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1
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
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33-35, Mall Road, G.T.B. Nagar,Opp. G.T.B. Nagar Metro Station Gate No. 3, Delhi-110 009
28-A/11, Jia Sarai, Near IITMetro Station, Gate No. 3, New Delhi-110 016
2
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
PART – A1. What should come in place of question mark ?
2 6 4 ?1 2 3 12
(a) 16 (b) 20 (c) 12 (d) 15
2. Count the total number of triangles in the figure :
(a) 25 (b) 28 (c) 32 (d) 30
3. Find unit digit : (48269)4403 – (26528)202
(a) 6 (b) 5 (c) 8 (d) 4
4. What is 12th term of a arithmetic progression if 3rd term is 6 and 9th term is 18.(a) 24 (b) 20 (c) 30 (d) 28
5. Pointing to a photograph of a man Rishika said, “He is the brother of the daughter of the wife of my husband”.How is the man related to Rishika ?(a) Cousin (b) Brother (c) Son (d) Uncle
6. Kamlesh moved a distance of 50 feet towards north from his starting point. He then turned to left side andcontinued to walk for 25 feet more, again he turned left and walked 40 metres. Finally he turned to his right. Inwhich direction is he facing now ?(a) West (b) East (c) North (d) South
7. A bacteria in a pot doubles itself in a day, if the number of bacteria in first day was 2, and in second day was 4and so on and the pot was completely filled in 30th day, then when was the pot half filled.(a) 15 days (b) 20 days (c) 29 days (d) 25 days
8. What is a equivalent single discount if a successive discount of 30%, 20% and 25% is given to a customer.(a) 55% (b) 58% (c) 70% (d) 68%
9. If height of a equilateral triangle is 4 3 cm, then what is the area of the triangle in square centimeter?
(a) 12 3 (b) 16 3 (c) 18 (d) 15 3
10. A train crosses a pole in 15 seconds and a platform of 125 m in 20 seconds. What is the length of the train?(a) 375 m (b) 400 m (c) 300 m (d) 350 m
PART – B11. The correct order of acidity of the circled hydrogens in the following compounds is
(I)
O
CH2Ph
H
(II)
O
NHPh
H
(III)
O
NPh
H
OH(IV)
O
OPh
H
(a) IV > II > III > I (b) IV > III > II > I (c) III > IV > I > II (d) III > IV > II > I
3
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
12. The IUPAC name of the given compound is
H3C CH3
OH
O
(a) 9, 9-dimethyltricyclo[4.2.1] non-3-ene-3-carboxylic acid(b) 9, 9-dimethylbicyclo[4.2.1] non-3-ene-3-carboxylic acid(c) 9, 9-dimethylbicyclo[1.2.4] non-1-ene-1-carboxylic acid(d) 9, 9-dimethylbicyclo[2.1.4] non-3-ene-3-carboxylic acid
13. Give the major product (P)
HO
HBr (P)
(a) Br
(b)
Br
(c)
Br
(d) Br
14. The major product in the given reaction isO
Br
H
t-BuOKt-BuOH/25ºC
(P)
(a)
O
H
(b)
O
(c)
O
(d)
O
4
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
15. The major product (P) is
O
O
CO2H(i) DPPA, Et3NBenzene, reflux(ii) C6H5CH2–OH (P)
(a) O
O
HN C OBn
O
(b) O
O
HN C OPh
O
(c)
O
O
O
O Bn(d)
O
O
NH Boc
16. Which among the following disaccharides has 1, 4 glycosidic linkage and upon acid hydrolysis givestwo different monosaccharides(a) Maltose (b) Lactose (c) Cellobiose (d) Sucrose
