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IIT JAM Chemistry Test Paper
IIT JAM Chemistry Test Paper
2. Section-A contains 30 Multiple Choice Questions (MCQ). Each question has 4 choices (a), (b), (c) and (d),
for its answer, out of which ONLY ONE is correct. From Q.1 to Q.10 carries 1 Marks and Q.11 to Q.30
carries 2 Marks each.
3. Section-B contains 10 Multiple Select Questions(MSQ). Each question has 4 choices (a), (b), (c) and (d)
for its answer, out of which ONE or MORE than ONE is/are correct. For each correct answer you will be
awarded 2 marks.
4. Section-C contains 20 Numerical Answer Type (NAT) questions. From Q.41 to Q.50 carries 1 Mark each
and Q.51 to Q.60 carries 2 Marks each. For each NAT type question, the value of answer in between 0 to
9.
5. In all sections, questions not attempted will result in zero mark. In Section–A (MCQ), wrong answer will
result in negative marks. For all 1 mark questions, 1/3 marks will be deducted for each wrong answer. For
all 2 marks questions, 2/3 marks will be deducted for each wrong answer. In Section–B (MSQ),there is no
negative and no partial marking provision. There is no negative marking in Section –C (NAT) as well.
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Section-A : Multiple Choice Questions (MCQ)
O O
OH
R O (P)
O O O
(a) 1 > 2 > 3 > 4 (b) 4 > 3 > 2 > 1 (c) 4 > 2 > 1 > 3 (d) 2 > 3 > 4 > 1
6. The incorrect statement(s) about the furan is/are
(a) Furan gives electrophilic substitution reaction faster than benzene
(b) Furan is less aromatic then benzene
(c) Furan gives poly bromination with Br2 in non-alcoholic solvents.
(d) Furan does not gives Diels-Alder reaction
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7. The major product (P) is
MeS
(i) (Boc)2/Base
OH (P)
H2N (ii) NaHCO3/Bn-Cl
(iii) H+
O
MeS MeS
OBn OBn
(a) (Boc)HN (b) H2N
O O
MeS MeS
OH OH
(c) H2N (d) (Boc)HN
O O
8. How many signals would you expect in the 13C NMR of the following compounds , respectively
O
O
(c) Ph NMe2 (d) Ph NMe2
NaOEt
(a) 1 > 2 > 3 > 4 (b) 4 > 3 > 2 > 1 (c) 4 > 3 > 1 > 2 (d) 2 > 1 > 4 > 3
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NH (i) NaNH2
12. (ii) MeOTs
Product will be ?
(iii) LDA
(iv) EtBr
O O O O
Me
NH2
N N
(a) (b) (c) (d)
13. Which is the major product of the following reaction of an acyl azide?
O
Ph
N3
(i) Toluene,
(P)
(ii) H2O
O O O
Ph NH2
NH2 Ph H
OH Ph
(a) (b) (c) (d)
14. Which combination of compounds in a-d identifies A and B in the following reaction
OMe
Na, Liq. NH3 HCl, H2O
(A) (B)
EtOH, Et2O
OMe O OMe O
, , B=
(a) A = B= (b) A =
OMe O OMe O
(c) A = , B= (d) A = , B=
15. Which is obtained as the main product upon reaction of m–t-butylanisole (1-t-butyl-3-methoxybenzene) with
conc. (HNO3 + H2SO4)
O2N NO2
(a) (b) (c) (d)
OCH3
OCH3 O2N OCH3 OCH3
NO2
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CH2I2, Zn-Cu
Product
16. Et2O
OH
I
Bu3SnH, AIBN
17. (P)
Ph-H, 80ºC
O
CH3
+ Me Me
(P)
O
OMe
OMe O OMe O OMe O OMe O
C C C C
Me Me Me Me
(a) (b) (c) (d)
Me Me Me Me
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19. The product (P) is
*
O
R2 R1
(P)
OH
OH OH
OH
R2 R1
R2 R1 R2 R1
R2 R1
*
* *
OH
(c) OH (d)
N N
H H
21. The product (P) is
(i) BuLi
(P)
(ii) (Boc)2O
N (iii) EtO2C C C CO2Et /
H
EtO2C C C N C
(a) C N Boc (b) C
H Boc C
CO
O 2 Et
Boc Boc
N N
EtO2C
CO2Et CO2Et
(c) (d)
EtO2C
CO2Et CO2Et
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22. The product (P) is
OH
O (i) MeOH/HCl
HO (P)
HO (ii) MeCHO/p-TSA
OH OH
OH
Me O O
O O
O O
(a) HO (b) Me
OH
OH OMe
OMe
Me
(c) Me O (d)
O
O OMe O
O
HO O OMe
HO
OH
OH
23. Suggests structure for the products of these reactions, interpreting the spectroscopic data
MeO
Br (P)
MeOH
O
Molecular formula : C6H12O2
max cm 1 1745 ; C ppm :179, 52, 39, 27 ; H ppm ,1.20 9H, s , 3.67 3H,s
O
O Me OMe O
Me H
(a) (b) O (c) (d)
O O O
24. The configuration at the two stereocentres in the compound given below are
Me
O
1
4
H
(a) 1R, 4R (b) 1R, 4S (c) 1S, 4R (d) 1S, 4S
25. Among the carbocations given below
H
H
(A) (B) (C)
(a) A is homoaromatic, B is antiaromatic and C is aromatic.
