ORGANIC CHEMISTRY

TARGET JEE-ADVANCE
IRP

JUMBO HOME
TEST

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 VIBRANT ACADEMY ORGANIC CHEMISTRY
IRP Jumbo Test
(India) Private Limited Target IIT ADVANCE-2020

Single Correct Choice Type :

1. In the following reaction, if the concentration of HOCH2CH3 is tripled, what will happen to the rate of the
reaction?

Cl EtOH OEt

(A) Triple (B) Decrease by a factor of 3

(C) Increase by a factor of 6 (D) No change in rate
(E) Increase by a factor of 9
2. What reagents would be required to perform the following reaction ?

D
O 
OH
(A) NaBH4, CH3OD (B) NaBH4, CH3OH (C) NaBD4, CH3OD (D) NaBD4, CH3OH
(E) LiAlD4, CH3OH
3. Predict the major product of the following reaction.

OH
PBr3

Br
Br PBr2
(A) (B) (C) (D)

OPBr2
(E)

4. What is the major product of the following reaction ?

OH
LDA
I

OH
N
(A) N (B)
I

(C) (D) O

(E) O

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 +
H3O Conc. H 2SO 4 O 3/H 2O/Zn
5. O + CH3MgBr A B C

A, B and C are :

HO CH3 CH3 CH3 HO CH3 CH3 O

O
(A) CHO (B) , HCHO

HO CH3 CH3 CH3 HO CH3 CH3 O

CHO O
(C) (D) CHO
CHO

Na/NH3 C C H2
6. B A
Lindlar catalyst

A and B are :

(A) in both case (B) in both case

(II)
(I)
(C) A is I, B is II (D) A is II, B is I
7. The compound that does not react with NaHCO3 and NaOH as well
(A) Carbolic acid (B) Benzyl alcohol (C) Butyric acid (D) Pcric acid
8. What is the major product of the following reaction ?
1. Br2
2. NaNH 2 (3 eq)
3. H 2O

Br Br

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

Br
Br

Br

(E)
NH2
9. Predict the product of the following reaction.
1. HgSO4, H2SO4, H2O
Hexyne
2. LiAlH4
3. H2O

O
(A) (B) (C) (D)
OH Li O H

(E)
OH

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10. Predict the product of the following reaction
H
2 equiv. HBr

Br
Br Br Br Br
(A) (B) (C) (D)
Br
Br

Br
(E) Br

11. I dentify the reagent from the following list which can easily distinguish between 1-butyne and 2-butyne
(A) Br2, CCl4 (B) Ammonical AgNO3 (C) H+/HgSO4 (D) H2/Pd-BaSO4

12. The compound having most basic nitrogen is :

NH2
CONH2
(A) (B) (C) (D)
N N

13. Approximate value of KH/KD when PhCHBrCH3 v/s PhCDBrCD3 is allowed to react with t-butoxide :
(A) = 1 (B) < 1 (C) > 1 (D)  0

14. What is the product of the following reaction ?

(1) H3PO4, heat,

(2) O2, heat
+
(3) H3O , heat

O OH

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

15. What product(s) would you expect to obtain from the following reaction?

O
H
NaOCH3, CH3OH
H3C

H3C OCH3 H3C OH OH HO

H H H
(A) (B) (C) (D)
H3CO H3CO H2C H3C OCH3

H3CO
H
(E)
H3C OH

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16. Which of the following would not efficiently accomplish the reaction shown ?

OH O



(A) NaH (B) Na(metal) (C) –NH2 (D) K (metal)

(E) –OH

17. Most acidic phenol derivative is :

OH OH OH OH

NO2 CH3
(A) (B) (C) (D)

NO2 CN

18. In the given following compound find out the pair of enantiomers and diastereomers respectively.
R – CH – CH – R
Cl Br
(A) 2, 2 (B) 2, 4 (C) 4, 4 (D) 4, 2

19. Hyperconjugation involves overlap of the following orbitals

(A)  –  (B)  – p (C) p – p (D)  – 

20. Which of the following compound is inert toward E2 reaction.

Br
CH3 CH3
| |
(A) CH3 – CH – CH2 – CH3 (B) (C) CH3 — C — CH2 — Br (D) CH3 — C — CH — CH3
| | | |
Br CH3 CH3 Br
OH

21.

Best method for above reaction is :

(A) conc. HCl + ZnCl2 (B) conc. H3PO4
(C) HBr (D) conc. HCl
22. In the reaction :
Li –Liq NH3 Br2
Me – C  C – Me      (P),
CCl4

The principal organic product (P) is

(A) Meso-2, 3-dibromobutane
(B) Racemic mixture of (+) and (–) forms of 2,3-dibromobutane
(C) Racemic mixture of 2-amino-2,3-dibromobutane
(D) DIastereoisomeric mixture of 2-amino-2,3-dibromobutane.

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23. The major product of the following reaction is

Me Br
- +
F PhS Na
dimethylformamide

NO2

Me SPh Me SPh Me Br Me SPh

F F SPh SPh
(A) (B) (C) (D)

NO2 NO2 NO2 NO2

CH3
B2H6 H2O2
24. Product(s)
THF NaOH
(A) 2 optically active isomers (B) A meso compound
(C) 2 optically active & 1 meso compound (D) Optically inactive

O
||
25. Functional isomers of CH3 – C – OH are :

(A) 2 (B) 3 (C) 4 (D) 5

26. Acetamide is treated separately with the following regents. Which of these would give methylamine ?
(A) PCl5 (B) Sodalime (C) NaOH + Br2 (D) Hot, conc. H2SO4
27. Most reactive toward SN–Ar

F Cl Br I

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

NO2 NO2 NO2 NO2

28. The reagent which does not react with both, acetone and benzaldehyde.
(A) NaHSO3 (B) Phenyl hydrazene (C) Fehling solution (D) Grignard reagent

NH2
29. KOBr
(x)  

(x) will be
CONH2
CONH2 CONH2 CONH 2

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

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 NO2

(i) KOH, 
30. (A)
(ii) H3O+ Major product
Cl
F
(A) will be

NO2 NO2 NO2 OH

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

OH OH Cl Cl
OH F OH F

31. The major product of the following reaction is :

O
C
(i) KOH
NH
C (ii) Br CH2Cl
O

O O
C C
(A) N – CH2 Br (B) N CH2Cl
C C
O O

O O
C C
(C) N (D) N
C C
O – CH2 Br O CH2Cl

32. Predict the products of the following reaction.

O
HBr

OH OH
HO Br
(A) + (B) +

Br Br
HO Br
(C) + (D) +

Br
(E) +

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 Br
O  
|| conc . O Na
AlCl3 Br2 / Fe Zn(Hg) HNO3
33. + CH3 – C – Cl    (A)   (B)     (C)    (D) (E)
HCl 

Product (E) is

O
NO2
Br O2N

(A) (B) O (C) (D) None

Br O
Br
Br

dil KMnO 4 H IO 4 OH –
34. [X]      A    B   
O
Possible structure of [X] is
CH3

(A) (B) (C) H3C (D)

CH3 CH3 CH3 CH3

35. Which of the following polymer can be formed by using the following monomer unit ?
H
N O

(A) Nylon-6, 6 (B) Nylon-2, 6 (C) Nylon-6 (D) Melamine polymer

OH

36. Optically active stereoisomers of are :

OH
(A) 4 (B) 3 (C) 2 (D) 1

37. CH3CHO CH3MgBr (A) Conc.H2SO 4 (B) B2H 6,H2O 2 (C)

H 2O H2O
Relation between (A) and (C)
(A) Identical (B) Positional (C) Functional (D) Geometrical

38. Sucrose on hydrolysis yields a mixture which is :

(A) Optically inactive (B) Dextrorotatory (C) Laevorotatory (D) Racemic

OH

39. In the Cannizzaro reaction given below, 2Ph–CHO  Ph–CH2OH + PhCO 2 the slowest step is :
(A) the attack of OH– at the carbonyl group
(B) the transfer of hydride to the carbonyl group
(C) the abstraction of proton from the carboxylic acid
(D) the deprotonation of Ph–CH2OH

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40. How many D-aldopentoses are possible ?
CHO
H OH
H OH
a typical aldopentose
H OH
CH2OH
(A) 2 (B) 3 (C) 4 (D) 6
(E) 8
41. Which of the following might you expect to exhibit mutarotation?
HO HO
O OCH3 O OH
(A) HO OH (B) HO OH
OH HO
OH
O
HO
OH HO
OH
O O H HO
HO
O O
O OH H
(C) HO OH (D) (E)
H H H OH
HO CH2OH
H OH
OH H

CHO

(1) N2D4,OD,D2O
42. Final product is :
(2) HI
OMe
OH
CH3 CDO CD2H CD3

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

OMe OD OH OMe
OH OD OH OH
43. What is the major product of the following reaction?
O
OH
HO NH3, heat
O

O O O O

NH2 NH2 NH
(A) HO (B) H2N (C) NH (D)
O O O
O
44. Which of the following Alcohol will give positive iodoform test

(A) CH3OH (B) CH3–CH2–OH (C) CH3CH2CH2OH (D) OH

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45. What products would be formed in the reaction shown ?

