3
Q. Explain what type of information is provided by the following spectroscopic techniques
UV
I
I
I
IR
1 HNMR
Mass and
esr or epr Justify your answer with suitable example. 10
Q. Consider m-and p-dichlorobenzenes. Write how many signals in 1 HNMR spectrum of these compounds you are likely to get. Justify your answer. 10
tox3=30
:rite ]ism of fo..:wing reac;..
Q.
s
I
fi
10
N
N
Norrish type
I 0
hv
10
CH2
I
.. n
(CH)CH
10
22
Hz
An organic compound having molecular formula C7H6Cl30 exhibited m/z at 212.53. HNMR spectrum of the compound exhibited signals at o 3.9 6.8 (d)Write the possible structure for the compound with suitable justification.
I j
I I
I
.
CH= CH2
(Cl12).
5
t
Q. Write the product of following reactions
..
..
hv
hv
10
Q. Calculate Mn and Mw for a polymer prepared by mixing equal number of molecules of I molar mass 10,000 and 1 ,00,000. I 0
Q. How will you detennine the relative viscosity and specific viscosity of a polymer solution
using Ostwald viscometer I 0
Q. Write the monomers used in the preparation of following polymers
Polyisobutylene
Nylon 6
Teflon
Nylon 6
Polyvinylchloride. 10
Q. What is a peptide bond What is the difference between a peptide, .:,Jigopeptide and
protein What type of bonding is largely responsible i.. the secondary stru:ture of protein
IO
Q. Write the product of following reactions
..
..
hv
hv
10
Q. Calculate Mn and Mw for a polymer prepared by mixing equal number of molecules of I molar mass 10,000 and 1 ,00,000. I 0
Q. How will you detennine the relative viscosity and specific viscosity of a polymer solution
using Ostwald viscometer I 0
Q. Write the monomers used in the preparation of following polymers
Polyisobutylene
Nylon 6
Teflon
Nylon 6
Polyvinylchloride. 10
Q. What is a peptide bond What is the difference between a peptide, .:,Jigopeptide and
protein What type of bonding is largely responsible i.. the secondary stru:ture of protein
IO