Top PYQ Organic Chemistry

Reactions of Alcohols
1. In the reaction given below ‘B’ is
2.
In the above reaction, left hand side and right hand side rings are named as ‘A’ and ‘B’
respectively. They undergo ring expansion. The correct statement for this process is:
A. Ring expansion can go up to seven membered rings

B. Finally both rings will become six membered each.
C. Finally both rings will become five membered each.
D. Only A will become 6 membered.
3. In the following reaction, ‘B’ is
4. Find out the major product for the following reaction
A. B.
C. D.
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Reactions of Phenol
5. A compound ' X ' when treated with phthalic anhydride in presence of concentrated H2SO4 yields
‘Y’. ‘Y’ is used as an acid/base indicator. 'X' and 'Y' are respectively
A. Anisole, methyl orange
B. Salicylaldehyde, Phenolphthalein
C. Toludine, Phenolphthalein
D. Carbolic acid, Phenolphthalein
Preparation of Ethers
6. ‘A’ in the given reaction is
A. B.
C. D.
Dihydric alcohols
7.
‘A’ formed in the above reaction is
A. B.
C. D.
Properties of Phenol
8. The increasing order of pK a for the following phenols is
(A) 2, 4-Dinitrophenol
(B) 4-Nitrophenol
(C) 2, 4, 5-Trimethylphenol
(D) Phenol
(E) 3-Chlorophenol
Choose the correct answer from the option given below:
A. (A), (E), (B), (D), (C)

B. (A), (B), (E), (D), (C)
C. (C), (D), (E), (B), (A)
D. (C), (E), (D), (B), (A)
Chirality
9. The total number of chiral compound/s from the following is
Conformations
10. Which of the following conformations will be the most stable?
(A)
(B)
(C)
(D)
Preparation of Alkyl Halides

11. In the following given reaction ‘A’ is
A.
B.
C.
D.
Reactions of Alkyl Halides

12. The one giving maximum number of isomeric alkenes on dehydrohalogenation reaction is
(excluding rearrangement)
A. 1-Bromo-2-methylbutane
B. 2-Bromopropane
C. 2-Bromopentane
D. 2-Bromo-3, 3-dimethylpentane
13. In the above conversion of compound (X) to product (Y), the sequence of reagents to be used
will be:
A. (𝑖)𝐵𝑟2 , 𝐹𝑒(𝑖𝑖)𝐹𝑒, 𝐻 + (𝑖𝑖𝑖)𝐿𝑖𝐴𝑙𝐻4
B. (𝑖)𝐵𝑟2 (𝑎𝑞)(𝑖𝑖)𝐿𝑖𝐴𝑙𝐻4 (𝑖𝑖𝑖)𝐻3 𝑂+
C. (𝑖)𝐹𝑒, 𝐻 + (𝑖𝑖)𝐵𝑟2 (𝑎𝑞)(𝑖𝑖𝑖)𝐻𝑁𝑂2 (𝑖𝑣)𝐶𝑢𝐵𝑟
D. (𝑖)𝐹𝑒, 𝐻 + (𝑖𝑖)𝐵𝑟2 (𝑎𝑞)(𝑖𝑖𝑖)𝐻𝑁𝑂2 (𝑖𝑣)𝐻3 𝑃𝑂2
14. The major product ‘P’ formed in the given reaction is
A.
B.
C.
D.
15. Identify the correct order for the given property for following compounds
A. Boiling Point:
B. Density:
C. Boiling Point:
D. Density:
E. Boiling Point:
Choose the correct answer from the option given below: -

A. (B), (C) and (D) only
B. (A), (C) and (E) only
C. (A), (C) and (D) only
D. (A), (B) and (E) only
16. Maximum number of isomeric monochloro derivatives which can be obtained from 2, 2, 5, and
5- tetramethyl hexane by chlorination is ____.
17. In the following halogenated organic compounds, the one with maximum number of chlorine
atoms in its structure is:
A. Chloral
B. Gammaxene
C. Chloropicrin
D. Freon-12
18. The correct order of melting of dichlorobenzenes is
A.
B.
C.
D.
19. The major product for the following reaction is :
A.
B.
C.
D.
SN1 and SN2 Reactions