17. Among the following structures of an -amino acid s which one will exist at pH = 10
(a) H3NO
O
HHN
NH
H2N
(b)
HN
NH2
H2N
H3NO
O
(c)
HN
NH2
H2N
H2N CO2
H
(d)
HN
NH2
H2N
H3N
H
OH
O
18. Among the following, identify the achiral molecule
(a)
HOOC H
HCOOH
(b)
NR
HH3C
(c) S
O
C2H5 CH3
(d)
COOH
Br
19. The major product formed in the following reaction is
O(i) MeMgBr, CeCl3
(ii) PCC, CH2Cl2(P)
5
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South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
(a)
OH
(b)
OH
(c)
O
(d)
O
20. The compound ‘X’ can be obtained by diazotization (NaNO2 + HCl)CHO
(X)
(a)
OH
NH2
(b)
OH
NH2
(c)
OH
NH2
OH
NH2
and
(d)
OH
NH2
OH
NH2
andBy both
21.Ph
Me
O
H Et-MgBr (P)
The major product (P) in the above synthetic transformation is
(a) Ph
Me
OH
(b) Ph
Me
OH
(c) Ph
Me
OH
(d) Ph
Me
22. Which among the following pair can’t be distinguish on the basis of the melting point
(a)
OH
OH
and
OH
OH
(b)
OH
and
OH
6
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
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(c) HOOCCOOH and
HOOC COOH
(d) O
Ar CO2Me
andO
Ar CO2Me
23. In the given molecule,Ph
The base fragment (m/z) in mass spectrometry is(a) 92 (b) 91 (c) 162 (d) 77
24. AB7 is a pentagonal bipyramidal molecule (IA = ½ NA 100% and IB = ½ NA 100%). What will be the correctappearance for NMR signal of A
(a) (b)
(c) (d)
25. The correct order of carbonyl stretching frequencies in the IR-spectrum of following compounds (I-III),are(I) Ethylbutyrate (II) Vinyl acetate (III) Methyl benzoate(a) I > II > III (b) III > II > I (c) II > I > III (d) II > III > I
26. The major product (P) is
NO
CO2Et
N3 OH (i) NOCl/Py–25ºC
(ii) hv, benzeneN2 atmosphere
(P)
(a) NO
CO2Et
N3 ONO
(b) NO
CO2Et
H2NOH
(c) NO
CO2Et
N3 OH
N OH (d) NO
N3
O
CO2Me
27. The major product (P) is
R
SiMe2
OMe
DCM, –78ºC
Br
CHO
(P)
7
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(a)
SiMe2
OMe
R
CHO
Br(b)
SiMe2
OMe
R
Br
CHO
(c)
SiMe2
OMe
R
CHO
Br(d)
SiMe2
OMe
Br
CHO
R
28. The major product (P) is
N
Si iPr3
(i) Cu(NO3)2, Ac2O(ii) Bu4NF
(P)
(a) N
Si iPr3
NO2 (b) N
H
NO2 (c) N
H
NO2
(d) N
Si iPr3
NO2
29. The major product (P) isOTBS
TBSO
(i) Et4N+Cl3–
DCM/0ºC(ii) CH3C(OMe)3TsOH, 170ºC, 5d
(P)
(a)
Cl
CO2MeCl
TBSO
(b)
Cl
CO2MeCl
TBSO
(c) Cl
TBSO
Cl
CO2Me (d) CO2MeCl
TBSO
Cl
8
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
30. The number of aromatic compound among following will be
(1)
NC CN
(2) (3) N
N
(4) (5)
(a) 5 (b) 4 (c) 3 (d) 2
PART – C31. A tetrapeptide (A) contains amino-acids Phe, Val, Lys, Leu. In tetrapeptide (A) aromatic side chain is
present in N-terminal amino acid. Treatment of tetrapeptide (A) with Edmann reagent would give
(a)
HN
NS O
Ph
NH2
(b) HN
NS O
Ph
Ph
(c)
HN
NS O
Ph
(d)
HN
NS O
Ph32. The pair from the followings with correct order of its property indicated is
(a) O
O
>O
O
(Basic)
(b) >
(Dehydration)
OH OH
(c) >
(Acidic)
OH
HO O O
(d)
O
>
(Ionisation)
