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Vidyamandir Classes: Innovating For Your Success
JEE Advanced-2022
Selected Question for Revision | Organic Chemistry-II
1. During dehydration of alcohols to alkenes by heating with concentrated H2SO4 the initiation step is :
(A) protonation of alcohol molecule (B) formation of carbocation
(C) elimination of water (D) formation of an ester
2. p-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide
to form the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the
carboxylic acid is :
(A) (B) (C) (D)

3. The best reagent to convert pent-3-en-2-ol into pent-3-en-2-one is :
(A) acidic permanganate (B) acidic dichromate
(C) chromic anhydride in glacial (D) pyridinium chlorochromate
4. Phenol, when it first reacts with concentrated sulphuric acid and then with concentrated nitric acid,
gives :
(A) nitrobenzene (B) 2, 4, 6-trinitrobenzne
(C) o-nitrophenol (D) phthalic acid
5. From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous
ZnCl2, is:
(A) 1-butanol (B) 2-butanol (C) 2-methylpropan-2-ol (D) 2-methylpropanol
6. Phenol is heated with a solution of mixture of KBr and KBrO3 . The major product obtained in the above
reaction is :
(A) 2-bromophenol (B) 3-bromophenol
(C) 4-bromophenol (D) 2, 4, 6-tribromophenol
7. Ortho-nitrophenol is less soluble in water than p- and m-nitrophenols because :
(A) o-nitrophenol shows intramolecular H-bonding
(B) o-nitrophenol shows intermolecular H-bonding
(C) melting point of o-nitrophenol is lower than those of m- and p-isomers
(D) o-nitrophenol is more volatile in steam than those of m- and p-isomers
8. Arrange the following compounds in order of decreasing acidity :
(A) IV > III > I > II (B) II > IV > I > III
(C) I > II > III > IV (D) III > I > II > IV
VMC | Revision Assignment 1 Organic Chemistry-II | JEE-2022

9. Consider the reaction sequence below :
(A) (B) (C) (D)
10. The product of the reaction given below is :
(A) (B) (C) (D)
11. In the following reaction sequence

KOH (aq.) 3 (i) CH MgBr
2 Anhy. ZnCl Conc. HCl
I  II 
   III 
 gives turbidity immediately
(C3H6Cl2 ) (ii) H2O /H
The compound I is :
Cl
|
(A) CH2  CH  CH3 (B) CH3  C  CH3
| | |
Cl Cl Cl
(C) Cl  CH  CH2  CH3 (D) CH2  CH2  CH2
| | |
Cl Cl Cl
12. The major product of the following reaction is :
(A) (B) (C) (D)
13. Phenol on treatment with CO 2 in the presence of NaOH followed by acidification produces compound X
as the major product. X on treatment with (CH3CO)2 O in the presence of catalytic amount of H 2SO 4
produce :
(A) (B) (C) (D)

14. Phenol reacts with methyl chloroformate in the presence of NaOH to form product A. A reacts with Br2 to
form product B. A and B are respectively:
(A) (B)
(C) (D)
15. The major product formed in the following reaction is :
(A) (B) (C) (D)
(A) (B) (C) (D)

17. On treatment of the following compound with a strong acid, the most susceptible site for bond cleavage
is:
(A) C4  O5 (B) O2  C3 (C) O5  C6 (D) C1  O2

18. The total number of optically active compounds formed in the following reaction is :
(A) four (B) two (C) six (D) zero
19. The products formed in the reaction of cumene with O2 followed by reactant with dil. HCl are:
(A) (B)
(C) (D)

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

21. The compounds A and B in the following reaction are, respectively :
(A) A = Benzyl chloride, B = Benzyl isocyanide

(B) A = Benzyl chloride, B = Benzyl cyanide
(C) A = Benzyl alcohol, B = Benzyl isocyanide
(D) A = Benzyl alcohol, B = Benzyl cyanide
22. The major product of following reaction is :

(1) AlH(i  Bu)
2
R  C  N  ?

(2) H2O
(A) RCOOH (B) RCONH2 (C) RCHO (D) RCH2NH2
(A) (B) (C) (D)

24. Which is the most suitable reagent for the following transformation ?
OH
|
CH3  CH  CH  CH2  CH  CH3  CH 3  CH  CH  CH2CO2H
(A) alkaline KMnO 4 (B) CrO2Cl2 /CS 2
(C) I2 / NaOH (D) Tollen’s reagent
OH
|
25. CH3CH2  C  CH3 cannot be prepared by :
|
Ph
(A) HCHO  PhCH(CH3 ) CH2MgX (B) CH3CH 2COCH3  PhMgX
(C) PhCOCH2CH3  CH 3MgX (D) PhCOCH3  CH 3CH 2MgX

(A) (B) (C) (D)
27. What will be the major product when m-cresol is reacted with propargyl bromide (HC  C  CH2Br) in
presence of K 2CO3 in acetone?
(A) (B) (C) (D)
28. The major product of the following reaction is:
(A) (B) (C) (D)
(A) (B) (C) (D)

(A) (B) (C) (D)
31. An organic compound neither reacts with neutral ferric chloride solution nor with Fehling solution. It
however, reacts with Grignard reagent and gives positive iodoform test. The compound is :
(A) (B)
(C) (D)
32. Consider the following reactions :
‘A’ is :
(A) CH 3  C  C  CH3 (B) CH 3  C  CH
(C) CH 2  CH 2 (D) CH  CH
33. Arrange the following compounds in increasing order of C  OH bond length :
methanol, phenol, p-ethoxyphenol
(A) methanol < p-ethoxyphenol < phenol
(B) phenol < p-ethoxyphenol < methanol
(C) phenol < methanol < p-ethoxyphenol
(D) methanol < phenol < p-ethoxyphenol
34. 1-methyl ethylene oxide when treated with an excess of HBr produces:
(A) (B) (C) (D)

35. In the following reaction sequence, structures of A and B, respectively will be:
(A) (B)
(C) (D)
36. The major product [B] in the following sequence of reactions is:
(i) B H
2 6 2 4 dil. H SO
CH3  C  CH  CH2CH3  [A]   [B]
| (ii) H2O2 ,OHΘ 
CH(CH3 )2
CH3  C  CH  CH2CH3 CH2  C  CH2  CH2CH3

(A) | (B) |
CH(CH3 )2 CH(CH3 )2
CH3  C H  CH  CH  CH3
(C) | (D)
CH(CH3 )2
37. Consider the following reaction:
Chromic

anhydride
 'P '
The product ‘P’ gives positive ceric ammonium nitrate test. This is because of the presence of which of
these – OH group(s)?
(A) (b) only (B) (d) only
(C) (b) and (d) (D) (c) and (d)
38. The increasing order of boiling points of the following compounds is :
(A) I < IV < III < II (B) IV < I < II < III
(C) III < I < II < IV (D) I < III < IV < II

39. When neopentyl alcohol heated with an acid, it slowly converted into an 85 : 15 mixture of alkenes A and
B, respectively. What are these alkenes ?
(A) (B)
(C) (D)
40. The major product in the following reaction is:
(A) (B) (C) (D)
41. The major aromatic product C in the following reaction sequence will be:
(A) (B)
(C) (D)
42.  
An organic compound ‘A’ C9H10O when treated with conc. HI undergoes cleavage to yield compounds
‘B’ and ‘C’ . ‘B’ gives yellow precipitate with AgNO3 where as ‘C’ tautomerizes to ‘D’. ‘D’ gives positive
idoform test. ‘A’ could be:
(A)
(B)
(C)
(D)

43. Two compounds A and B with same molecular formula  C 3 H6 O  undergo Grignard’s reaction with
methylmagnesium bromide to give products C and D. Products C and D show following chemical tests.
Test C D
Ceric ammonium nitrate test Positive Positive
Lucas Test Turbidity obtained after five Turbidity obtained immediately

minutes
Iodoform test Positive Negative

C and D respectively are:
(A) (B)
(C) (D)
44. A solution of phenol in chloroform when treated with aqueous NaOH gives compound P as a major
product. The mass percentage of carbon in P is________. (to the nearest integer)
(Atomic mass: C = 12; H = 1; O = 16)
45. Consider the following reactions:
(A)
(B)
(C)
(D)

46. A compound ‘X’ containing C, H and O is unreactive towards sodium. It does not add with bromine.
On refluxing with an excess of HI, ‘X’ yields only one organic product ‘Y’. ‘Y’ on hydrolysis yields a new
compound ‘Z’ which can be converted into ‘Y’ by reaction with red phosphorus and iodine. The compound
‘Z’ on oxidation with potassium permanganate gives a carboxylic acid. The equivalent weight of acid is 60.
What are the compounds ‘X’, ‘Y’ and ‘Z’? Write chemical equations leading to the conversion of ‘X’ to ‘Y’.
47. An industrial method of preparation of methanol is:

(A) catalytic reduction of carbon monoxide in presence of ZnO  Cr2O3
(B) by reacting methane with steam at 900°C with nickel catalyst
(C) by reducing formaldehyde with LiAlH4
(D) by reacting formaldehyde with aqueous sodium hydroxide solution
48. When phenol is treated with excess of bromine in water, it gives :

(A) m-bromophenol (B) o- and p-bromophenol
(C) 2, 4-dibromophenol (D) 2, 4, 6-tribromophenol
49. A compound of molecular formula C7 H8O is insoluble in water and dilute sodium bicarbonate
but dissolve in dilute NaOH solution and gives a characteristic colour with FeCl3. On treatment
with bromine water, it readily gives a precipitate of C7H5OBr 3 . Write down the structure of
the compound.
50. Arrange the following in increasing order of boiling point: n-butane, n-butanol, n-butylchloride,
iso-butane.
51. Phenol reacts with bromine in carbon disulphide at low temperature to give :
(A) m-bromophenol (B) o- and p-bromophenol
(C) p-bromophenol (D) 2, 4, 6-tribromophenol
52. The product of combustion of an aliphatic thiol (RSH) at 298 K are :

(A) CO2 (g), H 2 (g) and SO 2 (g) (B) CO2 (g), H 2O( ) and SO 2 (g)
(C) CO 2 ( ), H 2O( ) and SO2 (g) (D) CO 2 (g), H 2O( ) and SO2 ( )
53. Aliphatic ethers are purified by shaking with a solution of ferrous salt. Comment upon
the statement.
54. Compound X (molecular formula, C5H8O) does not react appreciably with Lucas reagent at room
temperature but gives a precipitate with ammoniacal silver nitrate. With excess of MeMgBr, 0.42 g of X
gives 224 mL of CH4 at STP. Treatment of X with H2 in presence of Pt catalyst followed by boiling with
excess HI, gives n-pentane. Suggest structure for X and write the equation involved.
55. Amongst the three isomers of nitrophenol, the one that is least soluble in water is _______.
56. Complete the following with appropriate structures :
57. Identify C(C4 H8 ) which when treated with H 2O/ H2SO4 gives C4 H10O which cannot be resolved into
optical isomers.
58. An optically active alcohol A (C6 H10O) absorbs two moles of hydrogen per mole of A upon catalytic
hydrogenation and gives a product B. The compound B is resistant to oxidation by CrO3 and does not
show any optical activity. Deduce the structures of A and B.

59. The order of reactivity of the following alcohols towards concentrated HCl is :
I. II. III. IV.
(A) I > II > III > IV (B) I > III > II > IV
(C) IV > III > II > I (D) IV > III > I > II
60. Give reason for the following: Although phenoxide ion has more number of resonating structures than
benzoate ion, benzoic acid is a stronger acid than phenol.
*61. The following ether, when treated with HI produces :
(A) (B) (C) (D)
62. An organic compound P having the molecular formula C5H10O when treated with dil H2SO4 gives two
compounds, Q and R both gives positive iodoform test. The reaction of C5H10O with dil, H2SO4 gives
reaction 1015 times faster than ethylene. Identify organic compound Q and R. Give the reason for the
extra stability of P.
63. (I) 1, 2-dihydroxy benzene (II) 1, 3-dihydroxy benzene
(III) 1, 4-dihydroxy benzene (IV) Hydroxy benzene
The increasing order of boiling points of above mentioned alcohols is :

(A) I < II < III < IV (B) I < II < IV < III
(C) IV < I < II < III (D) IV < II < III
PARAGRAPH FOR QUESTIONS 64 - 66
Reimer-Tiemann reaction introduces an aldehyde

group, on to the aromatic ring of phenol, ortho to the
hydroxyl group. This reaction involves electrophilic
aromatic substitution. This is a general method for
the synthesis of substituted salicylaldehydes as
depicted below.
64. The structure of the intermediate I is :
(A) (B) (C) (D)
65. The electrophile in this reaction is :

 CHCl 
(A)  (B) CHCl
 CCl 
(C)  2 (D) CCl3
66. Which of the following reagents is used in the above reaction?

(A) aq. NaOH  CH3Cl (B) aq. NaOH  CH 2Cl 2
(C) aq. NaOH  CHCl 3 (D) aq. NaOH  CCl4

*67. In the reaction,
The intermediate(s) is(are) :
(A) (B) (C) (D)
68. In the reaction the products are :
(A) (B)
(C) (D)
(A) an ether (B) an acetal

(C) an acid (D) a carbonyl compound
*70. In the following reaction, the product(s) formed is(are) :
(A) P (major) (B) Q (minor) (C) R (minor) (D) S (major)

71. The compound that does not liberate CO2 , on treatment with aqueous sodium bicarbonate solution is :
(A) benzoic acid
(B) benzensulphonic acid
(C) salicylic acid
(D) carbolic acid (phenol)

72. The major product(s) of the following reaction is (are) :
(A) P (B) Q (C) R (D) S

73. The acidic hydrolysis of ether (X) shown below is fastest when :
(A) One phenyl group is replaced by a methyl group

(B) One phenyl group is replaced by a para-methoxyphenyl group
(C) Two phenyl groups are replaced by two para-methoxyphenyl groups
(D) No structural change is made to X
74. For the identification of  -naphthol using dye test, it is necessary to use :
(A) dichloromethane solution of  -naphthol
(B) acidic solution of  -naphthol
(C) neutral solution of  -naphthol
(D) alkaline solution of  -naphthol
75. In the following reaction sequence, the correct structure(s) of X is (are) :
(A) (B) (C) (D)

76. Consider the following transformations of a compound P.
Choose the correct option(s).
(A) P is (B) X is Pd-C/quinoline/H2
(C) P is (D) R is
77. The reagent with which both acetaldehyde and acetone react easily is :
(A) Tollen’s reagent (B) Schiff’s reagent
(C) Grignard’s reagent (D) Fehling’s reagent
78. Which of the following has the most acidic hydrogen?

(A) 3-hexanone (B) 2, 4-hexanedione
(C) 2, 5-hexanedione (D) 2, 3-hexanedione
79. The order of reactivity of phenyl magnesium bromide with the following compounds is :
(A) (II) > (III) > (I) (B) (I) > (III) > (II)
(C) (II) > (I) > (III) (D) All of these
80. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E
on further treatment with aqueous KOH yields compound F. Compound F is :
(A) (B) (C) (D)
 OH
81.  PhCH2OH  PhCO2 the slowest step is :
In the Cannizzaro reaction given below, 2PhCHO 
(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 PhCH2OH

82. A compound A with molecular formula C10H13Cl gives a white precipitate on adding silver nitrate
solution. A on reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis gives
C and D. C gives Cannizzoro's reaction but not aldol condensation. D gives aldol condensation but not
Cannizzoro's reaction. A is :
(A) (B) C6H5  CH2  CH2  CH  CH3

|
Cl
(C) C6H5  CH2  CH2  CH2  CH2  Cl (D)
OH 
83. In the reaction 2CH3CHO   B; the product B is :
 A 
(A) CH3  CH2  CH2  CH2  OH (B) CH3  CH  CH  CHO

O
||
(C) CH3  C  CH3 (D) CH3  CH2  CH2  CH3
4 2 2 KMnO SOCl H /Pd

84. In the following sequence of reactions Toluene   A  B  C , the product C

BaSO4
is:
(A) C6H5COOH (B) C6H5CH3
(C) C6H5CH2OH (D) C6H5CHO
85. The major product obtained in the following reaction is :
(A) (B) (C) (D)
86. The correct sequence of reagents for the following conversion will be :

(A) 
 Ag NH
 3 2  OH , CH3MgBr, H  / CH3OH

(B) 
 Ag NH
3 2  OH , H  / CH3OH, CH3MgBr


(C) CH3MgBr, H / CH3OH,  Ag NH3  2  OH 


(D) CH3MgBr,  Ag NH3  2  OH  , H  / CH3OH


(A) (B) (C) (D)
88. The major product ‘Y’ in the following reaction is:
(A) (B) (C) (D)
89. Compound A(C9H10O) shows positive iodoform test. Oxidation of A with KMnO4 / KOH gives acid
B(C8H6O4 ) . Anhydride of B is used for the preparation of phenolphthalein. Compound A is:
(A) (B)
(C) (D)
HCl
90. 