20. 2-Methyl propyl bromide reacts with 𝐶2 𝐻5 𝑂− and gives ‘A’ whereas on reaction with 𝐶2 𝐻5 𝑂𝐻
it gives ‘B’. The mechanism followed in these reactions and the products ‘A’ and ‘B’ respectively
are:
A. 𝑆𝑁 2, 𝐴 = 𝑖𝑠𝑜 − 𝑏𝑢𝑡𝑦𝑙 𝑒𝑛𝑡ℎ𝑦𝑙 𝑒𝑡ℎ𝑒𝑟; 𝑆𝑁 1, 𝐵 = tert-butyl ethyl ether
B. 𝑆𝑁 1, 𝐴 = tert-butyl ethyl ether; 𝑆𝑁 1, 𝐵 = 2 −butyl ethyl ether
C. 𝑆𝑁 2, 𝐴 = 2-butyl ethyl ether; 𝑆𝑁 2, 𝐵 = iso-butyl ethyl ether
D. 𝑆𝑁 1, 𝐴 = tert-butyl ethyl ether; 𝑆𝑁 2, B = iso-butyl ethyl ether
21. For the reaction

𝑅𝐶𝐻2 𝐵𝑟 + 𝐼 − 𝐴𝑐𝑒𝑡𝑜𝑛𝑒 → 𝑅𝐶𝐻2 𝐼 + 𝐵𝑟 −
The correct statement is
A. 𝐵𝑟 − Can act as competing nucleophile.
B. The reaction can occur in acetic acid also.
C. The transition state formed in the above reaction is less polar than the localised anion.
D. The solvent used in the reaction solvates the ions formed in rate determining step
22. Choose the halogen which is most reactive towards SN1 reaction in the given compounds (A, B,
C & D)
A.
B.
C.
D.
A. 𝐴 − 𝐵𝑟(𝑏) ; 𝐵 − 𝐼(𝑎) ; 𝐶 − 𝐵𝑟(𝑎) ; 𝐷 − 𝐵𝑟(𝑎)

B. 𝐴 − 𝐵𝑟(𝑏); 𝐵 − 𝐼(𝑏) ; 𝐶 − 𝐵𝑟(𝑏); 𝐷 − 𝐵𝑟(𝑏)
C. 𝐴 − 𝐵𝑟(𝑎) ; 𝐵 − 𝐼(𝑎) ; 𝐶 − 𝐵𝑟(𝑏) ; 𝐷 − 𝐵𝑟(𝑎)
D. 𝐴 − 𝐵𝑟(𝑎) ; 𝐵 − 𝐼(𝑎) ; 𝐶 − 𝐵𝑟(𝑎) ; 𝐷 − 𝐵𝑟(𝑎)
23.
Where Nu = Nucleophile
Find out the correct statement from the options given below for the above two reactions.
A. Reaction (I) is of 2nd order and reaction (II) is of 1st order
B. Reactions (I) and (II) both are of 2nd order
C. Reactions (I) is of 1st order and reaction (II) is of 2 nd order
D. Reaction (I) and (II) both are of 1st order
Stability of Intermediates
24. Increasing order of stability of the resonance structure is:
(A) C,D,B,A
(B) C,A,B,D
(C) D,C,A,B
(D) D,C,B,A
Aromaticity
25. Given below are two statements :
Statement I: Tropolone is an aromatic compound and has 8π electrons.
Statement II: π electrons of >C=O group in tropolone is involved in aromaticity. In the light of
the above statements choose the correct answer from the options given below:
(A) Statement I is true but Statement II is false