O ClCl
33. Among the following compounds, the compound having anti-conformation as a most stable conformation(a) HO
OH (b) HOF (c) F F (d) Br
Br
34. The correct order of solvolysis of the following pairs I, II and III, IV is
OPNB(I)
OPNB(II)
CNOTs
OTs
CN
(III) (IV)
and
(a) I > II and III > IV (b) I > II and IV > III(c) II > I and III > IV (d) II > I and IV > III
9
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
35. The major product (P) is
TBSO
Me
O
SO2Ph
HN N
Toluene/65ºC(P)
(a)
TBSO
Me
HO
SO2Ph
N N(b)
TBSO
Me SO2Ph
OHNN
(c)
TBSO
Me SO2Ph
HO
NN
(d)
TBSO
Me SO2Ph
HO
NN
36. The major products (A) and (B) in the given reaction sequence are
Cl F
CN
(i) ClSO3H(ii) NH3
(A) SH2N(B)
(a)
Cl F
CN
A =
H2NO2S
ClHN
CN
B =
H2NO2S
S
(b) Cl F
CN
A =
H2NO2S
NH F
CNH2NO2S
B =
S
10
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(c)
Cl F
CN
A =ClO2S
Cl F
CNO2S
B =
NH
S
(d)
Cl F
CN
A =
ClHN
CN
B =S
SO2NH2 SO2NH2
37. The major product (P) in the following reaction isO
Br2aqueous medium (P)
(a)
OHO
Br
(b)
OBr
Br
(c)
OBr
OH
(d)
O
Br38. The major product (P) is
F F
COOEtMe3Si
NLi
(1 equiv.)(P)
(a)
F
COOEtMe3Si
N
(b)
COOEtMe3Si
FN
11
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South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
(c)
F
Me3Si
F
O
N (d)
F
Me3Si
F
N
39.
CF3
CCl2••
(X)
OMe
CCl2••
(Y)
(a)
Cl2C
CF3
and CCl2
OMe
(b) CCl2
CF3
and
Cl2C
OMe
(c)
Cl2C
CF3
and
Cl2C
OMe
(d) CCl2
CF3
and CCl2
OMe
12
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
40. The major product (P) is
O
O O
NH P
O
(OPh)2O
O
PhI(OAc)2I2, DCM
r.t. W-Lamp
(P)
(a)
O
O O
NH2O
O
(b)
O
O O
NH2O
H
(c)
O
HO OH
N
P(OPh)2O
O
O (d) O
N
PO
O
O
(OPh)2
O O
41. The product (P) formed in the following reaction sequence is
L-proline(i) BnOCOCl/Base
(ii) LiAlH4/Et2O(iii) work up
(iv)
O
/H+
(v) H2, Pd/C
(P)
(a) N
Cbz
O (THP)(b) N
Cbz
OH
(c) N
H
O(THP) (d) N
(THP)
O Cbz
13
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
42. The major product A + B formed in the following reaction sequence are
OHOH
TBDMS-Cl, DMSO (A)Li, NH3, t-amylalcohol
THF, –40ºC(B)
(a) OHOTBDMS
A =OHOTBDMS
B =
(b) OHOTBDMS
A =OHOTBDMS
B =
(c) OTBDMSOH
A =OTBDMSOH
B =
(d) OTBDMSOH
A =OTBDMSOH
B =
43. The major products A and B formed in the following reaction are
(A) H2, Pd/C
OH
CO2H H2, Rh-Al2O3 (B)
(a) A =
OH
B =
OH
OH
(b) CO2H
A =CO2H
B =
OH
(c) CO2H
A =CO2H
B =
(d) A =CO2H
B =
OH
OH
14
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
44. The major products (A) and (B) formed in the following reaction sequence aret-BuOOH, Ti(OiPr)4
(+)-DIPT, –20ºC(B)
Ph NNHTs
O (i) EtMgBr(ii) H2O
(A)
(a) A =Ph
OH
B =Ph
OH
O
(b) A =Ph
OH
B =Ph
OH
O
(c) A =Ph
OH
B =Ph
OH
O
(d) A =Ph
OH
B =Ph
OH
O45. Addition of Br2 to (Z)-2-butene gives
(a) (2R, 3R) dibromobutane through achiral brominium ion(b) (2S, 3S) dibromobutane through achiral brominium ion(c) Mixture of (2R, 3R) and (2S, 3S) dibromobutane through chiral brominium ion.(d) Mixture of (2R, 3R) and (2S, 3S) dibromobutane through achiral brominium ion.