In the following reaction, carbonyl compound  MeOH 
 acetal. Rate of the reaction is the highest
for:
(A) Acetone as substrate and methanol in excess
(B) Propanal as substrate and methanol in excess
(C) Propanal as substrate and methanol in stoichiometric amount
(D) Acetone as substrate and methanol in stoichiometric amount
91. Which of the following compounds will show the maximum ‘enol’ content?
(A) CH3COCH2COCH3 (B) CH3COCH2CONH2
(C) CH3COCH2COOC2H5 (D) CH3COCH3

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

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

94. The major product formed in the following reaction is :
(A) (B)
(C) (D)
95. The tests performed on compound X and their inference are :

Test Inference
(a) 2, 4-DNP test Coloured precipitate
(b) Iodoform test Yellow precipitate
(c) Azo-dye test No dye formation
Compound 'X' is :
(A) (B) (C) (D)

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

(A) (B)
(C) (D)
(A) (B) (C) (D)
99. In the following reactions, products A and B are :
(A) (B)
(C)
(D)

100. The aldehydes which will not form Grignard product with one equivalent Grignard reagents are :
(A) (B) (C) (D)

(A) (C), (D) (B) (B), (C), (D) (C) (B), (C) (D) (B), (D)
101. The major product in the following conversion is:
(A) (B)
(C) (D)
(i) Ni/H
2

(ii) DIBAL H
(A) (B)
(C) (D)
103. The major products of the following reactions are:
(A) (B)
(C) (D)

104. An unsaturated hydrocarbon X absorbs two hydrogen molecules on catalytic hydrogenation, and also
3 O 3 2 [Ag(NH ) ]
gives following reaction X  A   B(3-oxo-hexanedicarboxylic acid) X will be:

Zn/H2O
(A) (B) (C) (D)
105. In the following reaction A is :
(A) (B) (C) (D)
106. The increasing order of the reactivity of the following compounds in nucleophilic addition reaction is :
Propanal, Benzaldehyde, Propanone, Butanone
(A) Benzaldehyde < Butanone < Propanone < Propanal
(B) Propanal < Propanone < Butanone < Benzaldehyde
(C) Benzaldehyde < Propanal < Propanone < Butanone
(D) Butanone < Propanone < Benzaldehyde < Propanal
107. The compound A in the following reactions is:

(i) CH MgBr/H O
3 2 
A 
(ii) Conc. H SO / 
2 4
(i) O3
B 
(ii) Zn/H2O
C  D
O O
|| ||
(A) C6 H5  CH 2  C  CH3 (B) C6 H5  C  CH 2CH3
O
||
(C) (D) C6 H 5  C  CH3
108. Which of the following derivatives of alcohols is unstable in a aqueous base?
(A) (B) (C) RO  CMe3 (D)

109. The major product [C] of the following reaction sequence will be:
(A) (B)
(C) (D)
110. The increasing order of the following compounds towards HCN addition is:
(A) (i) < (iii) < (iv) < (ii) (B) (iii) < (iv) < (i) < (ii)
(C) (iii) < (iv) < (ii) < (i) (D) (iii) < (i) < (iv) < (ii)
111. The correct match between Item-I (starting material) and Item-II (reagent) for the preparation of
benzaldehyde is:
Item-I Item-II
(I) Benzene (P) HCl and SnCl 2, H3O 
(II) Benzonitrile (Q) H2, Pd-BaSO4 , S and quinoline
(III) Benzoyl chloride (R) CO, HCl and AlCl3

(A) (I)-(P), (II)-(Q) and (III)-(R) (B) (I)-(Q), (II)-(R) and (III)-(P)
(C) (I)-(R), (II)-(P) and (III)-(Q) (D) (I)-(R), (II)-(Q) and (III)-(P)
112. Which of the following compounds will give a yellow precipitate with iodine and alkali ?
(A) 2-hydroxy propane (B) Acetophenone
(C) Methyl acetate (D) Acetamide
113. Base catalysed aldol condensation occurs with :

(A) propionaldehyde (B) benzaldehyde
(C) 2-methyl propionaldehyde (D) 2, 2-dimethyl propionaldehyde

114. Show with balanced equation, what happens, when the following are mixed :
“Chloral is heated with aqueous hydroxide”
115. Write down the reactions involved in the preparation of the following using the reagents indicated against
in parenthesis :
“Acetoxime from acetaldehyde.” [K 2Cr 2O7 / H  , Ca (OH)2 and NH 2OH, HCl]
116. Outline the reaction sequence for the conversion of “acetylene to acetone”.
117. Give reason in one or two sentences for the following:

“Hydrazones of aldehydes and ketones are not prepared in highly acidic medium”.
118. Answer the followings with suitable equations wherever necessary.
(i) Suggest a reagent to distinguish acetaldehyde from acetone.
(ii) What happens when excess chlorine is passed through boiling toluene in the presence of
sunlight?
119. Fehling’s solution A consists of an aqueous solution of copper sulphate, while Fehling’s solution B
consists of an alkaline solution _______________.
120. Give reason in one or two sentences :

“Iodoform is obtained by the reaction of acetone with hypoiodite but not with iodide”.
121. In the following reactions, identify the compounds A, B, C and D.

(i) PCl5  SO2  A  B
(ii) A  CH 3COOH  C  SO 2  HCl
(iii) 2C  (CH3 )2 Cd  2D  CdCl 2
122. Acetophenone on reaction with hydroxylamine hydrochloride can produce two isomeric oximes. Write
structures of the oxime.
123. Complete the following, giving the structures of the principal organic products,
(i) (ii) ClCH2CH2CH2COPh  KOH  MeOH  B

D
(iii) (iv)
124. How many asymmetric carbon atoms are created during the complete reduction of benzil in
(PhCO  COPh) with LiAlH4 ? Also write the number of possible stereoisomers in the product.
125. In a Cannizzaro reaction, the intermediate that will be the best hydride donor is:
(A) (B) (C) (D)

126. Write the intermediate steps for each of the following reactions
3 H O
(i) C6H5CH(OH)C  CH  C6H5CH  CHCHO
(ii)
127. An aldehyde A (C11H8O), which does not undergo self aldol condensation, gives benzaldehyde and two
moles of B on ozonolysis. Compound B, on oxidation with silver ion gives oxalic acid. Identify the
compounds A and B.
*128. A new carbon-carbon bond formation is possible in :
(A) Cannizzaro’s reaction (B) Friedel-Crafts’ reaction
(C) Clemmensen’s reduction (D) Reimer-Tiemann reaction
129. The enol form of acetone, after treatment with D2O, gives :
OD O
| ||
(A) H3C  C  CH2 (B) D3C  C  CD3
OH OD
| |
(C) H2C  C  CH2D (D) D2C  C  CD3
130. (a) Compound A (C8H8O) on treatment with NH2OH. HCl gives B and C. B and C rearrange to give D
and E, respectively, on treatment with acid. B, C, D and E are all isomers of molecular formula
(C6 H9 NO). When D is boiled with alcoholic KOH, an oil F (C6H7 N) separates out. F reacts
rapidly with CH3COCl to give back D. On the other hand, E on boiling with alkali followed by
acidification gives a white solid G (C7H6O2 ). G Identify A-G.
(b) Carry out the following transformation in not more than three steps. 1-butyne  2-pentanone
131. The appropriate reagent for the following transformation :
(A) Zn(Hg), HCl (B) NH2NH2, OH  (C) H2 / Ni (D) NaBH4
132. Identify A, B and C, and give their structures.
133. An organic compound A, C6H10O, on reaction with CH3MgBr followed by acid treatment gives
compound B. The compound B on ozonolysis gives compound C, which in presence of a base gives
1-acetylcyclopentene D. The compound B on reaction with HBr gives compound E. Write the structures
of A, B, C and E. Show, how D is formed from C.

134. What would be the major product in the following reaction ?
135. Identify (A), (B) (C), (D) and (E) in the following schemes and write their structures
2 4Br /CCl 2 NaNH4 2 4 HgSO /H SO

2 2 NH NHCONH
 (A) (B)  (C) (D)
NaOD/D O(excess)
2
[C] (E)
HCl
136. (A ), C6H12 (B), C6 H13Cl  (C), C6H13Cl
Alcoholic KOH
(B)  (D), (an isomer of (A))
Ozonolysis
 (E) , (positive iodoform and negative Fehling’s solution test)
(D) 
Ozonolysis
(F)  (G) , (positive Tollen’s test for both)
(A ) 
Conc. NaOH
 HCOONa  A primary alcohol
(F)  (G) 
Identify the compounds(A) to (G)
137. A compound C9H7O2Cl exists predominantly in enol form (A) and also in keto form (B). On
oxidation with KMnO4 it gives m-chlorobenzoic acid as one of the products. Identify the compounds
(A) and (B).
138. In the following reaction sequence, the correct structures of E, F and G are :
(* implies 13C labeled carbon)
(A)
(B)
(C)
(D)
139. The smallest ketone and its next homologue are reacted with NH2OH to form oxime.
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active

140.
What is X ?
(A) CH3COOH (B) BrCH2COOH
(C) (CH3CO)2 O (D) HOC  COOH
141. 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
(A) (p) Nucleophilic substitution
(B) (q) Elimination
(C) (r) Nucleophilic addition
(D) (s) Esterification with acetic anhydride
(t) Dehydrogenation
Paragraph for Questions 142 - 144

A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by
dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes
intramolecular aldol reaction to give predominantly S.
142. The structure of the carbonyl compound P, is :
(A) (B) (C) (D)

143. The structure of the products Q and R, respectively, are :
(A) (B)
(C) (D)
144. The structure of the product S, is :
(A) (B) (C) (D)
Paragraph for Questions 145 – 147