CHO
H OH
HO H
H OH excess HIO4
H OH
CH2OH

CO2H CO2H
H OH H OH
HO H HO H CHO
H OH H OH
(A) (B) (C) 2 H OH
H OH H OH
CH2OH
CH2OH CO2H

O O O O
(D) 5 + (E) 3 + 2 + CO2
H OH H H H OH H H

46. The iso-electric point of the following -amino acid will lie at which pH if the following data are pKa1 = 2.2,
pKa2 = 9.0 and pKa3 = 10.4

H 3N (CH2)3 CH COOH
NH3

(A) 9.7 (B) 5.7 (C) 6.3 (D) 1.4

47. Which of these are anomers.

H OH HO H HO H
H OH H OH HO H
O O O
HO H HO H HO H
H OH H OH H OH
HO H
H H
CH2OH CH2OH CH2OH
(I) (II) (III)
(A) I and II (B) II and III (C) I and III (D) III is anomer of I and II

48. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product?

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

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49. Consider the following six compounds (A–F).

CH2OH
CHO CHO CHO C=O CH2OH
HO H HO H H OH H OH HO OH
H O OH HO
H OH H OH HO H H O
H OH H OH
H OH H OH HO H
H OH H HO OH
H OH HO H H OH OH
CH2OH CH2OH CH2OH CH2OH OH H

A B C D E F

Which relationship is wrong

(A) A and B-diastereomer (B) A and C-diastereomer
(C) B and C-Enantiomer (D) A and D-Functional (E) E and F-Anomer

50. Predict the major product of the following reaction.

OH 1. P + Br2
Ph
2. NH3, H2O
O

NH3 
 OH NH2  O
O Ph Ph
(A) Ph (B) (C) (D) H3N
NH O O
O
 NH2
H3N
(E)
O
51. Glucose and Fructose can be distinguished by :
(A) Ammoniacal AgNO3 (B) Fehling’s solution
(C) Bromine water (Br2 + H2O) (D) reaction with Ph – NH – NH2

CH3 CH3
52. (– CH2 – C – CH2 – C –)n
CH3 CH3
is a polymer having monomer units

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

53. The commercial name of polyacrylonitrile is

(A) Dacron (B) Orlon (C) PVC (D) Bakelite
54. The following carbohydrate is
OH
O
HO

OH
HO OH
CH3
(A) Aldohexose (B) Ketoheptose (C) -furanose (D) -pyranose

55. Monomer used to prepare Orlon is:

(A) CH2=CHCN (B) CH2=CH–Cl (C) CH2=CHF (D) CH2=CCl2

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56. Consider the carbohydrates below and choose the statement that is true.

CHO CHO CHO

H OH HO H H OH
H OH HO H HO H
H OH HO H H OH
HO H H OH HO H
CH2OH CH2OH CH2OH
(W) (X) (Y)

(A) W and X are enantiomers (B) W and Y are enantiomers

(C) W and X are diastereomers (D) W and Y are diastereomers
(E) Two of the above statements are true
57. Which of the following amino acids might you expect to find in proteins?
H2N H H NH2
(A) CO2H (B)
CO2H

CO2H
CO2H H NH2
CO2H
(C) (D) (E) H NH
H NH2
Me
58. Periodic acid splits glucose and fructose into formic acid and formaldehyde. Ratio of formic acid and
formaldehyde from glucose and fructose is :
(A) 5/1 and 4/2 (B) 5 / 1 and 5/1 (C) 4/2 and 4/2 (D) 5/1 and 3/2
59. How many amino acids are involved in the structure of met-enkephalin?

O O O
H H
N N
N N OH
H H
NH2 O O
HO
S
(A) Three (B) Four (C) Five (D) Six (E) Seven
60. Which of following is essential amino acid?
(A) Glycine (B) Alanine (C) Valine (D) Histidine

61. Number of different tripeptities possible from Glycine, alanine and phenylalanine are :
(A) 9 (B) 18 (C) 27 (D) 81

62. Identify the polymer having strongest intermolecular force of attraction

(A) Natural rubber (B) Nylon (C) Starch (D) Cellulose
63. The process shown below is known as the Hofmann Elimination. What will be the major product?
NH2 1. excess CH 3I
2. Ag2O, heat

CH3
H3C CH3 H3C CH3
N N
(A) (B) (C) (D)

(E)

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64. The three xylenes (dimethyl benzene) do not undergo electrophilic aromatic substitution at the same rate.
CH3 CH 3

Cl2 CH3 Cl2

; rate r1 ; rate r2
AlCl3 AlCl3
CH3
CH3

Cl2
; rate r3 The correct order of relative rate r1, r2, r3 is :
AlCl3
CH3
(A) r1 = 200 ; r2 = 2, r3 = 1 (B) r1 = 1 ; r2 = 2, r3 = 200
(C) r1 = 2 ; r2 = 200 ; r3 = 1 (D) r1 = 2 ; r1 = 1 ; r3 = 200

CH3

CH3Cl AlCl3
65. (A ) (B)
AlCl3, 25ºC 100ºC
(major ) (major )
CH3

Intermediate product A and final product (B) are respectively.

CH3 CH3 CH3

CH3 CH3 CH3

(A) , (B) ,
CH3 CH3
CH3 CH3

CH3 CH3 CH3

CH3
CH3 H3C CH3
(C) , (D) ,
H3C CH3 H3C CH3
CH3

66. Total number of different cross aldol condensation product (only structural) obtained when a mixture of (S) 2-
methyl cyclohexanone and 2-butanone is treated with aqueous sodium hydroxide :

O
O
NaOH
+ ??
H2O

(A) 2 (B) 3 (C) 4 (D) 5

67. Which of the following pairs can be separated by resolution.

Br Br
OH OH HO OH
(A) (B)
Br Br

CH3 CH3
HO H H OH Br
(C) H OH HO H (D)
Br
CH3 CH3
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68. Total number of stereoisomers theoritically possible for the compound shown below
OH
O

O
HO
(A) 5 (B) 8 (C) 10 (D) 16

Light
69. + N Br or peroxide
(Product)

Final product is :

Br
Br
(A) (B) (C) (D)
Br

pH = 11.8
70. + MnO4– (A) + (B)
(ppt.)

Me Me Me OH
H OH H OH HO H H Me
(A) HO H (B) H OH (C) H OH (D) H OH
Me Me Me Me

71. Isoprene + HCl  (conjugate addition product is) :

Cl
(A) (B) (C) (D) Cl
Cl
Cl

200ºC O3
72. + H2C = CH2 C7H10 (B)
CH3–S–CH3
(A)
Final product (A) and (B) are respectively ?

OHC CHO
OHC CHO
(A) , (B)

CHO
OHC CHO
(C) , CHO (D) ,

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73. Find product of the reaction below :

HO OH
BF3

O O O O

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

74. Treatment of a sulfade with 1 mol of 30% aqueous hydrogen peroxide at room temperature gives (A).
Treatment of (A) with a second mole of hydrogen peroxide brings about its oxidation to (B).

H 2O 2 H2O2
S CH3 (P) (Q)
25ºC 25ºC
Identify products (P) and (Q) ?

O
O O
|| ||
(A) P = S – CH3 ; Q = S – CH3 (B) P = OH ; Q =
||
O
O O
||
(C) P = SO3H ; Q = OH (D) P = S – CH3 ; Q = S – CH3

75. Moles of AlCl3 consumed in Friedel Craft alkylation and acylation are respectively :
(A) 0.1, 1.1 mole (B) 0.1, 0.1 mole (C) 1.1, 1.1 mole (D) 1.1, 0.1 mole

CF3I
76. CH3–CH2–CH2–CH = CH2 (A)
light
Major product (A) is

I
(A) CH3CH2CH–CH2–CH2F (B) CH3–CH2–CH2–CH–CH2
I CF3
CF3
(C) CH3CH2CH2CH–CH2 (D) CH3CH2–CH–CH2–CH2–I
CF3 I

HBr (A)
without peroxide
77. CH=CH2
HBr (B)
Peroxide
Final products (A) and (B) are
Br
(A) Product A : ; Product B : CH2–CH2–Br

(B) Product A : ; Product B : CH2–CH2–Br

Br

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 Br
(C) Product A : ; Product B : CH–CH3
Br
Br
(D) Product A : CH2–CH2–Br ; Product B :

78. Total number of products including stereoisomers that are formed when (R)-3-methyl-1-pentene is treated
with following :
CH3

CH3 – CH2 – CH – CH = CH2 

(R)
(1) Hg(OAc)2, H2O followed by NaBH4 (2) H2/Pt
(3) BH3 following by H2O2 in NaOH (4) Br2/CCl4
(A) 6 (B) 5 (C) 8 (D) 11
79. How many diastereomeric pair formed when R-4-methyl cyclohexene react with OsO4 ?
(A) 1 (B) 2 (C) 3 (D) 4

80. E Product Reactants

(A)
Product (B)

Given the following energy diagram for a hypothetical reaction, which statements would be true of the reac-
tion ?
(A) Product B will be formed faster, but product A would predominate at equilibrium if both reactions are
reversible.
(B) Product A will be formed faster and product A would predominate at equilibrium if both reactions are
reversible.
(C) Product B will be formed faster and product B would predominate at equilibrium if both reactions are
reversible.
(D) Product A will be formed faster, but product B would predominate at equilibrium if both reactions are
reversible.