(B) Statement I is false but Statement II is true
(C) Both Statement I and Statement II are false
(D) Both Statement I and Statement II are true
26. Correct statements for the given reaction are:
A. Compound ‘B ’ is aromatic
B. The completion of above reaction is very slow
C. ‘A ’ shows tautomerism
D. The bond lengths of C−C in compound B are found to be same
Choose the correct answer from the options given below.
(A) B, C and D only
(B) A, B and C only
(C) A, C and D only
(D) A, B and D only
Acidic Strength
27. The correct order of pKa values for the following compounds is:
(A) c > a > d > b

(B) b > d > a > c
(C) b > a > d > c
(D) a > b > c > d
28. What is the correct order of acidity of the protons marked A–D in the given compounds?
(A) HC>HD>HB>HA
(B) HC>HD>HA>HB
(C) HD>HC>HB>HA
(D) HC>HA>HD>HB
Reactions of Diaz onium Salts

29.
In the abo e conversion the correct sequence of reagents to be added is
A. (i) 𝐾𝑀𝑛 𝑂4 , (𝑖𝑖)𝐵𝑟2 /𝐹𝑒, (𝑖𝑖𝑖)𝐹𝑒/𝐻 + , (𝑖𝑣)𝐶𝑙2

B. (i) 𝐵𝑟2 /𝐹𝑒, (𝑖𝑖) 𝐹𝑒/𝐻 + , (𝑖𝑖𝑖) 𝐾𝑀𝑛𝑂4 , (𝑖𝑣)𝐶𝑙2
C. (i) 𝐹𝑒/𝐻 + , (𝑖𝑖)𝐻𝑂𝑁𝑂, (𝑖𝑖𝑖) 𝐶𝑢𝐶𝑙, (𝑖𝑣) 𝐾𝑀𝑛𝑂4 (𝑣)𝐵𝑟2
D. (i) 𝐵𝑟2 /𝐹𝑒, (𝑖𝑖)𝐹𝑒/𝐻 + , (𝑖𝑖𝑖) 𝐻𝑂𝑁𝑂, (𝑖𝑣) 𝐶𝑢𝐶𝑙 (𝑣) 𝐾𝑀𝑛 𝑂4
30. Consider the following sequence of reaction
The product ‘B’ is

A.
B.
C.
D.
𝐻𝑁𝑂2 ′𝑋′
31. O-Phenylenediamine → ‘X’
𝑀𝑎𝑗𝑜𝑟 𝑃𝑟𝑜𝑑𝑢𝑐𝑡
A.
B.
C.
D.
32. Choose the correct colour of the product for the following reaction.
A. Yellow
B. White
C. Red
D. Blue
Gabriel Phthalimidine Reaction

33. Number of isomeric aromatic amines with molecular formula 𝐶8 𝐻11 𝑁, which can be synthesized
by Gabriel Phthalimide synthesis is ___.
Hoffmann Bromoimide Degradation
34. The major product formed in the following reaction is
A.
B.
C.
D.
Reactions of Aniline
35.
Compound P is neutral, Q gives effervescence with 𝑁𝑎𝐻𝐶𝑂3 while R reacts with Hinsberg’s
reagent to give solid soluble in 𝑁𝑎𝑂𝐻. Compound P is
A.
B.
C.
D.
36. In the following reaction, ‘A’ is
‘A’ Major Product
A.
B.
C.
D.
37. How many of the transformation given below would result in aromatic amines?
1.
2.
3.
4.
38. Benzyl isocyanide can be obtained by:

A.
B.
C.
D.
Chooose the correct answer from the options given below:
A. A and D
B. Only B
C. A and B
D. B and C
Properties of Amines
39. Match List I with List II
List I (Amines) List II (pKb)
A. Aniline I. 3.25
B. Ethan amine II. 3.00
C. N-Ethylethanamine III. 9.38
D. N, N-Diethylethanamine IV. 3.29
Choose the correct answer from the options given below:-
A. A-I, B-IV, C-II, D-III
B. A-III, B-II, C-I, D-IV
C. A-III, B-II, C-IV, D-I
D. A-III, B-IV, C-II, D-I
40. An organic compound [𝐴](𝐶4 𝐻11 𝑁), shows optical activity and gives 𝑁2 gas on treatment with
𝐻𝑁𝑂2 . The compound [A] reacts with 𝑃ℎ𝑆𝑂2 Cl producing a compound which is soluble in KOH.
The structure of A is:
A.
B.
C.
D.
41.
A.
B.
C.
D.
42. The major products A and B from the following reactions are:
A.
B.
C.
D.
Method of preparation for both aldehydes and ketones