Two aliphatic aldehydes P and Q react in the presence of aqueous K 2CO3 to give compound R, which upon
treatment with HCN provides compound S. On acidification and heating, S gives the product shown below :
145. The compounds P and Q respectively are :
(A) (B)
(C) (D)
146. The compound R is :
(A) (B) (C) (D)

147. The compound S is :
(A) (B) (C) (D)

An acyclic hydrocarbon P, having molecular formula C6H10 gave acetone as the only organic product through the
following sequence of reactions, in which Q is an intermediate organic compound.
148. The structure of compound P is :

(A) CH3CH2CH2CH2  C  CH
(B) H3CCH2  C  C  CH2CH3
(C)
(D)
149. The structure of the compound Q is :
(A) (B)
OH
|
CH3CH2CH2 C HCH2CH3
(C) (D)

150. Match the reactions in Column I with appropriate types of steps/reactive intermediate involved in these
reactions as given in Column II.
Column I Column - II
(A) (p) Nucleophilic substitution
(B) (q) Electrophilic substitution
(C) (r) Dehydration
(D) (s) Nucleophilic addition
(t) Carbanion

(CH CO) O
3 2 2 (i) H ,Pd/C
In the following reaction sequence, the compound J is an intermediate. I  J K
CH3COONa (ii) SOCl2
(iii) anhyd. AlCl 3
J (C9H8O2 ) gives effervescence on treatment with NaHCO3 and a positive Baeyer’s test.
151. The compound I is :
(A) (B) (C) (D)
152. The compound K is :
(A) (B)
(C) (D)

*153. Among P, Q, R and S, the aromatic compound(s) is(are) :
(A) P (B) Q (C) R (D) S
154. The major product H in the given reaction sequence is :

CN  2 4 95%H SO
CH3  CH2  CO  CH3 
 G  H


(A) CH3  CH  C  COOH (B) CH3  CH  C  CN
| |
CH3 CH3
OH
|
(C) CH3  CH2  C  COOH (D) CH3  CH  C  CO  NH2
| |
CH3 CH3
155. The number of aldol reaction(s) that occurs in the given transformation is :
(A) 1 (B) 2 (C) 3 (D) 4
156. The product of acid hydrolysis of P and Q can be distinguished by :

(A) Lucas reagent
(B) 2, 4-DNP
(C) Fehling’s solution
(D) NaHSO3
157. After completion of the reactions (I and II), the origin compound(s) in the reaction mixtures is(are):
(A) Reaction I : P and reaction II : P

(B) Reaction I : U, acetone and reaction II : Q, acetone
(C) Reaction I : T, U, acetone and reaction II : P
(D) Reaction I : R, acetone and reaction II : S, acetone

158. The major product in the following reaction is :
(A) (B)
(C) (D)

Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major products
formed in each step for both the schemes.
159. The product X is :
(A) (B)
(C) (D)
160. The correct statement with respect to product Y is :

(A) It gives a positive Tollens test and is a functional isomer of X
(B) It gives a positive Tollens test and is a geometrical isomer of X
(C) It gives a positive iodoform test and is a functional isomer of X
(D) It gives a positive iodoform test and is a geometrical isomer of X
161. Consider all possible isomeric ketones including stereoisomers of MW = 100. All these isomers are
independently reacted with NaBH4 . The total number of ketones that gives a racemic product(s)
is(are)_____________.

*162. Among the following, the number of reaction(s) that produce(s) benzaldehyde is ____________.
(A) (B)
(C) (D)
163. The correct statement about the synthesis of erythritol (C(CH2OH)4 ) used in the preparation of PETN is :
(A) The synthesis requires four aldol condensations between methanol and ethanol
(B) The synthesis requires two aldol condensations and two Cannizzaro reactions
(C) The synthesis requires three aldol condensations and one Cannizzaro reaction
(D) Alpha hydrogens of ethanol and methanol are involved in this reaction
164. The major product of the following reaction sequence is :
(A) (B) (C) (D)
*165. Positive Tollen’s test is observed for :
(A) (B) (C) (D)
166. A compound of molecular formula C8H8O2 reacts with acetophenone to form a single cross-aldol product
in the presence of base. The same compound on reaction with conc. NaOH forms benzyl alcohol as one of
the products. The structure of the compound is :
(A) (B) (C) (D)
167. Which of the following compounds will show highest dipole moment ?
I. II. III. IV.
(A) I (B) II (C) III (D) IV

*168. Compounds P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q and S is
C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S undergoes haloform
reaction but not Cannizzaro reaction.
1. O /CH Cl
3 2 2  1. O / CH Cl
3 2 2 
I. P  Q II. R  S
2. Zn /H2O (C8 H8 O) 2. Zn / H2O (C8 H8O)
The option(s) with suitable combination of P and R, respectively, is(are) :
(A) (B)
(C) (D)
*169. The reaction(s) leading to the formation of 1, 3, 5-trimethylbenzene is(are) :
(A) (B)
(C) (D)

Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3 / CuCl followed by reaction with
Ac 2O / NaOAc gives compound X as the major product. Compound X upon reaction with Br2 / Na 2CO3 , followed
by heating 473 K with moist KOH furnishes Y as the major product. Reaction of X with H2 / Pd-C, followed by
H3PO4 treatment produce Z as the major product.
170. The compound Y is :
(A) (B) (C) (D)

171. The compound Z is :
(A) (B) (C) (D)

172. This desired product X can be prepared by reacting the major product of the reactions in List-I with one
or more appropriate reagents in List-II. (Given, order of migratory aptitude : aryl > alkyl > hydrogen)
List-I List-II
(P) 1. I2 , NaOH
(Q) 2. [Ag (NH3 )2 ]OH
(R) 3. Fehling solution
(S) 4. HCHO, NaOH
5. NaOBr
The correct option is :

P Q R S P Q R S
(A) 1 2, 3 1 2, 4 (B) 1 3, 4 4, 5 3
(C) 1, 5 3, 4 5 2, 4 (D) 1, 5 2, 3 1, 5 2, 3

173. List-I includes starting materials and reagents of selected chemical reactions. List-II gives structures of
compounds that may be formed as intermediate products and/or final products from the reactions of
List-I.
List-I List-II
(I) (P)
(II) (Q)
(III) (R)
(IV) (S)
(T)
(U)
Which of the following options has the correct combination considering List-I and List-II?
(A) (II), (P), (S), (T) (B) (I), (S), (Q), (R) (C) (I), (Q), (T), (U) (D) (II), (P), (S), (U)

174. Choose the correct option(s) for the following reaction sequence
Consider Q, R and S as major products
(A)
(B)
(C)
(D)
175. Schemes 1 and 2 describe the conversion of P to Q and R to S, respectively. Scheme 3 describes the
synthesis of T from Q and S. The total number of Br atoms in a molecule of T is _______
Scheme 1 :
Scheme 2 :
Scheme 3 :

176. A compound with molecular mass 180 is acylated with CH3COCl to get a compound with molecular
mass 390. The number of amino groups present per molecule of the former compound is :
(A) 2 (B) 5 (C) 4 (D) 6
177. In the presence of small amount of phosphorous, aliphatic carboxylic acids react with chlorine or
bromine to yield a compound in which  -hydrogen has been replaced by halogen. This reaction is
known as :
(A) Wolff - Kishner reaction (B) Etard reaction
(C) Hell - Volhard - Zelinsky reaction (D) Rosenmund reaction
178. Bouveault-Blanc reduction reaction involves :

(A) Reduction of an acyl halide with H 2 / Pd
(B) Reduction of an ester with Na / C2H5OH
(C) Reduction of a carbonyl compound with Na/Hg and HCl
(D) Reduction of an anhydride with LiAlH4
179. The major product expected from the following reaction is:
(A) (B) (C) (D)

(A) (B) (C) (D)
181. The decreasing order of ease of alkaline hydrolysis for the following esters is :
(A) IV > II > III > I (B) III > II > IV > I
(C) II > III > I > IV (D) III > II > I > IV

182. An aromatic compound ‘A’ having molecular formula C7H 6O 2 on treating with aqueous ammonia and
heating forms compound ‘B’ the compound ‘B’ on reaction with molecular bromine and potassium
hydroxide provides compound ‘C’ having molecular formula C6H7 N. The structure of ‘A’ is :
(A) (B) (C) (D)

(A) (B) (C) (D)
(A) (B) (C) (D)
185. Identify (A) in the following reaction sequence :
(A) (B) (C) (D)

186. What is the product of the following reaction?

(i) NaBH
4
Hex  3  ynal 

(ii) PBr3
(iii) Mg/ether
(iv) CO2 /H3O 
(A) (B)
(C) (D)
187. The most suitable reagent for the given conversion is :
(A) B2 H 6 (B) LiAlH4 (C) H2 / Pd (D) NaBH4
188. [P] on treatment with Br2 / FeBr3 in CCl4 produced a single isomers C8H7O2Br while heating [P] with
sodalime gave toluene. The compound [P] is:
(A) (B) (C) (D)
189. An organic compound (A) (molecular formula C6H12O2 ) was hydrolysed with dil. H2SO4 to give a
carboxylic acid (B) and an alcohol (C). `C gives white turbidity immediately when treated with anhydrous
ZnCl2 and conc. HCl. The organic compound (A) is :
(A) (B) (C) (D)
190. Arrange the following in order of their increasing ease of hydrolysis :

CH3COOC2H5 , CH3COCl, (CH3CO)2 O, CH3CONH2
191. How will you bring about the following conversion?

