IIT JAM Chemistry Test Paper

1
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)
Q.1 to Q.10: Carry 1 Mark each.

1. The major product (P) formed will be
CH3
O O
OH
R O (P)
CH3 CH3 CH3

CH3
O
O O
COOH
O
O COOH
(a) (b) (c) (d)
O
2. Which of the following is most reactive as a nucleophile

(a) PhO  (b) PhS (c) Ph  CH 2  O  
(d) Ph  CH 2  NH 2
3. Which compound is the major product of the following reaction

Cl Cl MeOH
+ NaI Product
(a) Cl I (b) I Cl (c) I I (d) Cl OMe
4. Which ketone has the largest equilibrium constant for hydration
O O O
(a) (b) (c) (d)

O
5. Decreasing order of heat of hydrogenation in the following Alkenes.
(1) (2) (3) (4)
(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
3
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
(A) (B) (C)

O
(a) 3, 2, 3 (b) 2, 2, 3 (c) 3, 4, 2 (d) 2, 4, 3
9. The major product formed in the following reaction

Ph NMe2
LiAlH4, –AlCl3 (3 : 1)
(P)
Et2O
O
(a) Ph H (b) Ph OH
O
(c) Ph NMe2 (d) Ph NMe2
10. The reaction given below is an example of

MeO NO2 NO2
NaOEt
(a) E2-elimination (b) E1-elimination

(c) syn-elimination (d) E1CB-elimination
Q.11 to Q.30: Carry 2 Marks each.
11. Order of basicity in following compound will be
H NH2
H H
N
N N
(1) (2) (3) (4)
(a) 1 > 2 > 3 > 4 (b) 4 > 3 > 2 > 1 (c) 4 > 3 > 1 > 2 (d) 2 > 1 > 4 > 3
4
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
5
CH2I2, Zn-Cu
Product
16. Et2O
OH
The major product formed will be
(a) (b) (c) (d)

OH O OH O
I
Bu3SnH, AIBN
17. (P)
Ph-H, 80ºC
The major product formed in the above reaction is

O O
O
CH3
(a) (b) C11H23 (c) (d) none of these
18. The major product (P) is

OMe
+ 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
OMe OMe OMe OMe
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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
(a) (b) (c) * (d)
*
* *

(i) Me2NH/H+/HCHO
(P)
(ii) Me–I
N (iii) Hydrolysis
H
NMe2
(a) NMe2 (b)

N
H N
H
OH
(c) OH (d)
N N
H H
(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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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
28. Consider the following statements for [18]-annulene

(A) It is aromatic
(B) The inner protons resonate at  9.28 in its 1H NMR spectrum
(C) There are six protons in the shielded zone.
(a) A, B, C (b) A and B only (c) B and C only (d) A and C only
29. Among the structures given below, the most stable conformation for the following compound is
(a) (b) (c) (d)
30. The gauche conformation    60º  of n-butane posseses
(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)
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.
9
34. In which the product is formed through dis-rotation
H
 
(a) (b)
 
(c) (d)
35. The correct structure of the D-glucose is/are
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
36. Which of the following equation shown as correct product

O
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
37. The products formed in the following reaction is/are

(i) NaCN/HCN
D-ribose (P)
(ii) H2/Pd/BaSO4
(iii) H3O+
(a) D-Allose (b) D-Altrose (c) D-Glucose (d) D-Mannose
38. The correct statement(s) about the Diels-Alder reaction is/are
(a) electron donating groups on diene increases, the rate of Diels-Alder reaction
(b) electron donating groups on Dienophile decreases, the rate of Diels-Alder reaction
(c) Anthracene gives Diels-Alder reaction while as benzene does not give
(d) Aromatic character is directly proportional to the reactivity of Diels-Alder reactions
10
39. The number of compounds which under goes [3, 3] sigmatropic shift
(a) (b) (c) (d)
40. The correct statement(s) about the given compounds

(A) Ar CO2Me (B) Ar CO2Me (C) Ar CO2Me (D) Ar CO2Me
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
(1) (2) (3) (4)
(5) (6)
44. How many in the following molecules are chiral
H H H H
(A) HOOC (B) C C C (C) C C C
HOOC C6H5 H C6H5
HOOC
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp.ClMetro GateBrNo. 3), Delhi-09, Ph: 011-65462244, 65662255
H CH3
(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
How many product will be formed in above reaction.