81. B2H6 H2O2 SOCl2 t-butOK (X)

THF OH
(W)
(W) & (X) are
(A) Positional isomers (B) Identical (C) Chain isomers (D) None
82. A compound which easily undergo Bromination, even in absence of Lewis Acid
(A) Phenol (B) Toluene (C) Benzene (D) Benzoic acid
12
83. Which statement is wrong for Ph C OOH
12 14 14
(A) Evolve C O2 in present of NaOH / CaO (B) Evolve C O 2 in present of NaH C O 3
(C) Red litmus change to blue (D) Fruity smell with C2H5OH / 
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84. Identify (A) is
Br
Br2 / H2O NaNO2  2HCl C2H5OH
( A )  (B)    (C)  

Br Br
OH
COOH OH NH2
COOH
(A) (B) (C) (D)

SO3H

85. Predict the major product of the following reaction.

O
1. KOH
NH
2. Br
O 3. H2NNH2
O O

 N
(A) N (B) N (C) H 2N (D) H N
2

O O

86. An interesting heterocycle is prepared by the reaction sequence shown below. Which one is it? Try to follow
each step, not just guess at the answer.

1. O3
2. Me2S
3. NH3
N
N N
(A) N (B) (C) (D)

O O
O HO
87. OCH3 OCH3

Above conversion can be achieved by

(A) LiAlH4 (B) NaBH4 (C) H3O+ (D) PCC
88. Give the major product of the following reaction :
O

O O
LiAlH4
O–CH3 H+ H
+

O O

(A) O (B) O

O
O
(C) O (D)
O

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89. Identify the relationship in products obtained in given reaction.

+ HCl  Product(s)

(A) enantiomers (B) diastereomers (C) identical (D) different

90. Which of the following compounds would you expect to react most rapidly with methanol to do the following
reaction ?
R – Br + CH3OH  R – O – CH3 + HBr

Br Br Br
(A) (B) Br
(C) (D)

91. 1-propanol & 2-propanol can be best distinguished by:

(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acidic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2SO4 followed by reaction with Fehling solution

92. Predict the product of the following reaction.

KMnO4, KOH, H2O, heat

O O O O
OH
(A) (B) (C) O (D) OH
OH
OH
O
O O

93. An organic compound C3H6O does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent and does
not react with metallic sodium. It could be:
(A) CH3CH2CHO (B) CH3COCH3 (C) CH2=CH–CH2OH (D)CH2=CH–O–CH3

94. The correct order of boiling point is :

O O
CH3 – CH2 – NH2 CH3 – C CH3 – CH2 – OH CH3 – C
(I) NH2 (III) OH
(II) (IV)

(A) IV > II > III > I (B) IV > II > I > III (C) II > IV > III > I (D) II > IV > I > III

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 O
(1) NaOI
 (B) 
KMnO 4
95. (A)   (C) + gas  

 Ph – C – OH + CHI3
(2 ) H
Structure of (A) is
OH OH O
(A) Ph – CH2 – CH – CH2 – OH (B) Ph – C – CH2 – C – H
CH3

OH OH OH
(C) Ph – CH – CH2 – CH2 – OH (D) Ph – CH – C – CH3

CH3

96. PhCH2CHO + CH3COCH3 dil.KOH (A)

Identify compound (A) which is give positive iodoform test.
O O
(A) Ph–CH2–CH=CH–C–CH3 (B) Ph–CH=CH–C–CH3

O
O
(C) Ph– CH2–CH=CH–C–H (D) CH3

Multiple Correct Choice Type :

97. Tautomerism is exhibited by :

O
O OH O

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

O
H

HBr
98. ?
CCl4

Product(s) can be

(A) Br (Major) (B) (Major)

Br

Br
(C) (Minor) (D) (Minor)
Br

99. Which of the following compound has one of the Stereoisomer as a meso compound ?

Cl Cl
Cl Cl
Cl
(A) (B) (C) (D)

Br Cl
Cl

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100. The correct statement(s) concerning the structures E, F and G is (are)

H3C O H3C OH H3C CH3

H3 C CH3 H3 C CH3 H3C OH

(E) (F) (G)

(A) E, F and G are resonance structures (B) E, F and E, G are tautomers

(C) F and G are geometrical isomers (D) F and G are diastereomers

101. Provide the reagents necessary to carry out the following conversion

CHO COOH
HO H HO H
H OH H OH
HO H HO H
CH2OH CH2OH

(A) Br2/H2O (B NaOH/H2O (C) HNO3 (D) Ag+/NH3/H2O

102. conc. HNO3 + H2SO4

Intermediates of this reaction is/are

NO2 NO2

  
(A) NO (B) NO (C) (D)
2

103. Which of following on acid catalysed hydrolysis give two product that give positive Iodoform test.

O
(A) O (B)

(C) O (D) H2C = CH — O – C = CH2

|
CH3
104. CH3Br + NaSH (excess)  Identify
all possible product

O
(A) CH3SH (B) CH3SCH3 (C) CH3–CH3 (D) CH3 – S – C – CH3

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105. Which of the following reactions give explosive compounds.
CH3

Conc. HNO3 + Conc. H2SO4

(A) Compound


OH

Conc. HNO3
(B) Compound


CH2 – OH
Conc. HNO3 + Conc. H2SO4
(C) CH – OH Compound

CH2 – OH

O
|| 1. NaOH / 5–10ºC
(D) H – C – H + CH3 – CHO Compound
excess 2. Conc.HNO3 +
conc.H2SO4, 
106. In which of the given reaction cumene is the product.
OH
+
,H , H3PO4
(A) (B)

Cl
Cl
, AlCl3
(C) (D)
AlCl3
107. With reference to the scheme given, which of the given statement(s) about T, U, V and W is (are) correct?
O
O

CH3 T
LiAlH4

CrO3/H (CH3CO)2O
V U excess W
(A) T is soluble in hot aqueous NaOH
(B) U is optically active
(C) Molecular formula of W is C10H18O4
(D) V gives effervescence on treatment with aqueous NaHCO3
108. Heating many alkyl chlorides or bromides in water converts them to alcohols through an SN1 reaction.
In which of the following sets of compounds, correct order of this solvolytic reactivity is shown.
Br
Br
Br Br Br
(A) < < (B) < <
Br

Br I Cl Cl Cl

(C) > (D) < >

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109. Which of the following primary amines can be prepared by the Gabriel synthesis.
NH2 NH2 NH2
(A) NH2 (B) (C) (D)

110. In which of the following pairs, second compound requires less energy for heterolytic cleavage of C – Xbond?

I
(A) Br (B) I
Br

(C) (D)
Br Br
I I
OH
Br2
111. CH2Cl2 ?
O
Identify the product(s)

OH O
O
(A) O (B) O (C) (D) HBr
O
Br
Br
Br
112. For the reaction, predict the major product(s)
(1) OsO4
(2) NaHSO3/H2O

H OH H OH

(A) (B)
OH HO

HO H HO H

(C) (D)
OH HO

CH3
Br2 H Br
113. A
CCl4 H Br
Cold
C2H5
KMnO4

Me
Me Et
(A) A is (B) A is
Et

CH3 CH3
H OH HO H
(C) B is H OH (D) B is H OH (Single product)
C2H5 CH3

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114. Which of the following gives positive iodoform test?

O OH
OH O
(A) (B) (C) (D)

115. Statement-1 : Tertiary nitrogen atoms at the bridgehead position of bridged bicyclic amines are often more
reactive as nucleophiles than are non cyclic tertiary amines.

Statement-2 : Alkylation of bridged bicyclic amine is faster than a non-cyclic tertiary amine.

N H3C–I
For Example : N
A bridge faster 
bicyclic amine H3C I

Et3N H 3C – I
Et3N – CH3 I
A non-cyclic
tertiary amine

(A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1

(B) Statement-1 is true, Statement-2 is true and Statement-2 is NOT the correct explanation for Statement-1

(C) Statement-1 is true, Statement-2 is false

(D) Statement-1 is false, Statement-2 is true

116. Statement-1 : In the reaction

HBr +
40ºC
Br
P1 Br P2
(major) (major)

Statement-2 :

P1 is formed by more stable carbocation intermediate.

(A) Statement-1 is true and Statement-2 is correct explanation for Statement-1.

(B) Statement-1 is true and Statement-2 is not correct explanation of Statement-1.

(C) Statement-1 is true, Statement-2 is false.

(D) Statement-1 is false, Statement-2 is true.

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Comprehension

Comprehension # 1

(C)
(Aldehyde)
Conc. H2SO4 1. O3
(A) (B)
 2. Zn/H2O
C6H14O
(1º-symmetric (D)
alcohol) (Ketone)

Oxime of Aldehyde (C) and oxime of ketone (D) show geometrical isomerism.