“Ethanoic acid to a mixture of methanoic acid and diphenyl ketone.”
192. Complete the following reaction with appropriate structure.
2 5 2 5 NaOC H in absolute C H OH
C6H5CHO  CH3COOC2H5 
heat
193. Complete the following, giving the structures of the principal organic products.
(i)
2 4 conc. H SO
(ii) (COOH)2  (CH2OH)2    B
3 H O
(iii) H3CCOCOC6H5  NaOH C

194. Identify all the products formed in the following reaction sequence and explain briefly the formation of
the products.
195. Write the structures of the products A and B.

O
|| 18
H3O
CH3  C  O C2H5  A B
196. (±) 2-phenylpropanoic acid on treatment with (+)-2-butanol gives (A) and (B). Deduce their structures and
also establish stereochemical relation between them.
197.
Identify A to D.
198. 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)

199. RCONH2 is converted into RNH2 by means of Hofmann’s bromamide degradation.
NaOH
In this reaction, PhCONHBr is formed from which this reaction has derived its name. Electron donating
group at phenyl activates the reaction. Hofmann’s degradation reaction is an intramolecular reaction.
What are the constituent amines formed when the mixture of (1) and (2) undergoes Hofmann’s
bromamide degradation?
(A)
(B)
(C)
(D)
200. Amongst the following, that total number of compounds soluble in aqueous NaOH is

*201. Identify the binary mixture(s) that can be separated into individual compounds, by differential extraction,
as shown in the given scheme.
(A) C6H5OH and C6 H5COOH (B) C6H5COOHand C6H5CH2OH
(C) C6H5CH2OH and C6H5OH (D) C6H5CH2OH and C6 H5CH2COOH
202. The compound that undergoes decarboxylation most readily under mild condition is :
(A) (B)
(C) (D)
203. The compound that does NOT liberate CO2 , on treatment with aqueous sodium bicarbonate solution, is
(A) Benzoic acid
(B) Benzenesulphonic acid
(C) Salicylic acid
(D) Carbolic acid (Phenol)
P and Q are isomeric dicarboxylic acid C4H4O4. Both decolorize Br2/H2O. On heating, P forms a cyclic anhydride.
Upon treatment with dilute alkaline KMnO4. P as well as Q could produce one or more than one from compounds
S, T and U given :
Choose the correct option for 1 and 2 :
204. Compounds formed from P and Q are, respectively :

(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S

205. In the following reaction sequence V and W are, respectively :
(A) (B)
(C) (D)
206. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each
pathway from Column I with an appropriate structure from Column II and select the correct answer
using the code given below the lists.
Column I Column II
P. Pathway P 1.
Q. Pathway Q 2.
R. Pathway R 3.
S. Pathways S 4.
Codes
P Q R S P Q R S
(A) 1 3 4 2 (B) 2 4 3 1
(C) 4 1 2 3 (D) 3 2 1 4

207. The correct order of acidity for the following compounds is :
I II III IV
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
208. Reagent(s) which can be used to bring about the following transformation is(are)
(A) LiAlH4 ,in (C2H5 )2 O (B) BH3 in THF
(C) NaBH4 in C2H5OH (D) Raney Ni / H2 in THF
Paragraph for Questions 209-110

An organic acid P(C11H12O2 ) can easily be oxidized to a dibasic acid which reacts with ethylene glycol to produce
a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following
reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S.
1)H2 /Pd  C
2) NH3 /  1) H2 /Pd C 1) HCl
3) Br2 /NaOH
2 22)SOCl 2) Mg/Et O
S 
 P  Q R
4 )CHCl3 ,KOH, 3) MeMgBr,CdCl2 3)CO2 (dry ice)
5)H2 /Pd  C 4 ) NaBH4 4) H3O
209. The compound R is
(A) (B)
(C) (D)
210. The compound S is
(A) (B) (C) (D)

211. The correct order of acid strength of the following carboxylic acids is :
(A) I > III > II > IV (B) II > I > IV > III
(C) III > II > I > IV (D) I > II > III > IV
212. Ethyl isocyanide on hydrolysis in acidic medium generates :

(A) Ethanoic acid and ammonium salt (B) methylamine salt and ethanoic acid
(C) Ethylamine salt and methanoic acid (D) Propanoic acid and ammonium salt
213.
The alkene formed as a major product in the above elimination reaction is:
(A) (B) CH2  CH2 (C) (D)
214. A compound with molecular mass 180 is acylated with CH3COCl to get a compound with molecular
mass 390. The number of amino groups present per molecule of the former compound is
(A) 6 (B) 2 (C) 5 (D) 4
215. Considering the basic strength of amines in aqueous solution, which one has the smallest pK b value ?
(A) (CH3 )2 NH (B) CH3 NH2 (C) (CH3 )3 N (D) C6H5NH2
216. The increasing order of reactivity of the following compounds towards reaction with alkyl halides directly
is :
(A) (B) (C) (D)
(A) (A) < (B) < (C) < (D) (B) (A) < (C) < (D) < (B)
(C) (B) < (A) < (D) < (C) (D) (B) < (A) < (C) < (D)

(i) NaNO / H
2

 

(ii) CrO3 / H
(iii) H2 SO4  conc., 
(A) (B) (C) (D)

218. 
Ethylamine C2H5NH2  can be obtained from N-ethylphtahlimide on treatment with:
(A) NH2NH2 (B) NaBH4 (C) H2O (D) CaH2
219. Benzene diazonium chloride on reaction with aniline in the presence of dilute hydrochloric acid gives :
(A) (B)
(C) (D)
(A) (B)
(C) (D)
221. The major product obtained in the following reaction is:
(A) (B) (C) (D)

OH
| ethyl formate 1equiv.
CH3CHCH2CH2NH2  
triethylam in e
OH OH
| |
(A) CH3 CH CH2CH2NHCHO (B) CH3  CH  CH  CH2
(C) CH3CH  CH  CH2 NH2 (D)

223. Aniline dissolved in dilute HCL is reacted with sodium nitrate at 0C . This solution was added dropwise
to a solution containing equimolar mixture of aniline and phenol in dil. HCl. The structure of the major
product is :
(A) (B)
(C) (D)
224. Coupling of benzene diazonium chloride with 1-naphthol in alkaline medium will give :
(A) (B) (C) (D)

225. In the following reaction sequence,
the major product B is:
(A) (B)
(C) (D)

226. Consider the following reactions,
The compound [P] is:
(A) (B) (C) (D)
227. The major product Z obtained in the following reaction scheme is :
(A) (B)
(C) (D)
228. Consider the following reaction
OH 

'X'
The product ‘X’ is used:
(A) In laboratory test for phenols
(B) In acid base titration as an indicator
(C) As food grade colourant
(D) In protein estimation as an alternative to ninhydrin

229. Three isomers A, B and C (mol. formula C8H11N) give the following results:
R (product of A)
Diazotization (i) Hydrolysis
A and C  P  Q 
(ii) oxidation

S (product of C)
(KMnO 4  H  )
R has lower boiling point than S
C H SO Cl
6 5 2  alkali-insoluble product.
B 
A, B and C, respectively are:
(A)
(B)
(C)
(D)
230. The Kjeldahl method of Nitrogen estimation fails for which of the following reaction products ?
(a) (b)
(c) (d)
(A) (b) and (c) (B) (a) and (d) (C) (a), (c) and (d) (D) (c) and (d)
231. The final major product of the following reaction is:
(A) (B) (C) (D)

232. In the following reaction sequence, [C] is:
(A) (B)
(C) (D)
233. Match the following :
Test/Method Reagent
(i) Lucas Test (a) C6H5SO2Cl / aq.KOH
(ii) Dumas method (b) HNO3 / AgNO3
(iii) Kjeldahl’s method (c) CuO / CO2
(iv) Hinsberg Test (d) Conc. HCl and ZnCl2
(e) H2SO4
(A) (i)-(b), (ii)-(d), (iii)-(e), (iv)-(a) (B) (i)-(d), (ii)-(c), (iii)-(e), (iv)-(a)
(C) (i)-(d), (ii)-(c), (iii)-(b), (iv)-(e) (D) (i)-(b), (ii)-(a), (iii)-(c), (iv)-(d)
*234. When nitrobenzene is treated with Br 2 in the presence of FeBr 3 , the major product formed is
m-bromonitrobenzene. Statements which are related to obtain the m-isomer, are :
(A) the electron density on meta carbon is more than that on ortho and para position
(B) the intermediate carbocation formed after initial attack of Br  at the meta position is less
destabilised
(C) loss of Aromaticity when Br+ attacks at the ortho and para positions and not at meta position
(D) easier loss of H+ to regain Aromaticity from meta position than from ortho and para positions
235. What would be the major product in the following reaction?
236. Write structures of the product A, B, C, D and E in the following scheme.
NaNO ,HCl
2
237. C5H13 N  Y (tertiary alcohol + other products) Find X and Y. Is Y optically active? Write
 N2
optically active
X
the intermediate steps.