52. How many compounds gives cannizaro reaction
O O
(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+
How many intermediate (carbocations) will be form in above conversion.

54. How many products will be formed on ozonolysis of following compound
12
CH3
Ozonolysis
(P)
CH3
55. C
Et O
C
Cl
H NH2
C
O O
Number of moles of CH3MgBr required to neutrals above compound is/are________________

56. Among the following neutral amino acids is/are
(1) Lyscine (2) Arginine (3) Valine (4) Aspartic acid
(5) isoleucine (6) Traphtophane (7) Leucine
57. The []D of a 90% optically pure 2-arylpropanoic acid solution is +135º. On treatment with a base at RT for
one hour, []D changed to +120º. The optical purity is reduced to 40% after 3 hours. If so, its specific rotation
after 3 hours would be ________________degree.
58. Among the following, how many are aromatic in nature?
O
N
(A) (B) N (C) (D)

S
O O
O
H
(E) (F) (G) (H)

N
O
(I) H H (J)
59. For the below compound
The  max value is ________ mµ.
13
NO2
H
EtO N
60. C
OH
O O O
In the above structure, how many functional groups are reduced by LiAlH4.
***** END OF QUESTION PAPER *****
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14
Space for Rough Work
15
IIT-JAM CHEMISTRY-CY
Date : 08-01-2017
TEST SERIES - 2 Booklet : B
(Organic Chemistry)
ANSWER KEY
Section-A : Multiple Choice Questions (MCQ)
1. (b) 2. (b) 3. (a) 4. (a) 5. (c)

6. (d) 7. (b) 8. (b) 9. (c) 10. (d)
11. (c) 12. (c) 13. (b) 14. (c) 15. (c)
16. (c) 17. (a) 18. (a) 19. (a) 20. (c)
21. (c) 22. (a) 23. (b) 24. (a) 25. (a)
26. (d) 27. (a) 28. (d) 29. (c) 30. (b)
Section-B : Multiple Select Questions (MSQ)
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)
Section-C : Numerical Answer Type (NAT)
41. (3) 42. (2) 43. (2) 44. (1)

45. (1755 to 1765) 46. (4) 47. (4) 48. (2)
49. (3.05) 50. (2) 51. (1) 52. (5)
53. (3) 54. (5) 55. (7) 56. (4)
57. (60) 58. (3) 59. (252) 60. (5)

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Q.1 to Q.10: Carry 1 Mark each.

CH3 CH3 CH3

2. Which of the following is most reactive as a nucleophile

3. Which compound is the major product of the following reaction

4. Which ketone has the largest equilibrium constant for hydration

(a) (b) (c) (d)

5. Decreasing order of heat of hydrogenation in the following Alkenes.

(1) (2) (3) (4)

(A) (B) (C)

9. The major product formed in the following reaction

10. The reaction given below is an example of

(a) E2-elimination (b) E1-elimination

(1) (2) (3) (4)

The major product formed will be

(a) (b) (c) (d)

The major product formed in the above reaction is

(a) (b) C11H23 (c) (d) none of these

18. The major product (P) is

OMe OMe OMe OMe

(a) (b) (c) * (d)

20. The product (P) is

(a) NMe2 (b)

28. Consider the following statements for [18]-annulene

(a) (b) (c) (d)

30. The gauche conformation    60º  of n-butane posseses

35. The correct structure of the D-glucose is/are

36. Which of the following equation shown as correct product

37. The products formed in the following reaction is/are

(a) (b) (c) (d)

40. The correct statement(s) about the given compounds

(1) (2) (3) (4)

44. How many in the following molecules are chiral

(A) HOOC (B) C C C (C) C C C

HOOC C6H5 H C6H5

Q.51 to Q.60: Carry 2 Marks each.

How many product will be formed in above reaction.

How many intermediate (carbocations) will be form in above conversion.

Number of moles of CH3MgBr required to neutrals above compound is/are________________

(A) (B) N (C) (D)

(E) (F) (G) (H)

59. For the below compound

The  max value is ________ mµ.

***** END OF QUESTION PAPER *****

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Section-A : Multiple Choice Questions (MCQ)

1. (b) 2. (b) 3. (a) 4. (a) 5. (c)

Section-B : Multiple Select Questions (MSQ)

Section-C : Numerical Answer Type (NAT)

41. (3) 42. (2) 43. (2) 44. (1)

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* END OF QUESTION PAPER *