1. Pd/Charcol
117. (B) (P)
2. Br2/Light
3. KOH(alcoholic)

Compound (P) is :

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

Comprehension # 2 (Q. No. 118 and 119)

In the following sequence, various products are formed.

1. O2, h dil. OH, 

I J+K L
2. H O
3
118. The structures of compounds , I and J, respectively, are

OH
O
(A) , (B) ,

OH
O
(C) , (D) ,

119. The structures of compounds

K and L, respectively, are
OH
H H
H H
(A) , (B) ,
O O
O O
O O
O O H
(C) , (D) , OH

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Comprehension # 3 (Q.120 to Q.122)
On the basis of given scheme identify each of the compound

mild CH3COOH
(C) (A) (B)
oxidation dil.H2SO4 ester
(i) 50% KOH
(ii) H3O
(i) PCl5 
(A) + (D) (E) H – CN + H2O
(ii) NH3

120. Structure of (A) is

(A) MeOH (B) EtOH (C) CH3CH2CH2OH (D) HCOOH
121. Structure of (B) is

O O O O
(A) (B) (C) (D)
O O H O H O

122. Structure of (E) is

O
O O NH2
(A) (B) (C) (D) H N
NH2 H NH2 O
H
Comprehension 4 (Q.123 to Q.125) :

KOH(conc.) Benzyl 
(Q) + K Benzoate
 alcohol
1. O3 O
2. Zn/H2O
(P) O
dil. KOH HCN conc. H2SO4
(R) (S) (T)
5 – 10ºC 

123. T on hydrolysis gives which product :

OH OH OH
(A) (B)
HOOC HOOC

OH
OH
(C) HOOC (D)
HOOC
OH

( i) OH– /  (ii) LiAlH

124. S    4 V
 U   

(iii) HBr / 10C

In the above reaction sequence (U) and (V), respectively, are :

Br
CHO CHO
(A) and (B) and
Br

O Br O

(C) and (D) and

Br

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125. Reactant (P) is :

CH = C – CH3
(A) | (B) CH = CH – CH2CH2CH3
CH3

CH3

(C) CH = CH – CH3 (D)

CH = CH – CH
CH3
Comprehension : 5 (Q.126 to Q.128)
The polymer on reductive ozonolysis give compound (P) which one further reaction with dil NaOH give(Q)

polymer

126. Compound P does not give the following test

(A) tollen test (B) Felhing test (C) Lucas test (D) Iodoform test
127. Identify compound (Q)

O O CHO
COCH3
(A) (B) (C) (D)

128. Identify the monomer of the following polymer.

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

Comprehension 6 (Q.129 to Q.131)

An aromatic compound (P) (C10H10) on ozonolysis give (Q) and (R) in which (Q) give 2 mole CHI3 in presence
of NaOH / I2.
129. Identify (P) compound

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

130. Number of mole of CH3MgX consumed whenever react with (R)

(A) 2 (B) 3 (C) 4 (D) 6
131. Product Q and R can be differenciate by
(A) 2, 4-DNP (B) NaHCO3 (C) tollen (D) NaHCO3

Comprehension 7 (Q.132 to Q.134)

A tertiary alcohol (A) C7H14O on reaction with conc. H2SO4 gives (B) C7H12. (B) on ozonolysis give (C)
C7H12O2. (C) gives both Haloform and Tollen’s reagent test. When (C) reacts with sodium methoxide gives
OH

(D) C7H10O. (D) on reaction with H2 / Ni give (E) .(E) on reaction with conc. H2SO4 gives (B)

132. Structure of (A) is :

OH
OH OH OH

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

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133. Structure of (B) is :

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

134. Which statement is true about (D)

(A) Formed from cannizaro reaction (B) Formed from perkin reaction
(C) Formed from cross aldol reaction (D) Formed from intramolecular aldol reaction
Comprehension 8 (Q.135 to Q.136)
E2 reaction  Elimination bimolecular
In the general mechanism of the E2 reaction a strong base abstract a proton on a carbon atom adjacent to the
one of the leaving group. As the base abstracts a proton, a double bond forms and the leaving group leaves.

H CH3
CH3 – CH2 – CH – CH3 CH3ONa
  
 + +
| CH3OH
Br CH3 H
(major)

Mechanism :
 +
+
H CH3O H
 |
CH3ONa + CH3 – CH – CH – CH3  CH3 — CH –— CH — CH3 
|
Br (trans-2-butene)
Br
anti-coplanar transition state
(staggered conformation
-lower energy)
135. Give the correct order of rate of reaction with alc-KOH

Br Br
(i) (ii) Br (iii)

(A) (i) > (ii) > (iii) (B) (ii) > (i) > (iii) (C) (iii) > (ii) > (i) (D) (iii) > (i) > (ii)

O Cl

x PCl5 yNaNH2 CH3I

136.

O
CC–CH3
Sum of x + y ?
(A) 4 (B) 5 (C) 6 (D) 8

Comprehension 9 (Q.137 to Q.138)

HgSO4 (1) NaOI,H
(X) (Y) Propane
dil.H2SO4 (2) CaO/NaOH,
137. Structure of (X) is

(A) (B) (C) (D) All

138. Structure of (Y) is

O
(A) (B) (C) (D) All
O O

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Comprehension 10 (Q.139to Q.141)

H3O
( A )   (B) + (C)  gives positive iodoform test

LiAlH4


H
(D) 



139. Structure of (A) is

O
O
(A) (B) O
O

O
O
(C) (D) O
O

140. Structure of (C) is

OH OH
(A) (B) (C) OH (D)
OH

141. Relationship between compound (C) and (D) is

(A) Chain isomer (B) Positional isomer (C) Stereoisomer (D) None

Comprehension 11 (Q.142 to Q.144)

Following are structural formulas for two natural products isolated from plants of the chrysan thenum family.

H OH
O
H
CH3 || O
CO O
H O
H3C H
CH3 O O
C=C CH3 H CH3 CH2CH=CHCH=CH2
CH3C H C – CH3
|| O
O Pyrethrin-II
Pyrethrosin

142. The total sum of number of tetrahedral stereocentres and all carbon-carbon double bonds about which there
is the possibility for cis-trans isomerism in each molecule.
(A) 10 (B) 11 (C) 12 (D) 13

143. State the number of stereoisomers possible for molecules Pyrethrin-II.

(A) 16 (B) 32 (C) 64 (D) 128

144. State the number of stereoisomers possible for molecules Pyrethrosin.

(A) 16 (B) 32 (C) 64 (D) 128

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Comprehension 12 (Q.145to Q.147)

Trehalose is found in young mushrooms and is the chief carbohydrate in the blood of certain insects. Trehalose
is a disaccharide consisting of two units of D-glucose joined by a glycoside bond.

CH2OH
O
HO
HO
OH
CH2OH
O O
HO OH
OH
(Trehalose)

145. Which of the following statements are True (T) or False (F) regarding the compound Trehalose.
Statement-I : Trehalose is a reducing sugar.
Statement-II : Trehalose undergo mutarotation.
Statement-III : Trehalose react with Four moles of periodic acid.
Statement-IV : Both the glucose units joined through an -1,1-glycosidic linkage.
Choose the correct alternative :
(A) FTFT (B) FFTF (C) TTFF (D) FFTT

146. How many moles of acetic anhydride (Ac2O) consumed on reaction with Trehalose?
(A) 6 (B) 7 (C) 8 (D) 9

dimethyl sulfide
O
CH3–O–S–O–CH3

147. Trehalose O
Product ?
(excess)

CH2OH CH2OH
O O
MeO HO

(A) MeO (B) HO

OH OH
CH2OH CH2OH
O O O O
MeO OMe HO
MeO OH OMe

CH2OMe
O CH2OH
MeO
O
HO
MeO
(C) OMe (D) HO
OH
CH2OMe OCH3
O O
MeO OMe
OMe

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Comprehension 12 (Q.148 to Q.150)
A student in the lab had a mixture of three compounds, 4-methyl benzoic acid, 4-methylcyclohexylamine
and 1, 4-dimethyl benzene. In order to separate the three compounds the following extraction (separation)
scheme was followed. At the end of the procedure the student had six separate flasks containing either an
aqueous or an ether solution. Locate each compound by designating the flask expected to contain each
compound. Some relevant pKa data is given :

SCHEME
CO2H
CO2H NH2 CH3

CH3
CH3 CH3 CH3
pKa = 4.4

1. ether
2. HCl (aqueous)

ether aqueous

NaOH NaOH

aqueous ether ether aqueous

HCl 4
Flask : 3 HCl
Flask

aqueous ether
Flask : 1 Flask : 2 ether aqueous
5 6
Flask Flask
148. Which flask contains the 4-methyl cyclohexylamine?
(A) 2 (B) 3 (C) 4 (D) 5

149. Which flask contains the 4-methyl benzoic acid?

(A) 2 (B) 3 (C) 4 (D) 5

150. Which flask contains the 1, 4-dimethylbenzene ?

(A) 1 (B) 3 (C) 5 (D) 6

Comprehension 13 (Q.151 to Q.153) [+3, –1][9 × 3 = 27]