238. Statement-I : Aniline on reaction with NaNO 2 / HCl at 0°C followed by coupling with
  naphthol gives a dark blue coloured precipitate.
Statement-II : The colour of the compound formed in the reaction of aniline with NaNO 2 / HCl at 0°C
followed by coupling with   naphthol is due to the extended conjugation.

(A) Statement-1 is True, Statement-2 is True and Statement-2 is a correct explanation for
Statement-1
(B) Statement-1 is True, Statement-2 is True and Statement-2 is NOT a correct explanation for
Statement-1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True
239. Match each of the compounds in Column I with its characteristic reactions(s) in Column II.
Column I Column II
(A) CH3CH2CH2CN (p) Reduction with Pd-C/H2
(B) CH3CH 2OCOCH3 (q) Reduction with SnCl2/HCl
Development of foul smell on treatment with

(C) CH3CH  CHCH2OH (r)
chloroform and alcoholic KOH
Reduction with di-isobutylaluminium hydride

(D) CH3CH2CH2CH2NH2 (s)
(DIBAL-H)
(t) Alkaline hydrolysis
240. Match the reactions in Column I with appropriate options in Column II.
Column I Column II
(A) (p) Racemic mixture
(B) (q) Addition reaction
(C) (r) Substitution reaction
(D) (s) Coupling reaction
Carbocation
(t)
intermediate

241. Amongst the compounds given, the one that would form a brilliant coloured dye on treatment with
NaNO2 in dil. HCl followed by addition of an alkaline solution of   naphthol is:
(A) (B) (C) (D)
242. In the reaction shown below, the major products formed is :
(A) (B)
(C) (D)
243. Match the four starting materials (P, Q, R, S) given in List I with the corresponding reaction schemes
(I, II, III, IV) provided in List II and select the correct answer using the code given below the lists :
List I List II
(P) 1 Scheme I
(i) KMnO4 ,HO  ,heat (ii) H  ,H2O
(iii) SOCl2 (iv) NH3
? 
 C7H6 N 2O3
(Q) 2 Scheme II
(i) Sn/HCl (ii) CH3COCl (iii) conc. H2SO4
(iv ) HNO3 (v) dil. H2SO4 ,heat (vi) HO
? 
 C6 H6 N 2O2
(R) 3 Scheme III

(i) red hot iron, 873 K (ii) fu min g HNO3 , H2SO4 ,heat
(iii) H S.NH (iv) NaNO , H SO (v) hydrolysis
2 3 2 2 4
? 
 C6H5NO3
(S) 4 Scheme IV
(i) conc. H2SO4 , 60C
(ii) conc. HNO3 ,conc.H2SO4 (iii) dil. H2SO4 ,heat
?  C6H5 NO4
P Q R S P Q R S
(A) 1 4 2 3 (B) 3 1 4 2
(C) 3 4 2 1 (D) 4 1 3 2

244. The major product of the reaction is :
(A) (B) (C) (D)

245. In the following reactions, the products S is :
(A) (B) (C) (D)

246. In the following reactions, the major product W is :
(A) (B) (C) (D)

Treatment of compound O with KMnO4/H+ gave P, which on heating with ammonia
gave Q. The compound Q on treatment with Br2/NaOH produced R. On strong heating,
Q gave S, which on further treatment with ethyl 2-bromopropanoate in the presence of
KOH followed by acidification, gave a compound T.
247. The compound R is :
(A) (B) (C) (D)
248. The compound T is :

(A) glycine (B) alanine (C) valine (D) serine
JEE Main (Archive) | DTS-3 52 Biomolecules & Polymers

249. The product(s) of the following reaction sequence is(are) :
(A) (B) (C) (D)
(A) (B)
(C) (D)
251. Aniline reacts with mixed acid (conc. HNO3 and conc. H2SO4 ) at 288 K to give P(51 %), Q(47 %) and R
(2%). The major product(s) of the following reaction sequence is(are) :
(A) (B) (C) (D)
252. In the following reaction sequence, the amount of D (in g) formed from 10 moles of acetophenone
is______________.
(Atomic weights in g mol 1 : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%) corresponding to the
product in each step is given in the parenthesis)

253. Schemes 1 and 2 describe the conversion of P to Q and R to S, respectively. Scheme 3 describes the
synthesis of T from Q and S. The total number of Br atoms in a molecule of T is ______________.
Scheme 1 :
Scheme 2 :
Scheme 3 :
254. Consider the reaction sequence from P to Q shown below. The overall yield of the major product Q from P
is 75%. What is the amount in grams of Q obtained from 9.3 mL of P? (Use density of P = 1.00 g mL1 ;
Molar mass of C = 12.0, H = 1.0, O = 16.0 and N = 14.0 g mol 1 )
255. Complete hydrolysis of cellulose gives :

(A) D-fructose (B) D-ribose (C) D-glucose (D) L-glucose
256. The two forms of D-glucopyranose obtained from the solution of D-glucose are called :
(A) Isomer (B) Anomer (C) Epimer (D) Enantiomer
257. Bakelite is obtained by the polymerization of:
(A) Phenol & Formaldehyde (B) Ethylene glycol and phthalic acid
(C) Urea & Formaldehyde (D) None of these
*258. The correct statement(s) about the following sugars X and Y is are:
(A) X is a reducing sugar and Y is a non-reducing sugar

(B) X is a non-reducing sugar and Y is a reducing sugar
(C) The glycosidic linkages in X and Y are  and  , respectively
(D) The glycosidic linkages in X and Y are  and  sin 1  , respectively

259. Cellulose upon acetylation with excess acetic anhydride/H2SO4 (catalytic) gives cellulose triacetate whose
structure is:
(A) (B)
(C) (D)
260. Complete hydrolysis of starch gives :

(A) glucose and fructose in equimolar amounts
(B) galactose and fructose in equimolar amounts
(C) glucose only
(D) glucose and galactose in equimolar amounts
261. The formation of which of the following polymer involves hydrolysis reaction?
(A) Terylene (B) Nylon 6 (C) Bakelite (D) Nylon 6, 6
262. The incorrect statement among the following is :
(A)  -D-glucose and  -D-glucose are anomers.
(B)  -D-glucose and  -D-glucose are enantiomers.
(C) Cellulose is a straight chain polysaccharide made up of only  -D-glucose units.
(D) The penta acetate of glucose does not react with hydroxyl amine.
263. Fructose and glucose can be distinguished by:

(A) Seliwanoff’s test (B) Benedict’s test
(C) Barfoed’s test (D) Fehling’s test
264. Which of the following compounds is a constituent of the polymer ?
(A) Ammonia (B) N-Methyl urea (C) Formaldehyde (D) Methylamine
265. Which of the following statements is not true about sucrose?

(A) It is also named as invert sugar
(B) On hydrolysis, it produces glucose and fructose
(C) It is a non reducing sugar
(D) The glycosidic linkage is present between C1 of  -glucose and C4 of   fructose

266. The correct match between Item-I and Item-II is:

Column I Column II
(a) High density polythene (I) Peroxide catalyst
Condensation at high temperature &

(b) Polyacrylonitrile (II)
Pressure
(c) Novolac (III) Ziegler-Natta Catalyst
(d) Nylon 6 (IV) Acid or base catalyst

(A) (a)  (III), (b)  (I), (c)  (IV), (d)  (II)
(B) (a)  (III), (b)  (I), (c)  (II), (d)  (IV)
(C) (a)  (IV), (b)  (II), (c)  (I), (d)  (III)
(D) (a)  (II), (b)  (IV), (c)  (I), (d)  (III)
267. Amylopectin is composed of:

(A)   D- glucose, C1  C4 and C1  C6 linkages
(B)   D -glucose, C1  C 4 and C2  C6 linkages
(C)   D  glucose, C1  C 4 and C2  C6 linkages
(D)   D  glucose, C1  C4 and C1  C6 linkages
268. Which of the following is a condensation polymer?

(A) Buna-S (B) Teflon
(C) Neoprene (D) Nylon 6,6
269. The correct name of the following polymer is :

(A) Polyisobutylene (B) Polytert-butylene
(C) Polyisobutane (D) Polyisoprene
270. Which of the given statements is INCORRECT about glycogen ?

