Chaptewise PYQ 2023 Organic Chemistry

C H E M IS TR Y
JEE-MAIN 2023
ORGANIC CHEMISTRY CHAPTERWISE QUESTION BANK

GENERAL ORGANIC CHEMISTRY
1. Increasing order of stability of the resonance structure is :

OHC OHC
NH2 NH2
A. B.
+
H OHC NH2
NH2
C. D.
[24 Jan, Shift – 1 - 2023]
(1) C, D, B, A (2) C, D, A, B (3) D, C, A, B (4) D, C, B, A
2. Given below are two statements, one is labelled as Assertion A and the other is labelled
as Reason R. Assertion A: Benzene is more stable than hypothetical cyclohexatriene.
Reason R: The delocalized  electron cloud is attracted more strongly by nuclei of
carbon atoms.
In the light of the above statements, choose the correct answer from the options given
below: [24 Jan, Shift – 2 - 2023]
(1) A is true but R is false.
(2) A is false but R is true.
(3) Both A and R are correct and R is the correct explanation of A.
(4) Both A and R are correct but R is NOT the correct explanation of A.
3. Which will undergo deprotonation most readily in basic medium?
[24 Jan, Shift – 2 - 2023]
O O O O O O
MeO OMe OMe

a b c
(1) a only (2) c only (3) Both a and c (4) b only

4. The correct order in aqueous medium of basic strength in case of methyl substituted
amines is : [25 Jan, Shift – 1 - 2023]
(1) Me2NH>MeNH2>Me3N> NH (2) Me2NH>Me3N>MeNH2>NH3
(3) NH3>Me3N>MeNH2>Me2NH (4) Me3N>Me2NH>MeNH2>NH3
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5. Match List I with List II
List I (Amines) List II

A. Aniline I. 3.25
B. Ethanamine 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:- [25 Jan, Shift – 2 - 2023]
(1) A-I, B-IV, C-II, D-III (2) A-III, B-II, C-I, D-IV
(3) A-III, B-II, C-IV, D-I (4) A-III, B-IV, C-II, D-I
6. The increasing order of pKa for the following phenols is [29 Jan, Shift - 1 - 2023]
(1) 2, 4-Dinitrophenol (2) 4 - Nitrophenol
(3) 2, 4, 5- Trimethylphenol (4) Phenol
(5) 3-Chlorophenol
7. What is the correct order of acidity of the protons marked A–D in the given compounds?
HD CO2HC
HA
HB
[30 Jan, Shift - 1 - 2023]
(1) HC> HD>HB> HA (2) HC> HD> HA>HB (3) HD> HC>HB> HA (4) HC> HA> HD>HB
8. The most stable carbocation for the following is: [30 Jan, Shift - 2 - 2023]
NH2 NH2 NH2 NH2
(a) (b) (c) (d)

(1) c (2) d (3) b (4) a
9. The correct order of pKa values for the following compounds is: [30 Jan, Shift - 2 - 2023]
OH OH OH
OH
N NO2
(a) (b) (c) (d)
(1) c > a > d > b (2) b > d > a > c (3) b > a > d > c (4) a > b > c > d

10. Number of compounds from the following which will not dissolve in cold NaHCO 3 and
NaOH solutions but will dissolve in hot NaOH solution is_____ . [30 Jan, Shift - 2 - 2023]
O O
OH O
,
O O
H
O
,
O
OH O
O
H O H3C CH3 ,
ISOMERISM
11. Which of the following conformations will be the most stable? [25 Jan, Shift – 1 - 2023]
Me
Me
H H Me
(1) (2)
H H
H H
Me H H
Me
Me
H H
Me
(3) (4)
H H H Me
H H
H
12. The isomeric deuterated bromide with molecular formula C 4H8DBr having two chiral
carbon atoms is [25 Jan, Shift – 2 - 2023]
(1) 2–Bromo–1–deuterobutane (2) 2–Bromo–2–deuterobutane
(3) 2–Bromo–3–deuterobutane (4) 2–Bromo–1–deutero–2–methylpropane