46. Which of the following pair having homotopic ligand
(a)
COOH
Hb OH
COOH
HO Ha
and
COOH
Ha OH
COOH
Hb OH (b) H3C
Ha
CH3
Hband
H3C
H
Ha
Hb
(c) •Cl
HHb
Ha
and •Cl
H•
Hb
Ha
(d) Ha
Hb
H
Cl
Cl
H and
HHa
OH
HHb
OH
47.
CH3
H(A)
H
CH3
(B)
The correct statement regarding structure (A) and (B) is(a) (A) is more stable over (B) (b) (B) is more stable over (A)(c) Both (A) and (B) are having same energy (d) Conformational flipping is possible in both (A) and (B)
48. The major product (P) and the steps involved the following reaction sequence are
O
CO2Me
+O
(i) MeOK, THF(ii) K2CO3, MeOH
reflux (P)
15
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South Delhi : 28-A/11, Jia Sarai, Near-IIT Metro Station, New Delhi-16, Ph : 011-26851008, 26861009
(a) O
P =
CO2Me
, Michael addition followed by intramolecular Aldol and dehydration
(b) O
P =
CO2Me
, intramolecular Aldol followed by Michael addition and dehydration
(c) P =
CO2Me
O
, Michael addition followed by intramolecular Aldol and dehydration
(d) P =
CO2Me
O
, intramolecular Aldol, followed by Michael addition and dehydration.
49. Consider the following statements(A) Base pairing will be never possible between two purine or two pyrimdine bases(B) Sugar containing hemiacetal can undergo mutarotation(C) All amino acid reacts in the same manner with nitrous acid(D) Majority of terpenoids belongs to animal kingdomThe incorrect statement among the following are(a) A and D only (b) A and C only (c) A, C and D only (d) C and D only
50. The major product (P) and the reaction involved in the following reaction is
NH
BnCHO (P)
NH2
(a) NH
NH
BnP = , mannich reaction
(b) N
P =
NBn
, mannich reaction
(c) NH
P =
N
Bn, Aza-cope rearrangement
16
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(d) NH
P =
NH
Bn , Aza-cope rearrangement
51. The major product (P), is
S
+
OO O
(i) AlCl3, r.t.(ii) Zn/Hg, aq. HCl(iii) SOCl2/(iv) AlCl3/
(P)
(a) S
O
Cl
O
(b) S
O
(c)
S
O
(d)
S
O
O
52. The major product (P) is
O SnBu3
NBoc
(i) n-BuLi (1.1 eq.) THF
–78ºC to r.t. 12h(ii) H2O
(P)
(a)
OH
NBoc
(b)
O
NBoc
OH
(c) N
Boc
OH (d) N
Boc
OH
17
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53. The major product (P) isOH
(i) K2CO3, HBr
DMF
(ii)N3
CuSO4, sodium ascorbatet-BuOH
(P)
(a)
NN
N
OPh
(b)
NN
NPhO
(c)
NN
N
Bn
PhO (d)
NN
N
Bn
BnO
54. The major product (P) is
O
OBn
BnO
OBn
(i) Cl3CCOCl
Zn-Cu, Et2O, 0ºC(ii) m-CPBANaHCO3/DCM
(P)
(a)
O
OBn
BnO
OBn
O
Cl
Cl•• (b)
O
OBn
BnO
OBn
•• O
Cl Cl
O
(c)
O
OBn
BnO
OBn
••
O
Cl Cl
O
(d)
O
OBn
BnO
OBn
•
O
Cl Cl
O