(A) It is a straight chain polymer similar to amylose
(B) It is present in animal cells
(C) It is present in some yeast and fungi
(D) Only   linkages are present in the molecule
271. Which of the following is a thermosetting polymer?

(A) Bakelite (B) PVC
(C) Buna-N (D) Nylon 6
272. Glucose and Galactose are having identical configuration in all the positions except position.
(A) C–3 (B) C–2 (C) C–4 (D) C–5
273. Which of the following tests cannot be used for identifying amino acids ?
(A) Ninhydrin test (B) Biuret test
(C) Barfoed test (D) Xanthoproteic test

274. Major product of the following reaction is :
(A) (B)
(C) (D)
(A) (B)
(C) (D)
276. The polymer obtained form the following reactions is :

(i) NaNO / H O
2 3

(ii) polymerisation
(A) (B)
(C) (D)
VMC | Revision Assignment 225 Organic Chemistry-2 | JEE-2022

277. Poly-  -hydroxybutyrate-co-  -hydroxyvalerate(PHBV) is a copolymer of _________.
(A) 3-hydroxybutanoic acid and 4-hydroxypentanoic acid
(B) 2-hydroxybutanoic acid and 3-hydroxypentanoic acid
(C) 3-hydroxybutanoic acid and 3-hydroxypentanoic acid
(D) 3-hydroxybutanoic acid and 2-hydroxypentanoic acid
278. The homopolymer formed from 4-hydroxybutanoic acid is :
 O   O O 
 ||   || || 
(A)  C  CH2 2 C — O —
—  (B)  C  CH2 2 C — O —
— 
 n  n
 O   O 
 ||   || 
(C)  O C  CH2 3 — O —
—  (D)  C  CH 2 3 — O —
— 
n n
(A) (B) (C) (D)
280. Two monomers in maltose are:

(A)  -D-glucose and  -D-glucose (B)  -D-glucose and  -D-glucose
(C)  -D-glucose and  -D-Fructose (D)  -D-glucose and  -D-galactose
281. Preparation of Bakelite proceeds via reactions:
(A) Electrophilic substitution and dehydration
(B) Condensation and elimination
(C) Electrophilic addition and dehydration
(D) Nucleophilic addition and dehydration
282. Which polymer has ‘chiral’ monomer(s)?

(A) Nylon 6, 6 (B) Neoprene (C) PHBV (D) Buna-N
283. Which of the following statement is not true for glucose ?
(A) Glucose exists in two crystalline forms  and 
(B) Glucose gives Schiff's test for aldehyde
(C) The pentaacetate of glucose does not react with hydroxylamine to give oxime
(D) Glucose reacts with hydroxylamine to form oxime
284. The number of chiral carbons present in sucrose is __________ .
285. What are the functional groups present in the structure of maltose?
(A) Two acetals (B) One acetal and one hemiacetal
(C) One acetal and one ketal (D) One ketal and one hemiketal

286. Consider the following reactions:
dry HCl x eq of
(i) Glucose + ROH 
 Acetal  acetyl derivative
(CH3CO)2 O
2 Ni/H y eq.of
(ii) Glucose  A  acetyl derivative
(CH3CO)2 O
z eq  of
(iii) Glucose  acetyl derivative
(CH3CO)2 O
‘x’, ‘y’ and ‘z’ in these reactions are respectively.

(A) 4, 5 and 5 (B) 5, 6 and 5 (C) 5, 4 and 5 (D) 4, 6 and 5
287. Which one of the following statements is not true?
(A) Lactose contains α-glycosidic linkage between C1 of galactose and C4 of glucose.
(B) On acid hydrolysis, lactose gives one molecule of D(+)-glucose and one molecule of D(+)-
galactose.
(C)  
Lactose C11H22O11 is a disaccharide and it contains 8 hydroxyl groups.
(D) Lactose is a reducing sugar and it gives Fehling’s test.

288. Which one of the following polymers is not obtained by condensation polymerization?
(A) Buna-N (B) Nylon 6, 6 (C) Bakelite (D) Nylon 6
289. The correct match between Item-I and Item-II is :
Item-I Item-II
(a) Natural rubber (I) 1, 3-butadiene + styrene
(b) Neoprene (II) 1, 3-butadiene + acrylonitrile
(c) Buna-N (III) Chloroprene
(d) Buna-S (IV) Isoprene
(A) (a)-(IV), (b)-(III), (c)-(I), (d)-(II) (B) (a)-(IV), (b)-(III), (c)-(II), (d)-(I)
(C) (a)-(III), (b)-(IV), (c)-(I), (d)-(II) (D) (a)-(III), (b)-(IV), (c)-(II), (d)-(I)
290. The structure of D-glucose is as follows

CHO
H OH
HO H
H OH
H OH
OH
(i) Draw the structure of L-glucose.
(ii) Give the reactions of L-glucose with Tollen’s reagent
*291. For ‘invert sugar’, the correct statement(s) is(are) :

(Given: specific rotations of (+) –sucrose, (+) –maltose, L-(–)-glucose and L-(+)-fructose in aqueous solution
are +66°, + 140°, –52° and + 92°, respectively)
(A) ‘invert sugar’ is prepared by acid catalyzed hydrolysis of maltose
(B) ‘invert sugar’ is an equimolar mixture of D-(+)-glucose and D-(–)-fructose
(C) specific rotation of ‘invert sugar’ is  20
(D) on reaction with Br2 water, ‘invert sugar’ forms saccharic acid as one of the products

292. Statement-1 : Glucose gives a reddish-brown precipitate with Fehling’s solution.
Statement-2 : Reaction of glucose with Fehling’s solution give CuO and gluconic acid.
(A) Statement-I is correct; Statement-II is correct; Statement-II is a correct explanation of
Statement-I
(B) Statement-I is correct; Statement-II is correct; Statement-II is not the correct explanation of
Statement-I
(C) Statement-I is correct; Statement-II is incorrect
(D) Statement-I is incorrect; Statement-II is correct
293. The correct statement about the following disaccharide is :

(A) Ring (a) is pyranose with   glycosidic link
(B) Ring (a) is furanose with   glycosidic link
(C) Ring (b) is furanose with   glycosidic link
(D) Ring (b) is pyranose with   glycosidic link
*294. The correct functional group X and the reagent Y in the following schemes are :
(A) X  COOCH3 ; Y  H2 / Ni / Heat

(B) X  CONH 2, Y  H2 / Ni / Heat
(C) X  CONH2 ; Y  Br 2 / NaOH
(D) X  CN ; Y  H2 / Ni / Heat
295. The following carbohydrate is :
(A) a ketohexose (B) an aldohexose (C) an  -furanose (D) an  -pyranose
296. A decapeptide (Molecular weight 796) on complete hydrolysis gives glycine (Molecular weight 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_______________.
297. When the following aldohexose exist in its D-configuration, the CHO
|
total number of stereoisomers in its pyranose form, CH2
is___________. |
CHOH
|
CHOH
|
CHOH
|
CH2OH

298. The substituents R1 and R 2 for nine peptides are listed in the table given below. How many of these
peptides are positively charged at pH = 7.0 ?


H3 N  CH2  CO  NH  CH  CO  NH  CH  CO  NH  CH 2  COO 
| |
R1 R2
Peptide R1 R2
I H H
II H CH3
III CH2COOH H
IV CH2CONH2 (CH2)4NH2
V CH2CONH2 CH2CONH2
VI (CH2)4NH2 (CH2)4NH2
VII CH2COOH CH2CONH2
VIII CH2OH (CH2)4NH2
IX (CH2)4NH2 CH3
299. A tetrapeptide has  COOH group on alanine. This produces glycine (Gly), valine (Val), phenyl alanine
(Phe) and alanine (Ala), on complete hydrolysis. For this tetrapeptide, the number of possible sequence
(primary structures) with  NH 2 group attached to a chiral centre is____________.
300. The total number of distinct naturally occurring amino acids obtained by complete acidic hydrolysis of
the peptide shown below is :

301. The structure of D-(+)-glucose is :
The structure of L-(  )-glucose is :
(A) (B) (C) (D)
302. Consider the following sequence for aspartic acid :
The pI (isoelectric point) of aspartic acid is :

(A) 1.88 (B) 3.65 (C) 5.74 (D) 2.77
303. On complete hydrogenation, natural rubber produces :

(A) ethylene-propylene copolymer (B) vulcanised rubber
(C) polypropylene (D) polybutylene
304. The Fischer presentation of D-glucose is given below.
The correct structure(s) of  -L-glucopyranose is(are) :
(A) (B) (C) (D)

305. Which of the following statement(s) is(are) true?
(A) Hydrolysis of sucrose gives dextrorotatory glucose and laevorotatory fructose
(B) Oxidation of glucose with bromine water gives glutamic acid
(C) Monosaccharides cannot be hydrolysed to give polyhydroxy aldehydes and ketones
(D) The two six-membered cyclic hemiacetal forms of D-(+)-glucose are called anomers