43. Cyclohexylamine when treated with nitrous acid yields (P). On treating (P) with PCC results in
(Q). When (Q) is heated with dil. NaOH we get (R) The final product (R) is:
A.
B.
C.
D.
𝑖) 𝐻𝐶𝑁
→
44. 𝐷 − (+) − 𝐺𝑙𝑦𝑐𝑒𝑟𝑎𝑙𝑑𝑒ℎ𝑦𝑑𝑒 𝑖𝑖) 𝐻 𝑂/𝐻 +
2
𝑖𝑖𝑖)𝐻𝑁𝑂3
The products formed in the above reaction are
A. One optically active and one meso product
B. Two optically inactive products
C. Two optically active products
D. One optically inactive and one meso product
45.
A in the above reaction is:
A.
B.
C.
D.
46.
The value of x in compound ‘D’ is ____.
47. Consider the following reaction

(𝑖)𝑑𝑖𝑙. 𝑁𝑎𝑂𝐻
→
(𝑖𝑖)∆ 𝑃𝑟𝑜𝑑𝑢𝑐𝑡 𝐵
Propanal + Methanal =
(𝐶5 𝐻8 𝑂3 )
(𝑖𝑖𝑖)𝑁𝑎𝐶𝑁
(𝑖𝑣)𝐻3 𝑂+
The correct statement for product B is. It is
A. Optically active and adds one mole of bromine
B. Racemic mixture and is neutral
C. Racemic mixture and gives a gas with saturated 𝑁𝑎𝐻𝐶𝑂3 solution
D. Optically active alcohol and is neutrall
48. Find out the major products from the following reaction sequence.
A.
B.
C.
D.
49. Compound (X) undergoes following sequence of reaction to give the Lactone (Y)
A.
B.
C.
D.
50. The mass of 𝑁𝐻3 produced when 131.8 kg of cyclohexane carbaldehyde undergoes Tollen’s test
is ____ Kg. (Nearest Integer)
Molar mass of C = 12 g/mol
N = 14 g/mol
O = 16 g/mol
51. Among the following the number of compounds which will give positive iodoform reaction is
___.
a. 1-Phenylbutan-2-one
b. 2-Methylbutan-2-ol
c. 3-Methylbutan-2-ol
d. 1-Phenylethanol
e. 3, 3-dimethylbutan-2-one
f. 1-Phenylpropan-2-ol
52. The number of molecules which given halo form test among the following molecules is:
53.
The correct sequence of reagents for the preparation of Q and R is:

A. (𝑖)𝐶𝑟2 𝑂3 , 770𝐾, ; (𝑖𝑖) 𝐶𝑟𝑂2 , 𝐻3 𝑂+ ; (𝑖𝑖𝑖)𝑁𝑎𝑂𝐻; (𝑖𝑣)𝐻3 𝑂+ 20 𝑎𝑡𝑚
B. (𝑖)𝐶𝑟𝑂2 𝐶𝑙2 , 𝐻3 𝑂+ ; (𝑖𝑖)𝐶𝑟2 𝑂3 , 770 𝐾, ; (𝑖𝑖𝑖)𝑁𝑎𝑂𝐻; (𝑖𝑣)𝐻3 𝑂+ 20 𝑎𝑡𝑚
C. (𝑖)𝐾𝑀𝑛𝑂4 , 𝑂𝐻 − ; (𝑖𝑖)𝑀𝑜2 𝑂3 , ∆; (𝑖𝑖𝑖)𝑁𝑎𝑂𝐻; (𝑖𝑣)𝐻3 𝑂+
D. (𝑖)𝑀𝑜2 𝑂3 , ∆; (𝑖𝑖)𝐶𝑟𝑂2 , 𝐶𝑙2 , 𝐻3 𝑂+ ; (𝑖𝑖𝑖)𝑁𝑎𝑂𝐻; (𝑖𝑣)𝐻3 𝑂+
54. The product formed in the following multistep reaction is:
CH3-CH=CH2 iB2H6 iiH2O2, NaOH → iiiPCC ivCH3MgBr
A.
B.
C.
D. 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝑂𝐻

55. The major products ‘A’ and ‘B’, respectively, are
A.
B.
C.
D.
56.
‘A’ and ‘B’ in the above reactions are:
A.
B.
C.
D.
57. Given below are two statements:
Statement I:
Under Clemmensen reduction conditions will give
Statement II:
Under Wolff-Kishner reduction condition will give
Under Wolff-Kishner reduction condition will give
In the light of the above statements, choose the correct answer from the options given below:
A. Statement I is false but Statement II is true
B. Both Statement I and Statement II are false
C. Statement I is true but Statement II is false
D. Both Statement I and Statement II are true
Reactions of Alkanes
58. Number of bromo derivatives obtained on treating ethane with excess of 𝐵𝑟2 in diffused
sunlight is
59. When 0.01 mol of an organic compound containing 60% carbon was burnt completely, 4.4 g of
𝐶𝑂2 was produced. The molar mass of compound is ___ 𝑔 𝑚𝑜𝑙 −1 (Nearest integer)
60. A hydrocarbon ‘X’ with formula 𝐶6 𝐻8 uses two moles of 𝐻2 on catalystic hydrogenation of its
one mole. On ozonolysis, ‘X’ yields two moles of methane dicarbaldehyde. The hydrocarbon ‘X’
is:
A. Hexa-1, 3, 5-triene
B. 1-methylcyclopenta-1, 4-diene
C. Cyclohexa-1, 3-diene
D. Cyclohexa-1, 4-diene
61. 17 mg of a hydrocarbon (M.F. 𝐶10 𝐻16) takes up 8.40 mL of the 𝐻2 gas measured at 0°C and 760
mm of Hg. Ozonolysis of the same hydrocarbon yields
The number of double bond/s present in the hydrocarbon is

62. The compound which will have the lowest rate towards nucleophilic aromatic substitution on
treatment with 𝑂𝐻 − is.
A.
B.
C.
D.
63. Arrange the following compounds in increasing order of rate of aromatic electrophilic
substitution reaction.
A. d, b, c, a
B. d, b, a, c
C. b, c, a, d
D. c, a, b, d
64. ‘X’ is:
A.
B.
C.
D.
65. Decreasing order of reactivity towards electrophilic substitution for the following compounds is:
A. d>a>e>c>b
B. >d>a>b>c
C. a>d>e>b>c
D. c>b>a>d>e
Structure of Glucose and Fructose

66. The correct representation in six membered pyranose form for the following sugar [X] is
A.
B.
C.
D.
67. Compound A,𝐶5 𝐻10 𝑂5 give a tetra acetate with 𝐴𝐶2 𝑂 and oxidation of A with 𝐵𝑟2 − 𝐻2 𝑂 gives
an acid,𝐶5 𝐻10 𝑂6 . Reduction of A with HI gives isopentane. The possible structure of A is:
AMINO ACIDS & PROTEINS
68. Following tetra peptide can be represented as
(F, L, D, Y, I, Q, P are one letter codes for amino acids)