18
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55. In a NMR spectrometer containing a 4.5T magnet. The Larmor precession frequency of 1H is 500MHz . The radio frequency used in this spectrometer has an associated magnetic field strength of5×10–6 T. The duration of a 90º pulse in this instrument is(a) 2.5×10–4 sec (b) 25×10–6 sec (c) 4.5×10–5 sec (d) 9.5×10–6 sec
56. The number of 13C NMR signals exhibited by the compounds (A-C), are, respectively
(A) (B)
OH
H
OHH
OH
OH
H
H
OH
HO
(C)
O
(a) 4, 5, 5 (b) 4, 6, 6 (c) 2, 5, 7 (d) 2, 6, 7
57. A compound having molecular formula C11H12O exhibits following spectral data:
1IR ,v cm : 1706, 1600
Mass (m/z) : 160, 145 (base peak)1H NMR , ppm : 7.3–7.8(m, 4H); 1.5 (s, 6H), 2.6 (2H, s)The singlet at 2.6 ppm is exchangeable after prolonged treatment with D2O containing a trace of DCl.
(a) O (b)
O
(c)
O
(d) O
58. Aromatic compounds among (I to V) are
O
S
O
(I) (II) (III) (IV) (V)(a) I, III and IV (b) I, II and IV (c) III and IV (d) III, IV and V
19
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59. The product (P) in the following reaction is
Nicotine (i) Alk. KMnO4(ii) SOCl2(iii) NH3(iv) KOH/Br2
(P)
(a) 2-amino-Py (b) 3-Amino-Py(c) 2-amino-nicotinamide (d) 3-amino-nicotinic acid
60.
OHH
SbF5(P)
OHH (i) Bu4NCH3CO2
DMF(Q);
(ii) NaOH, H2O
SOClF
Which of the following statement is true regarding above reaction.(a) P = Q = optically active R-2-butanol(b) P = Q = racemic mixture of 2-butanol(c) P = racemic mixture of 2-butanol whereas Q is optically active R-2-butanol(d) P = optically active R-2-butanol whereas Q = racemic mixture of 2-butanol
20
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Space for rough work
21
North Delhi : 33-35, Mall Road, G.T.B. Nagar (Opp. Metro Gate No. 3), Delhi-09, Ph: 011-27653355, 27654455
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CSIR-UGC-NET/JRF | GATE CHEMISTRY
CHEMICAL SCIENCESTEST SERIES-B (ORGANIC CHEMISTRY)
ANSWER KEY
PART-A1. (b) 2. (b) 3. (b) 4. (a) 5. (c) 6. (a) 7. (c)
8. (b) 9. (b) 10. (a)
PART-B
11. (b) 12. (b) 13. (b) 14. (d) 15. (a) 16. (b) 17. (c)
18. (d) 19. (c) 20. (d) 21. (b) 22. (d) 23. (a) 24. (b)
25. (c) 26. (c) 27. (b) 28. (c) 29. (a) 30. (c)
PART-C
31. (b) 32. (a) 33. (d) 34. (a) 35. (d) 36. (a) 37. (c)38. (a) 39. (a) 40. (d) 41. (c) 42. (d) 43. (b) 44. (c)45. (d) 46. (d) 47. (a) 48. (a) 49. (c) 50. (a) 51. (c)52. (c) 53. (c) 54. (b) 55. (c) 56. (d) 57. (b) 58. (d)59. (b) 60. (c)
Date : 21-11-2018
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