On the basis of given scheme identify each of the compound

O

C–O K
(1) CH3MgBr O3 Conc. KOH/
(A)  (B) (C)
(2) H3O Zn CH2OH
(3) H2SO4/
(D)

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151. Identify compound (A) is
O O

(A) H (B) CH3

O O

(C) (D)

152. Identify compound (B) is

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

153. Compound (C) do not give which type of reaction

(A) Tollen test (B) Cannizaro (C) Oxime formation (D) Aldol condensation

Comprehension 14 (Q.154 to Q.156)

On the basis of given scheme identify each of the compound

CH=O
O3 NaOH( aq.)
(A)  (B)   (C) 
H2 / Pd – C
 
Zn, H O
2


154. Structure of (A) is

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

155. Structure of (B) is

O O
O O
(A) O (B) (C) (D)
O O O
156. Structure of (C) is
CHO
(A) (B) CH=O

CH=O
COONa
(C) (D)
OH

Comprehension 15 (Q.157 to Q.159)

On the basis of given scheme identify each of the compound

NH3
(X) (Y) 2KOBr (Z)
 

OH
HO Terylene polymer
H ,

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157. Structure of (X) is

CO2H CO2H CO2H COOH

CO2H
(A) (B) (C) (D)
CO2H
CO2H
158. Structure of (Y) is

CONH2 CONH2 CONH2 CONH2

CONH2
(A) (B) (C) (D)
CONH2
CONH2

159. Structure of (Z) is

NH2 NH2 NH2 NH2

NH2
(A) (B) (C) (D)
NH2
NH2

Comprehension 16 (Q.160 to Q.161)

Br OCH3 OCH3
+ CH3 – OH  +
Ph Ph Ph
(+) (–) (+)
(Ethers)
This reaction takes place by both SN1 and SN2 mechanisms.
60% of (+)-1-Bromoethyl benzene reacts by SN1 and 40% of (+)-1-Bromoethyl Benzene reacts by SN2.
160. The product mixture obtained after the reaction is :
(A) dextro rotatory (B) levorotatory
(C) optically inactive (D) optical activity cannot be explained
161. What is the ratio (R/S) of both optically active ethers formed.
(A) 2 : 5 (B) 3 : 7 (C) 7 : 3 (D) 5 : 2
Comprehension 17 (Q.162 to Q.163)
+
conc.KOH H
(A) (B) O


O
162. Structure of (A) is

O O

(A) O (B) O (C) (D)

O
O O
O
163. Structure of (B) is
COONa COOH COOK

(A) (B) (C) (D) (A) and (C) both

OH OH OH

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Comprehension 18 (Q.164 to Q.166) :
The trisaccharide Raffinose occurs principally in cottonseed meal

OH
CH2OH
O
HO
OH

CH2
O
HO
HO
OH H
OH
O CH2OH
OH

CH2OH O H

164. Name the 3 mono saccharide units in raffinose respectively from top to bottom :

(A) glucose, galactose, fructose (B) galactose, glucose, fructose

(C) fructose, glucose, galactose (D) maltose, glucose, fructose

165. Describe glycosidic linkage from top to bottom :

(A) , ,  (B) , ,  (C) , ,  (D) , , 

166. With how many moles of Ac2O does raffinose react ?

(A) 9 (B) 10 (C) 11 (D) 12

Match the column

167. Column - I Column - II Column - III

(A) Polythene (P) Elastomer (J) Homopolymer

(B) Buna - S (Q) Fibres (K) Coplymer

(C) Nylon - 66 (R) Thermoplastic (L) Condensation polymer

(D) Bakelite (S) Thermosetting (M) Resin

168. Column I Column II

(A) Glucose (P) Osazone formation
(B) Sucrose (Q) Disaccharide
(C) Lactose (R) Reducing sugar
(D) Cellulose (S) Non-reducing sugar
(T) Mutarotation

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169. In column - I, statements are given and in column - II, structures are provided. Match the statement given in
column - I with corresponding structures shown in column - II

Column - I Column - II
OH
(A) An optically active compound that is oxidized (P)

by MnO2 to an optically inactive compound.

OH

(B) An optically active compound that is oxidized by (Q)

MnO2 to an optically active compound

OH

(C) An optically inactive compound that is oxidized (R)

OH
by MnO2 to an optically inactive compound

OH

(D) A compound that is not oxidized by MnO2 (S)

OH

OH

(T)

OH

170. Column-I Column-II

O
||
(A) Ph – C – CH 2 – Cl (P) SN1 & SN2 both reaction are possible

(B) CH3 – O – CH2 – Cl (Q) SN1 & SN2 both are not favorable

Cl

(C) (R) Only reactive toward SN1

CH2 – Cl

(D) (S) Only reactive toward SN2

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171. Column-I Column-II
NH2
| HNO2
(A) CH3 – CH2 – CH – CH3  Major products (P) Elimination reaction

H
(B) 
 (Q) Diastereomers is formed in the reaction

OH
HNO2
(C) NH2  Major products (R) Racemic mixture will formed

O (1) Mg(Hg)
(D)    (S) Carbocation is intermediate
(2 ) H2O

(T) Free radical intermediate

172. There are few reagents given in Column-I and some compounds given in Column-II. Match reagents (of
Column-I) with compounds (of Column-II) in which equilibrium of reactions is in forward direction.
Column-I Column-II
(A) Na (P) Ph – OH
(B) NaOH (Q) R – CO2H
(C) NaHCO3 (R) R – C  C – H
(D) NaNH2 (S) R – CH2 – OH
(T) Ph – SO3H

173. Column - I Column - II

(Moles of RMgx consumed)

O
(A) (P) 1
R – C – Cl

O
(B) (Q) 2
Cl – C – OEt

(C) R–CN (R) 3

O
(D) (S) 4
R R

174. Column - I Column - II

(A) Backelite (P) During addition polymerisation C–C bond formed
(B) P.A.N. (Q) During condensation polymerisation C–C bond formed
(C) Protein (R) During condensation polymerisation C–N bond formed
(D) Nylon-6,6 (S) Linear polymer
(T) Branch polymer

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175. Column I Column II
O
(A) (P) Yellow precipitate with NaOI.
CH 3 NH2

O
(B) (Q) Reacts with KOBr to form 1º amine
CH 3 CH3

O
(C) (R) Reduction to form 1º Amine.
Ph H
O
(D) (S) Reacts with LiAlH4 to form 1º Alcohol.

176. Match the chemical conversions in list-I with appropriate reagents in list-II and select the correct answer
using the code given below the lists :
Column-I Column-II

(A)  (P) CrO2Cl2

Cl

(B)  (Q) EtONa/EtOH

Cl

CH3 CHO

(C)  (R) t-BuO–K+/t-BuOH

COOH

(D)  (S) KMnO4

177. Column-I Column-II

Reactions Medium of Solution
CH3
CH3CH 2OH(aq)
(A) C – Br (P) Neutral

CH3

CH3CH 2OH(aq)
(B) Br (Q) Acidic

1. LiAlH4
(C) CH3 – CHO (R) Alkaline
2. H2O

OH

CH3COO¯Na+ (aq)
(D) (S) Acid - Base reaction.

SO3H
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178. Compound Laboratory Test
(A) Ph–NH2 (P) NaHCO3 test
(B) Ph–COOH (Q) 2, 4-DNP test
(C) PhCHO (R) AgNO3 + NH3OH test
OH
(D) (S) Br2 / H2O
COOH
(T) NaNO2 + HCl

179. Match the correct resonance energy of the compounds given in column-I
Column-I Column-II
(Resonance energy in kilocalories per mole)

(A) (Benzene) (P) 91

(B) (Naphthalene) (Q) 36

(C) (R) 83
(Anthracene)

(D) (S) 61

(Phenanthrene)

180. Match each of the compounds given in Column-I with the reaction(s), that they can undergo, given in Column-II.
Column-I Column-II

Br

(A) (P) Nucleophilic substitution

O

OH
(B) (Q) Elimination

CHO

(C) (R) Nucleophilic addition

OH

Br
(D) (S) Esterification with acetic anhydride
NO2
(T) Dehydrogenation

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181. List-I List-II
Cl
CH2
X1 Orlon Y1 H2C
n
CN

X2 Neoprene Y2 H2C–CH
n

X3 Terylene (Dacron) Y3 OOC COO–CH2–CH2

n

182. Column I Column II

Br2
(A) (P) Electrophilic addition
CCl4

Br2
(B) (Q) Free radical addition
h

(C) HBr (R) Free radial substitution

(D) DBr (S) Required resolution in product

(T) Product can show elimination reaction

Subjective

183. No. of cyclic hemiacetals (only pyranose form) are possible from D-Glucose and L-Glucose.
184. 0.037 gm of ROH was added to CH3Mg and the gas evolved measured 11.2 ml at STP. What is the
molecular wt. of ROH ? On dehydration ROH given as alkene which on ozonolysis gives acetone as one of
the products ROH on oxidation easily gives an acid containing the same number of carbon atoms. Give the
answer in the form (molecular weight of R–OH – 70).