A. FIQY
B. FLDY
C. YQLE
D. PLDY
69. Given below are two statements: one is labelled as Assertion (A) and the other is labelled as
Reason (R).
Assertion (A): Ketoses give Seliwanoff’s test faster than Aldoses.
Reason (R): Ketoses undergo 𝛽-elimination followed by formation of furfural.
In the light of the above statements, choose the correct answer from the options given below:
A. (A) if false but (R) is true
B. Both (A) and (R) are true and (R) is the correct explanation of (A)
C. (A) is true but (R) is false
D. Both (A) and (R) are true but (R) is not the correct explantion of (A)
70. Number of cyclic tripeptides formed with 2 amino acids A and B is:
A. 2
B. 3
C. 5
D. 4
71. A short peptide on complete hydrolysis produces 3 moles of glycine (G), two moles of leucine (L)
and two moles of valine (V) per mole of peptide. The number of peptide linkages in it are ____.
Answer Key.
1. D 26. C 51. 4
2. B 27. B 52. 3
3. C 28. B 53. A
4. B 29. D 54. C
5. D 30. C 55. A
6. B 31. A 56. B
7. A 32. C 57. C
8. B 33. 5 58. 9
9. 2 34. B 59. 200
10. A 35. D 60. D
11. D 36. B 61. 3
12. C 37. 3 62. D
13. D 38. C 63. D
14. A 39. D 64. A
15. B 40. D 65. B
16. 3 41. A 66. B
17. B 42. C 67. A
18. D 43. B 68. B
19. B 44. A 69. C
20. A 45. C 70. D
21. C 46. 15 71. 6
22. C 47. C
23. C 48. B
24. B 49. A
25. A 50. 60
Fill Your Answers
Q1 Q26 Q51
Q2 Q27 Q52
Q3 Q28 Q53
Q4 Q29 Q54
Q5 Q30 Q55
Q6 Q31 Q56
Q7 Q32 Q57
Q8 Q33 Q58
Q9 Q34 Q59
Q10 Q35 Q60
Q11 Q36 Q61
Q12 Q37 Q62
Q13 Q38 Q63
Q14 Q39 Q64
Q15 Q40 Q65
Q16 Q41 Q66
Q17 Q42 Q67
Q18 Q43 Q68
Q19 Q44 Q69
Q20 Q45 Q70
Q21 Q46 Q71
Q22 Q47
Q23 Q48
Q24 Q49
Q25 Q50

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Reactions of Alcohols

1. In the reaction given below ‘B’ is

A. Ring expansion can go up to seven membered rings

4. Find out the major product for the following reaction

‘A’ formed in the above reaction is

Choose the correct answer from the option given below:

A. (A), (E), (B), (D), (C)

Preparation of Alkyl Halides

Reactions of Alkyl Halides

14. The major product ‘P’ formed in the given reaction is

Choose the correct answer from the option given below: -

19. The major product for the following reaction is :

SN1 and SN2 Reactions

21. For the reaction

A. 𝐴 − 𝐵𝑟(𝑏) ; 𝐵 − 𝐼(𝑎) ; 𝐶 − 𝐵𝑟(𝑎) ; 𝐷 − 𝐵𝑟(𝑎)

Statement I: Tropolone is an aromatic compound and has 8π electrons.

(A) Statement I is true but Statement II is false

Choose the correct answer from the options given below.

(A) B, C and D only

(A) c > a > d > b

Reactions of Diaz onium Salts

A. (i) 𝐾𝑀𝑛 𝑂4 , (𝑖𝑖)𝐵𝑟2 /𝐹𝑒, (𝑖𝑖𝑖)𝐹𝑒/𝐻 + , (𝑖𝑣)𝐶𝑙2

The product ‘B’ is

Gabriel Phthalimidine Reaction

36. In the following reaction, ‘A’ is

38. Benzyl isocyanide can be obtained by:

Chooose the correct answer from the options given below:

Method of preparation for both aldehydes and ketones

A in the above reaction is:

The value of x in compound ‘D’ is ____.

47. Consider the following reaction

The correct sequence of reagents for the preparation of Q and R is:

D. 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻2 − 𝑂𝐻

‘A’ and ‘B’ in the above reactions are:

Under Clemmensen reduction conditions will give

Under Wolff-Kishner reduction condition will give

Under Wolff-Kishner reduction condition will give

The number of double bond/s present in the hydrocarbon is

64. ‘X’ is:

Structure of Glucose and Fructose

(F, L, D, Y, I, Q, P are one letter codes for amino acids)

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