south delhi : 28-a/11, jia sarai, near-iit metro station, new … · is a pentagonal bipyramidal...

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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

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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

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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

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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)

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(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

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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


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


R

SiMe2

OMe

DCM, –78ºC

Br

CHO

(P)

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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


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

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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

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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

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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

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(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

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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

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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

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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)

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(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

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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


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

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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


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

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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

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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

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Space for rough work

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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

south delhi : 28-a/11, jia sarai, near-iit metro station, new … · is a pentagonal bipyramidal...

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