185. x = Number of ether which give 2º alcohol on hydrolysis

(a) (b) (c) (d) (e) O

O O O O

186. How many of the following reaction schemes will produce a carboxylic acid ?
(1) O3 (2) H2O (1) BH3  THF
(A) (B)
(2) H2O2,NaOH
(1) O3 (1) BH3THF
(C) (D)
(2) DMSO (1) H2O2,NaOH

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 (E) N H3O /heat (F) KMnO4
H2SO4,H2O

(1) Mg OH
Br
Na2Cr2O7
(G) (2) CO2 (H) H2SO4, H2O
(3) H3O

Na2Cr2O7
(I) OH H2SO4, H2O

187. (i) C6H12 (3-membered ring) = a

(ii) C6H12 (4-membred ring) = b
(iii) C7H14 (4-membered ring) = c
What is relationship among a, b and c (strcutural isomers only).
(A) a + b = c (B) a + b + 1 = c (C) a + b – 1 = c (D) a + b – 2 = c

188. Number of pairs of identical molecules = ?

H3C H H CH3
(i) C=C & C=C
H3C Br Br CH3

OH
HO H HO H HO H
(ii) &
H H H H H

OH HF D
H D H
(iii) &
OH H F
HO
OH

H CH3
CH3 H

(iv) & CH3

H
CH3 H

Br H Br H Br CH3
(v) &
H CH3 CH3 CH3 Br H

CH3
H CH3
Cl
H Br
(vi) &
H Cl
H Br CH3
CH3

CH3 CH3
Br H H Br

(vii) &
H OH HO H
CH3 CH3
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 Br Cl Br Br Cl
(viii) Cl Br & Cl

CH3 H3C
CH3 CH3

H OH
(ix) &
HO H
Cl CH3

(x) CH3 CH2CH3 & H Cl

H CH2CH3

189. Identify number of pairs of diastereomers

Cl Cl Cl Cl
(i) &

Cl Cl Cl Cl

(ii) &
HO H H OH

(iii) &

O O
(iv) &

(v) &

Br Br
H
H Br
(vi) &
Br
H OH H OH OH
OH
Br Br
H
H Br
(vii) &
Br
H OH H OH OH
OH

Et H Me Me H Me H
(viii) &
Me Et H Et Et

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 CH2CH3

(ix) &

CH3
OH Br OH Br
(x) &

190. How many compound which has one of the stereoisomer as a meso compound

(a) (b) (c)

(d) 2, 3-dichlorobutane (e) 1, 2-dichlorobutane (f) 2, 3-dichloropentane (g) 2, 4-dichloropentane

191.  x = number of Resonating structure for given species is

O

192. x = number of distinct terminal alkyne with molecular formula C5H8 , then what is x = ?

Na
193. CH3 – Cl + C2H5 – Cl  (X) = number of dimerised products.
Dry ether

194. Cl Cl CH3 CH3

O | |
|| H Cl H Cl Cl
C
H H, , , H Cl , Cl H , ,
Cl Cl
| CH3 CH3
Cl
Number of molecules having plane of symmetry (POS) = x
Number of molecules having center of symmetry (COS) = y
Number of molecules having two fold axis of symmetry (C2) = z
So x + y + z = ?

195. How many compounds can undergo SN2 reaction more easily than SN1 ?
Cl
Cl
Cl
(a) Cl (b) CH3Cl (c) (d) (d)

Cl
H O
196. 2
SN1

Total alcohol products of the above reaction is/are

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197. Amongst the following, the total number of compounds soluble in aqueous NaOH is

H3C CH3
OCH2CH3 OH
N COOH
CH2OH
(a) (b) (c) (d)

OH CH2CH3 COOH
NO2
CH2CH3

(e) (f) (g) (h)

N
H3C CH3

CH3 Br
| | EtOH
198. CH3 – C – CH – CH3 total number of (SN1 + E1) products (Including stereoisomers)
| 
CH3

199. In given reactions x, y, z are number of  Hydrogen in major products. Then what is the value of x + y + z =
OH

(i) H (X) major (ii) H (Y) major

 
OH
OH
(iii)
H (Z) major


200. The total number of alcohol group in the product P is :

1. LiAlH4 (excess)
CN 2. H2O

O OH

xHIO4

201. All stereoisomers of D-glucose

yAc2O
(acetylation reaction)
Sum of number of moles of HIO4 (x) and acetic anhydride (y) consumed are

202. x = Number of dehydrating reagent

H2SO4, H3PO4 , Al2O3, P2O5, POCl3, HI, NaI, KBr

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203. x = moles of RMgX consumed

O
HO
Cl
OEt

O O

204. x = Number of compound not undergo SN1 reaction

I I I I

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

I I
I

(e) (f) (g)

205. x = no. of reaction in which end product is

Hg 2
(1) LiAlH4 HBr alc. KOH
(a) C  CH      (b) CH = CH2 ( A )  
dil. H2SO4 ( 2 ) H2SO 4 /  CCl4 

H2SO4
  H / 
(c) 
(d)  

OH
OH

alc. KOH
H /   
(e)  
 (f) 
OH
Cl

206. x = Number of Hoffman exhaustive methylation and elimination (HEMAE)

N
207. x = Number of Compound undergo Nucleophilic substitution reaction :
Cl Cl
Cl
(a) (b) (c) (d)
Cl
OH OH
(e) (f) (g) (h) O

F
F O
(i) Ph – O – CH3 (j) (k) (l)
NO2 Cl
NO2

Br
O Cl
NO2
(m) (n) (o) (p)
OEt Cl
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208. x = Number of ether which cannot prepared by Willamson ether systhesis.
O – CH3
(a) Ph – O – Ph (b) Ph – O (c)

O
(d) O – CH3 (e) O (f)

(g) O (h) O

209. How many compounds are soluble in sodiumhydroxide

(i) Ph – CH2 – OH (ii) Ph – OH (iii) R – CO2H (iv) Ph – SO3H
HO OH
(v) (vi) R – C  C – H

210. How many compounds react with Sodium bicarbonate

OH OH NH2

(i) CH3 – CO2H (ii) (iii) (iv)

OH
SO3H

(v) (vi)

NO2

211. How many compounds will undergo decarboxylation easily under mild conditions
COOH
COOH O O
O O O
(a) (b) (c) OH (d)
OH
O

COOH
COOH
(e) (f) COOH
COOH

212. x = Number of compound which gave carboxylic acid when react with CrO3 . H2SO4.
OH
(a) OH (b) (c) (d)
OH OH
OH
OH
OH
(e) (f) OH (g) (h)

OH OH
(i) (j) OH (k) (l)
OH

OH

(m) (n)
OH
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213. x = Number of alcohol which gave ketone by chromic acid?
OH
(a) (b) OH (c) (d)
OH OH

OH
(e) OH (f) (g) OH (h)
OH
214. x = Number of compound when reach with excess CH3MgBr followed by acidification give 3º alcohol.
O
O || O
|| O ||
(a) Et (b) (c)
O Cl

O O
O || ||
(d) || (e) H – C – O – Et (f) H – C – Cl
O O O
|| || ||
(g) (h) CH3 – C – O – C – CH3 (i)
NH2 O O
O O
|| ||
(j) Cl – C – O – Et (k) S O (l)
O

xEtOH y EtOH
215. (i)   Acetal
al (ii)   Acetal
 H
H O

x & y are moles consumed.

x+y=?

216. x = Number of carbocation more stable than (sec. butyl carbocation) is/are
y = Number of carbocation which undergo rearrangement

O O

(a) (b) (c)

(d) (e) (f)

O O
NH
(g) (j) (k)
(h) (i)

217. x = number of compound which gives racemic mixture with HBr. What is value of x?
OH CH3
CH2
(a) (b) (c) (d)
OH

CH2
(e) (f) (g) (h) (i)

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218. How many compound give ketone when reacts with Hg+2/H2SO4
(a) HC  CH (b) CH3 – C  CH (c) Ph – C  CH (d) Ph – C  C – Ph
(e) CH3 – CH – C  CH (f) CH3 – CH2 – C  CH (g) CH3 – C  C – Et

CH3

219. If w = number of compound reacts with NaHCO3.

x = number of compound soluble in NaOH.
y = number of compound reacts Na-metal to evolve H2 gas.
z = number of compound reacts with FeCl3.
Then find out value of (w + x + y + z) =
OH
CO2H SO3H OH O2N NO2

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

NO2

OH OH
OH NO2

(e) (f) CH3 – C  CH (g) (h)

NO2 CH3

CO2H CH2 – OH CH2OH

(i) (j) (k)

220. x = number of compound undergo esterification reaction with EtOH.

y = number of compound undergo formation of hemiacetal with EtOH.
Find out the value of (X + Y)
O O
O O
O
(a) CH3 – C – O – C – CH3 (b) (c) (d) OH
CH3 – C – Cl

O O O O O
(e) (f) (g) (h)
CH3 – C – H Ph – C – Cl Ph – C – O – C – Ph
CH3
Cl
(i) CH (j) CH3 – CH2 – OH
3
CH3

221. If x = number of compound reacts with LiAlH4

y = number of compound reacts with NaBH4
z = number of compound reacts with LiAlH4 to form alcohol
then find out value of (X + Y + Z) = ?
O O
(a) (b) (c) (d) H2C = O
O

O O NO2
O O
(e) O (f) (g) O (h) (i)
NH2 Cl

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222. x = Number of compound undergo alkaline hydrolysis.
y = Number of compound react with DIBAL-H to form aldehyde.
Then find the value of x + y
O
(a) CH3 – C  N (b) (c) CH3 – O – CH3 (d) CH3 – CH2 – OH
O – CH3

O
O
(e) (f) H2C = CH2 (g) O (h) CH3 – CH3
CH 3 – C – Cl

alc.KOH H2O
223. E2 products = X Br w = SN1 products

E2 products = Z alc. KOH H2O y = SN1 products

Br

Sum of w + x + y + z is

xH 
224. Et – O – Et 

yH 
Ph – O – Et 

zH
Ph – O – Ph 

x,y and z are moles of HI consumed
Sum of x + y + z ?