(b) A is aromatic, B is antiaromatic and C is homoaromatic.
(c) A is antiaromatic, B is aromatic and C is harmoaromatic.
(d) A is homoaromatic, B is aromatic and C is antiaromatic.
26. The order of carbonyl stretching frequency in the IR spectra of ketone, amide and anhydride is:
(a) Anhydride > amide > ketone (b) Ketone > amide > anhydride
(c) Amide > anhydride > ketone (d) Anhydride > ketone > amide
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27. In the 1H NMR spectrum recorded at 293 K, an organic compound (C3H7NO), exhibited signals at 7.8
(1H, s), 2.8 (3H, s) and 2.6 (3H, s). The compound is
O O
H NH
(a) H NMe2 (b) Me (c) Me (d)
N NMe2 N Me
H Me OMe
(a) plane of symmmetry; and is achiral (b) C2-axis of symmetry; and is chiral
(c) centre of symmetry; and is achiral (d) plane of symmetry; and is chiral
Section-B : Multiple Select Questions (MSQ)
Q.31 to Q.40: Carry 2 Marks each.
31. Select the compounds undergoing inter or intra molecular Cannizaro reaction
O H O
O
Cl
(a) Ph (b) (c) (d) OHC CH2 OH
Br Ph CHO
Cl H O
32. In which reactions benzyne will be formed as intermediate
F NH2
(i) HNO2
(a) + Mg (b) (ii)
Br COOH
N
F
N NaNH2
(c) (d)
S
O
O
33. The incorrect statement(s) about the heterocyclic compounds is/are
(a) Pyrrole gives electrophilic substitution reaction while as pyridine give nucleophilic substitution reactions
(b) Pyrrole does not act as basic while as pyridine does.
(c) Furan and thiophine gives electrophilic substitution reactions with equal rate
(d) Pyrrole gives nucleophilic addition reaction with Grignard reagent.
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34. In which the product is formed through dis-rotation
H
(a) (b)
(c) (d)
OH OH CHO
O OH OH H OH
O OH
HO H
O
OH
(a) (b) (c) HOHO (d) H OH
HO OH H OH
OH OH
OH
OH OH CH2OH
NH2
NH2
(a) Br2, NaOH
H2O
N N
CH2N2
(b) COCl CH2 COOH
H2O
O O
CF3COOOH
(c) H3C C C(CH3)3 (H3C)3C O CH2 CH3
H2
NaN3
(d) COCl NH2 + CO2
H2O
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39. The number of compounds which under goes [3, 3] sigmatropic shift
O O O O
(a) A and B are enantiomers (b) B and D are diastereomers
(c) B and C are homomers (d) C and D are enantiomers
Section-C : Numerical Answer Type (NAT)
Q.41 to Q.50: Carry 1 Mark each.
41. Among the following, how many incorrect statement for the following reaction is/are _________
1. MeMgBr, Et2O
+
2. H3PO4
(A) (B)
(1) A is the major product and it will have five signals in the proton decoupled 13C NMR spectrum
(2) A is the minor product and it will have eight signals in the proton decoupled 13C NMR spectrum
(3) B is the major product and it will have five signals in the proton decoupled 13C NMR spectrum
(4) B is the minor product and it will have five signals in the proton decoupled 13C NMR spectrum
42. Nucleophilic substitution reactions of pyridine occurs at which position ____________
43. The number of compounds which undergoes Diels-Alder reaction
(5) (6)
H H H H
HOOC
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H CH3
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(D) CH3 (E)
Cl
11
C N O
C
48. HOOC Cl
NO2
In the above structure, how many functional groups not reduce by borane.
49. Calculate the pI of the following salt of amino acid having pKa value x = 2.2, y = 3.9 and z = 7.9 respectively.
HO
O
OH
H3N
O
50. How many products will be formed upon the bromination of furan in alcoholic and non-alcoholic solvent.
CH3
H+
+ (P)
51.
OCH3
(1) Cl3 C CHO (2) Cl3C C CCl3 (3) OHC CHO (4) Cl3C C CH2 CCl3
C(CH3)3
(5) O (6) N (7)
H O
O O
53. Reaction,
OH
H+
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CH3
Ozonolysis
(P)
CH3
55. C
Et O
C
Cl
H NH2
C
O O
(I) H H (J)
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NO2
H
EtO N
60. C
OH
O O O
In the above structure, how many functional groups are reduced by LiAlH4.
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Space for Rough Work
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IIT-JAM CHEMISTRY-CY
Date : 08-01-2017
TEST SERIES - 2 Booklet : B
(Organic Chemistry)
ANSWER KEY
31. (a),(b), (c) 32. (a),(b), (c) 33. (c),(d) 34. (b), (c)
35. (a),(b),(c), (d) 36. (a), (b), (d) 37. (a),(b) 38. (a),(b), (c)
39. (a), (c), (d) 40. (a), (b), (d)
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