306. Choose the correct option(s) from the following:
(A) Teflon is prepared by heating tetrafluoroethene in presence of a persulphate catalyst at high
pressure
(B) Nylon-6 has amide linkages
(C) Cellulose has only  -D-glucose units that are joined by glycosidic linkages
(D) Natural rubber is polyisoprene containing trans alkene units
307. The Fischer projection of D-erythrose is shown below.
D-Erythrose and its isomers are listed as P, Q, R and S in column-I.
Choose the correct relationship of P, Q, R and S with D-erythrose from
Column II.
Column-I Column-II
P 1. Diastereomer
Q 2. Identical
R 3. Enantiomer
(A) P2, Q3, R2, S2 (B) P3, Q1, R1, S2
(C) P2, Q1, R1, S3 (D) P2, Q3, R3, S1

Vidyamandir Classes
JEE Advanced-2022
Answers to Selected Question for Revision | Organic Chemistry-2
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
A B D C C D A D D B B A A C D
16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
C B B C C A C D C A B B A B C
31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
A B B B D D A A C D C B D 69 D
46. X : (C2H5)2O, Y : C2H5I, Z : C2H5OH 47. (A) 48. (D) 49. m-cresol (m-methylphenol)
50. Isobutane < n-butane < n-butylchloride < n-butanol 51. (B) 52. (B)
53. Due to formation of peroxide 54. X : HC  CCH2 CH2CH2OH 55. o-nitrophenol
56. m-benzenedisulphonic acid, m-dihydroxybenzene 57. (CH3)2C = CH2

58. A : HC  C  C(OH)(CH3 )CH2CH3 B : (C2H5)2C(OH)CH3 59. (C)
60. Because of less important contributing structures 61. (AD)
62 63 64 65 66 67 68 69 70 71 72 72 74 75 76
C B C C AC D B BD D B C D B BC
77 78 79 80 81 82 83 84 85 86 87 88 89 90 91
C B C A B A B D B B B B D B A
92 93 94 95 96 97 98 99 100 101 102 103 104 105 106
C D A D D B D A D D D C B B D
107 108 109 110 111 112 113
A A B D C AB AC

114. Cl3CCHO  NaOH 
 CHCl3  HCOONa
[o] CaO 2  NH OH
115. CH3CHO  CH3COOH 
(CH3COO)2 Ca 
 CH3COCH3 (CH3)2 C  NOH
H2O
2 HO [O] CaO 
116. HC  CH 
2 
    CH3COCH3
 
Hg ,H

117. NH2 NH3 is less nucleophilic 118. (i) Tollen’s reagent 119. Sodium potassium tartarate
120. Hypo iodite is oxidizing agent and iodoform formation involve oxidation reaction. Iodide is reducing agent.
121. A  SOCl2 : B  POCl3 : C  CH3COCl : D  CH3COCH3
122.

Vidyamandir Classes
123.
124. Two asymmetric carbon atoms. Three stereoisomers 125. (C) 126. (i) Through carbocationic
intermediate
127. A : C 6H5CH  CH  C  C  CHO B : OHC  COOH 128. (BD) 129. (B)
130. (a) A : C6H5 COCH3 B & C : C6H5 (CH3 )C  NOH D : CH3 CONHC6H5 E : C6H5CONHCH3
F : C6H5NH2 G : C6H5COOH
2 2 1. B H
3 1. CH MgBr [O]
(b) C2H5C  CH  
 

 
2. H2 O2 /HO 2. H3 O
131.
132. 133.
134.
135. A  (CH3 )3 CCH  CH2 B  CH3CH(Cl)C(CH3 )3 C  (CH3 )3 CCH(Cl)CH3
D  (CH3 )2 CC(CH3 )2 E  CH3COCH3 F  (CH3 )3 CCHO
G  HCHO
136. A  m  Cl  C 6H4  C(OH)  CH  CHO B  m  Cl  C6H4  COCH2CHO
137 138 139 140 141 142 143 144 145 146 147 148
D B C A-p, q, t ; B-p, s, t ; C-r, s ; D-p B A B 1 B A D D
149 150 151 152 153 154 155 156 157 158 159 160
B A-r, s, t ; B-p, s ; C-r, s ; D-q, r A C ABCD A C C C D A C
161 162 163 164 165 166 167 168 169 170 171 172 173 174 175
5 ABCD C A ABD A A AB ABD C A D D BD 4
176 177 178 179 180 181 182 183 184 185 186 187 188 189
B C B C B D C D A A B A C D
190. CH3CONH2  CH3COOC2H5  (CH3CO)2 O  CH3COCl
5 6 6 PCl 6 5 C H
2 4 3 1. C H MgBr H SO 1. O
191. CH3COOH         C6H5COC6H5  HCOOH
AlCl3 2. H2O H2O 2. H2O2
192. C6H5CH  CHCOOC2H5
193. (i) O  O2N  C 6H4  CH2  COCOOC2H5 (ii) (iii) C6H5C(CH3 )(OH)COOH
18
194. Reformatsky reaction 195. A : CH3COOH, B : C2H5 OH
196. Diastereomers
197. A : C6H5CH2CN, B: C6H5CH(CN)CH(OH)C 6H5 , C : HOOC(C6H5 )C  CHC6H5 , D : CH3NHCO(C6H5 )C  CHC6H5

Vidyamandir Classes
198. (C) 199. (B) 200. (4) 201. (BD) 202. (B)
203. (D) 204. (B) 205. (A) 206. (A) 207. (A)
208. (C) 209. (A) 210. (B) 211. (D)
212 213 214 215 216 217 218 219 220 221 222 223 224 225 226
C B C A D A C B D A B A B B D
227 228 229 230 231 232 233 234
B A D A A D B AB
235.
236. A: B:
C: D: E:
237 238 239 240
X : CH(CH3 )2 CH(CH3 )NH2 ; Y : CH3CH2C(OH)(CH3 )2 D (A-q, s, t ; B-s, t ; C-p ; D-q) (A-r, s ; B-t ; C-p, q ; D-r)
241 242 243 244 245 246 247 248 249 250 251 252 253 254 255
C A C C A A A B B C D 495g 4 18.60 C
256 257 258 259 260 261 262 263 264 265 266 267 268 269 270
B A BC A C B B A C D A B D A A
271 272 273 274 275 276 277 278 279 280 281 282 283 284 285
A C C D B C C D B B A C B 9 B
286 287 288 289 290 291 292 293 294 295
D A A B (i) Mirror image of D-glucose; (ii) Gluconic acid BC C A ABCD B
296 297 298 299 300 301 302 303 304 305 306 307
6 8 4 4 1 A D A D ACD AB C

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Vidyamandir Classes: Innovating For Your Success

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

VMC | Revision Assignment 1 Organic Chemistry-II | JEE-2022

9. Consider the reaction sequence below :

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

10. The product of the reaction given below is :

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

11. In the following reaction sequence

12. The major product of the following reaction is :

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

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

VMC | Revision Assignment 2 Organic Chemistry-II | JEE-2022

15. The major product formed in the following reaction is :

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

16. The major product of the following reaction is :

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

(A) C4  O5 (B) O2  C3 (C) O5  C6 (D) C1  O2

(A) four (B) two (C) six (D) zero

VMC | Revision Assignment 3 Organic Chemistry-II | JEE-2022

20. The major product of the following reaction is :

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

(A) A = Benzyl chloride, B = Benzyl isocyanide

22. The major product of following reaction is :

(A) RCOOH (B) RCONH2 (C) RCHO (D) RCH2NH2

23. The major product of the following reaction is :

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

VMC | Revision Assignment 4 Organic Chemistry-II | JEE-2022

26. The major product of the following reaction is :

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

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

28. The major product of the following reaction is:

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

29. The major product of the following reaction is :

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

VMC | Revision Assignment 5 Organic Chemistry-II | JEE-2022

30. The major product of the following reaction is :

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

32. Consider the following reactions :

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

VMC | Revision Assignment 6 Organic Chemistry-II | JEE-2022

CH3  C  CH  CH2CH3 CH2  C  CH2  CH2CH3

37. Consider the following reaction:

VMC | Revision Assignment 7 Organic Chemistry-II | JEE-2022

40. The major product in the following reaction is:

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

VMC | Revision Assignment 8 Organic Chemistry-II | JEE-2022

Ceric ammonium nitrate test Positive Positive

Lucas Test Turbidity obtained after five Turbidity obtained immediately

Iodoform test Positive Negative

VMC | Revision Assignment 9 Organic Chemistry-II | JEE-2022

47. An industrial method of preparation of methanol is:

48. When phenol is treated with excess of bromine in water, it gives :

52. The product of combustion of an aliphatic thiol (RSH) at 298 K are :

56. Complete the following with appropriate structures :

VMC | Revision Assignment 10 Organic Chemistry-II | JEE-2022

I. II. III. IV.

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

The increasing order of boiling points of above mentioned alcohols is :

PARAGRAPH FOR QUESTIONS 64 - 66

Reimer-Tiemann reaction introduces an aldehyde