225. x = Number of reaction in which retention of configuration take place.

Value of x is

Cl

K SH
(a) (b) K SH + CH3 – Cl

CH3 Et
Na SOCl2
(c) H OH (d) H OH

Et CH3

CH3 CH3
SOCl2 PCl5
(e) H OH (f) H OH
Pyridine
Et Et

CH3
TsCl
(g) H OH
Pyridine
25ºC
Et

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226. x = Number of reaction in which racemic mixture will formed
y = Number of reaction in which carbocation will formed as intermediate
Find out the value of (x + y) is
O O
|| LiAlH4
(a) Ph – C – CH3 (b) LAH

CH3
LiAlH4 H2O
(c) (d) Ph Cl
O
Et

CH3 CH3
+
H3O conc-HI
(e) Ph OCH3 (f) Ph OH

Et Et

OH O
+ –
conc-HI (1) K CN
(g) (h)
H (2) H+

227. In given reactions x, y, z are number of  Hydrogen in major products. Then what is the value of x + y + z =
OH

(i) H (X) major (ii) H (Y) major

 
OH
OH
(iii)
H (Z) major


228. Among the following biomolecules, how many have glycosidic bond ?
(a) Protein (b) Starch (c) Glucose (d) Fructose (e) Sucrose (f) Maltose

OH

229. x = no. of reaction in which one of the last product is

Cl

CH = O CO2H

conc. KOH
(a)   (b)  

LiAlH
4


Cl Cl

CO2H Br

(c) DBAL H (d) aq. KOH

  
  
Cl Cl

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230. x = Number of compound which are o/p director.
Cl NH2 N=O NO2

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

O
O
NH – C – CH3 NH2
(e) (f)

O
CH3 SO3H

(g) (h) (i)

231. In the given scheme below, the total number of intramolecular aldol condensation products
(excluding streoisomer) formed from 'X' is
CH3
3(i ) O NaOH( aq)
    (X)   
( ii) Zn, H2O heat

232. How many different types of products possible (including streoisomer) from reductive ozonolysis of given
compound.

OH

NaNO 2 /
LiAlH4
conc. HNO3 HCl
233.  (A)    (B)   
 (C) (D)
(or ) Sn / HCl mild-basic
condition
Double bond equivalent of D is

234. x = no. of compound which reacts with HCN then followed by acidification. Lactonization take place

O O O O
C–H C–H
(A) (B) (C) (D)

OH OH OH

O
OH
(E) (F)
OH
OH

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235. x = Number of reaction in which new cyclic ring in product will form.
Cl Cl
AlCl3 AlCl3
(a) (b) O

O O
(c) H – C – C – C – C – C – OH H (d) H – O – C – C – C – C – C – OH H
 
(e) H2C = CH – C – C – C – OH (f) H2C = CH – C – C – C HBr
H
CCl4
CH2–OH
H2O H
(g) SH H (h)

H Cl C–OH
O

O
O
OH H2SO4 H2SO4
(i) (j) + O


O
O O O
(k) PhMgBr (L) KOH/
Cl

236. x = Number of reaction in which carbocation is intermediate.

y = Number of substituion reaction.
HNO3 OH H2SO4 OH HI
(1) (2) (3)
H2SO4 
O O
H2O
(4) I (5) KOH (6) CH3MgBr


Cl O OH

(7) AlCl3 (8) AlCl3 (9) Br2

+ +
Cl H2O

OH OH
– –
(10) Ph – N  NCl (11) CHCl3 / OH
Mild-basic

237. x = Number of compound which gives positive iodoform test

O O OH
(i) (ii) (iii) (iv) (v)
OH
O
O
(vi) Ph – CH = CH – C – CH3 (vii) Ph – CH = CH – CH2 – OH (viii) Ph – CH = CH

OH
O CH2 – OH
(ix) I (x) (xi) O (xii)
OH

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 OH
O A (Major)
Br 2/H2
238. Br /C
2 S 2
B (Major)
Calculatge (X + Y) where X = number of bromine atoms in A, Y = number of bromine atoms in B.

239. How many atoms groups withdraw the electrons from benzene ring ?
(a) – NO2 (b) – CN (c) – CO2H (d) –CHO (e) –Et (f) –SO3H (g) –N(CH3)2 (h) – N+(CH3)3

Y Ph – NH – NH2
Glucosazone

240. D (+) – Glucose

O O
Z O
y+z=? Acetate derivative

CHO
H OH
241. HO H
(Ac)2O
H OH
H OH
OH
In above reaction, identify moles of (Ac)2O consumed

242. Identify the number of monochlorination product.

Cl2
CH3 – CH2 – CH – CH2 – CH3  (x)
| hv
CH3

243. (a) Identify the number of product (including stereo) sum of x + y + z.

O
O ||
|| NH2 OH NH OH
Ph – C – CH 3      (x) ; Ph – CH 2 – C – H  2 (y)
O
|| NH OH
H – C – H  2 (z)
(b) Number of compound undergo hydrazone formation.
O O O O O
O
(a) (b) (c) (d) (e) (f)
Cl OEt OH
244. Calculate total possible monochlorinated products for the following hydrocarbons (consider only structural
isomers).

(P) (Q) (R) (S)

The sum of P + Q + R + S – 15 = X. Find X

O
CO2H
H3O LiAlH4 Dil.KMnO4
245. CO2H  (B) HCN (C) (D) (E) (F)
excess
(A)
Find the total number of –OH group present in compound (F) ?

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 CO2H
Br2
246. (A) Meso
CCl4
HO2C

1. Zn(Hg) Conc.H2SO4/ Hot alk. KMnO4

(B)  (C) (D) (E) (F)
AlCl3 2. H2/Pd-C
If (B) is stereoisomer of (A). Find the number of –COOH group in compound (F) ?

O3 Ca(OH)2 EtOH(excess)
247. (B) (C) (D)
H2O2 
/H
(A)
x = Number of ether functional group in compound (D)
y = Moles of NaHCO3 reacts with compound (B).
Find sum of x + y = ?

O3 H2/Pd–C Cl2/h
248. (A) KOH/ (B) (C) Se (D) Zn (E) (F)
CH3–S–CH3 (excess)
aq.KOH
(G)
(1) NaOH(CaO),
(2) H

(H)

X mole of acetylene gives compound (H). What is the value of X ?

O O O O O
249. R–C–O–R, R–CN, R – C – NH2 , R – C – Cl , CH3–C–O–C–CH3 , CH3 – O – CH3
(a) (b) (c) (d) (e) (f)
x = Number of compound reacts with LiAlH4 to give alcohol
y = Number of compound reacts with undergo alkaline hydrolysis
Find the value of x + y – 7 ?

250. Amongst the following, the total number of compound soluble in aqueous NaOH is :

OH OH COOH OH

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

CH3

NO2 COOH O

(e) (f) (g) (h) OH

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251. How many compound given below are O/P directors ?
OH NO2 OCH3 CH3

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

SO3H NH2 Cl CO2H

(e) (f) (g) (h)

252. Number of isomeric alcohols having molecular formula C4H10O which can be prepared by hydrogenation of
carbonyl compound (aldehyde and ketone). (Include stereo isomers)

253. x = number of compound undergo Hoffmann bromamide reaction. What is value of x?

O O O O
(a) R – C – NH 2 (b) Ph – C – NH 2 (c) Ph – C – NH – Br (d) Ph – C – NH – CH3
O
O O
Me
(e) Ph – C – N (f) Ph – C – NH – Et (g) Ph – NH2 (h) NH2
Me
O

NH2
(i)

CHO
254. Ac2O, 2CH3MgBr
– (B) H (C) (D)
AcO /
OH
(A)
Total number of alcohol group in compound (D) ?

O
O O
LiAlH4 xAc 2O
255.    (A)    (B)

Identify the value of x is :

256. x = no. of compound which reacts with excess of CH3MgBr to form 3° alcohol.
O O
(a) (b) O (c) (d)
O OEt
O O O
(e) H – C – OEt (f) Ph – C – Cl (g) H – C – Cl (h) CH3 – C  N
O
(i) EtO – C – OEt

257. ( x ) NaNH2 ( Y ) CH3 – 

Ph – CH – CH2    (A)     Ph – C  C – CH3
Br Br
(x) and (y) are moles of NaNH2 and CH3 – I respectively then what is the value of x + y?

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 +2 –
Hg LiAlH4 O3 D2O/DO ND2–OD/
258. C  CH (B) (C) H / (D) (E) (G) (F)
(A) H 2 SO 4 Zn Prolonged
Number of deuterium in F is (x).
OH

(1) KOBr Ph–NN Cl (1) CHCl3/KOH LiAlH4

(B) (C) (D) (E)
(2) H mild-basic (2) H
259. medium (3) CHCl /KOH
O (4) H
NH2
(A)
Number of alcohol group present in compound (E) is (a).
Number of 2º amine group present in compound (E) is (b).
a+b=?

Br
260. (a) Br2 + h Total number of dibromo products (only structural) = (X)

Cl2/h
(b) Total number of monochloro products (only structural) = (Y)

Sum of (X + Y) = ?

261. Total number (X + Y) of chiral centres in aldopentose (X) and ketopentose (Y) are :

262. x = no. of compound reacts with Na/Liq. NH3 to from trans alkene
Ph Ph Ph

(a) (b) (c) (d) (e) (f)

263. O COOC2H5

When the above molecule is reduced with excess LiAlH4 followed by dilute acid hydrolysis, how many
organic products can be isolated by fractional distillation of product mixture.

264. How many following compound can give precipitate of iodoform by reacting with NaO
OH
O O
(a) CH3 – CH2 – C – CH2 – C – CH2 – CH3 (b) (c)
O O HO OH
(d) CH2 – CHO (e) CH3 – CH2 – OH (f) CH3 – CH – CH2 – CH3

Cl
O O
(g) Ph – CH 2 – C – CH 3 (h) CH 3 – C – NH – Et

265. HBr (X) alc.KOH (Y) , Identify the number of E2 product in 'Y'.

major product

266. A compound (A) C4H10O4 yields on acetylation (B) of formula C12H18O. How many hydroxyl groups are
present in compound ? Also write structures of (A) and (B).

267. Number of isomeric alcohols of C5H12O which do not show oxidation with KMnO4.

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 H 2SO 4
268. x

x = number of possible alcohol.

O–Ph

269. OH
x HI
OH

OH

X is the number of moles of HI consumed by given compound.

270. A decapeptide (Mol. wt. 796) on complete hydrolysis gives glycine (Mol. Wt. 75), alanine and phenylalanine.
Glycine contributes 47.0% to the total weight of the hydrolysed products. The number of glycine units
present in the decapeptide is :

271. When the following aldohexose exists, the total number of stereoisomers in its furanose form having
D-configuration are :

CHO

CH2
CHOH
CHOH
CHOH
CH2OH

272. A tetrapeptide is formed by four different amino acids (G,A,V,L). If one of the amino acids always occupy the
ends of the peptide, how many sequence of tetrapeptide are possible ?
273. State the number of compounds which are aromatic among the following compounds :

H H H H

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


H H

H H H H H H
H H
H H
B  B H
(e) H – H (f) H H (g) H (h)
H H H H
H H
H H

 
(i) (j)

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274. (A) + Ac2O (B)
mol.wt(x) (acetic anhydride) mol.wt = (x+210)
Number of (OH) group present in (A) is

15 15
CONH2 CONH2 CONH2
14
275.
+ + Br2
Product(s)
KOH/
D
D

Can be

15 15 15 15
NH2 NH2 NH2 NH2 NH2 NH2 NH2 NH2 NH2
14 14 14 14

D D D D D
D D D (4) (5) (6) (7) (8) (9)
(1) (2) (3)

How many compounds among 1 to 9 can be products of the above reaction ?

276. The total number of hydrogens that can be anti-periplanar to bromine (the leaving group)

Br
H

277. How many carbonyl compound will give aldol condensation reaction
O

(a) CH3 – CHO (b) (c)

O

CHO
(d) CH3 – CH2 – CHO (e) CH3 – CH2 – C – CH3 (f)
O

278.

(X) Number of product.

(Y) Number of stereoisomer possible for product
x+y=?

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279. P = Number of anti-aromatic compound :
CH3
O
N

N O

Q = Total number of resonating structures of carbonate ion [CO32–]

H3C  CH3

R = Number of -hydrogen in given carbocation

S = Total number of geometrical isomers of

CH3 – CH = CH – CH = CH2
T = Number of compound more acidic then CH3CH2OH
OH OH

, , CH3COOH , CH3SO3H

NO2
Sum of (P + Q + R + S + T) – 15 is :

280. Among the six possible structural isomers of molecular formula C6H12 (containing cyclopropane ring), total
number of structures that are capable to show Geometrical isomers are x. Find x?

(1) (2) (3) (4) (5) (6)

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 Answer Key
Single Correct Choice Type :
1. D 2. D,E 3. B 4. E 5. A 6. D 7. B

8. D 9. E 10. B 11. B 12. A 13. C 14. C

15. D 16. E 17. A 18. B 19. B 20. C 21. B

22. A 23. A 24. A 25. D 26. C 27. A 28. C

29. A 30. C 31. A 32. B 33. C 34. D 35. C

36. C 37. B 38. C 39. B 40. C 41. B 42. C

43. C 44. B 45. D 46. A 47. A 48. C 49. E

50. A 51. C 52. A 53. B 54. B 55. A 56. E

57. C 58. D 59. C 60. C,D 61. C 62. B 63. C

64. A 65. C 66. B 67. C 68. C 69. A 70. B

71. B 72. A 73. A 74. A 75. A 76. B 77. A

78. A 79. A 80. D 81. B 82. A 83. C 84. C

85. C 86. B 87. B 88. C 89. C 90. C 91. C

92. C 93. D 94. C 95. C 96. A

Multiple Correct Choice Type :

97. A,B,C,D 98. A,C,D 99. C,D 100. B,C,D 101. A,D

102. A,C 103. A,C,D 104. A,B 105. A,B,C,D 106. A,B,C,D

107. A,C,D 108. A,D 109. A,B,C 110. B,D 111. A,C,D

112. A,D 113. A 114. A,B,C,D 115. B 116. D

Comprehension
117. A 118. C 119. C 120. A 121. B 122. B 123. C

124. A,B 125. C 126. C 127. A 128. B 129. A,C 130. A

131. C 132. B 133. B 134. D 135. A 136. C 137. A,C

138. A,C 139. B 140. B 141. B 142. B 143. B 144. C

145. B 146. C 147. C 148. C 149. A 150. B 151. B

152. B 153. D 154. D 155. C 156. D 157. C 158. A

159. A 160. A 161. C 162. A 163. C 164. B 165. A

166. C

Match the column

167. (A - R, J) ; (B - P, K) ; (C - Q, K, L) ; (D - S, K, L, M)

168. A  P,R,T ; B  Q, S ; C  P, Q, R ,T ; D S

169. A – Q, T ; B – R, ; C – S ; D – P

170. AS ; B P ; CQ ;DP

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171. A – R,S; B – P,Q,S ; C – R,S ; D – T

172. A – P,Q,R,S,T; B – P,Q,T; C – Q,T; D – P,Q,R,S,T

173. (A - Q) ; (B - R) ; (C - P) ; (D - P)

174. A – Q, T ; B – P, S ; C – R, S ; D – R, S

175. A  Q, R ; B  P ; C  S ; D P

176. A  Q ; B  R ; C  P ; D S

177. A  Q ; B  P ; C  R ; D S, Q

178. A  S, T ; B  P ; C  Q, R, S ; D P, S

179. A–Q;B–S;C–R;D–P

180. (A)  P, Q, T ; (B)  P, S, T ; (C)  R, S ; (D)  P

181. A

182. A  P,S,T ; B  R,S,T ; C  P,T ; D P,S,T

Subjective
183. 4 184. 4 185. 3 186. 5 187. a = 6, b = 4, c = 8 188. 6

189. 8 190. 3 191. 3 192. 2 193. 3 194. 14 195. 2

196. 3 197. 4 198. 6 199. 26 200. 2 201. 160 202. 5

203. 6 204. 3 205. 5 206. 3 207. 11 208. 3 209. 4

210. 3 211. 3 212. 4 213. 3 214. 8 215. 3

216. x=8 y=4 217. 4 218. 6 219. 27 220. 8 221. 21

222. x=4 y=4 223. 11 224. 3 225. 3 226. 11 227. 26

228. 3 229. 3 230. 5 231. 3 232. 4 233. 9 234. 4

235. 9 236. x=6 y=8 237. 6 238. 4 239. 6 240. 8

241. 5 242. 8 243. 5 244. 7 245. 4 246. 2 247. 4

248. 3 249. 1 250. 4 251. 5 252. 4 253. 5 254. 1

255. 3 256. 5 257. 4 258. 8 259. 2 260. 8 261. 5

262. 2 263. 3 264. 7 265. 3 266. 4 267. 1 268. 2

269. 2 270. 6 271. 8 272. 6 273. 5 274. 5 275. 3

276. 1 277. 4 278. 4 279. 4 280. 2

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