13. Testosterone, which is a steroidal hormone, has the following structure.
[1 Feb, Shift – 2 - 2023]
OH
CH3
CH3
O
Testosterone
The total number of asymmetric carbon atom/s in testosterone is ______
14. The total number of chiral compound/s from the following is ________.
[1 Feb, Shift – 1 - 2023]
Ph
OH
O O CI
COOH
OH
COOH HO OH
OH
HO OH
COOH
OH
CH2
HO2C COOH

HYDROCARBON
15. In the following given reaction 'A' is [24 Jan, Shift – 1 - 2023]
CH3
C CH2
+ HBr ‘A’
Major Product
CH3 CH3 CH3 CH3

CH3 Br
Br
Br
CH3 Br
(1) (2) (3) (4)
16. Find out the major products from the following reactions. [24 Jan, Shift – 2 - 2023]
Hg(OAc)2,H2O BH3, THF

B
NaBH4 H2O2/OH– A
OH
OH , B=
(1) A = OH
, B= (2) A = OH
OH OH
(3) A = , B= (4) A = OH , B= OH
17. Maximum number of isomeric monochloroderivatives which can be obtained from

2,2,5,5-tetramethylhexane by chlorination is _________ [24 Jan, Shift – 2 - 2023]
? PhCOOH + PhCH2OH
18.
P Q R
The correct sequence of reagents for the preparation of Q and R is:

[25 Jan, Shift – 1 - 2023]
(1) (i) Cr2O3, 770 K, 20 atm ;(ii) CrO2Cl2, H3O+ ;(iii) NaOH ;(iv) H3O+
(2) (i) CrO2Cl2, H3O+ ; (ii) Cr2O3, 770 K, 20 atm;(iii) NaOH ; (iv) H3O+
(3) (i) KMnO4, OH– ; (ii) Mo2O3, A; (iii) NaOH ;(iv) H3O+
(4) (i) Mo2O3,  ; (ii) CrO2Cl2, H3O+ ; (iii) NaOH ;(iv) H3O+

19. The major products ‘A’ and ‘B’, respectively, are [30 Jan, Shift - 1 - 2023]
CH3
Cold H2SO4
‘A’ H3C – C = CH2 ‘B’
H2SO4 80°C
CH3 CH3 CH3
(1) H3C – C = CH3 & CH3 – C = CH C CH3
OSO3H CH3
CH3 CH3 CH3
(2) CH3 – C = CH C CH3 & CH3 – C = CH3
CH3 OSO3H
CH3 CH3 CH3
(3)CH3 – CH – CH2 – CH2 – CH – CH2 & H3C – C – CH3
OSO3H
CH3 CH3 CH3
(4) H3C – C – CH3 & CH3 – CH – CH2 –CH2 – HC – CH3
OSO3H
20. Choose the correct set of reagents for the following conversion
trans (Ph – CH=CH–CH3)cis (Ph – CH=CH–CH3) [31 Jan, Shift - 1 - 2023]
(1) Br2, alcKOH, NaNH2, Na(LiqNH3)
(2) Br2, alcKOH, NaNH2, H2/Lindlar Catalyst
(3) Br2, aqKOH, NaNH2, H2/Lindlar Catalyst
(4) Br2, aqKOH, NaNH2, Na(LiqNH3)
21. A hydrocarbon ‘X’ with formula C6H8 uses two moles of H2 on catalytic hydrogenation of
its one mole. On ozonolysis, ‘X’ yields two moles of methane dicarbaldehyde. The
hydrocarbon ‘X’ is: [31 Jan, Shift - 2 - 2023]
(1) hexa-1,3,5-triene (2) 1-methylcyclopenta-1,4–diene
(3) cyclohexa-1,3-diene (4) cyclohexa-1,4–diene
22. But-2-yne is reacted separately with one mole of Hydrogen as shown below:
Na H /Pd/C
B 
liq NH
 CH3  C  C  CH3 
2

A
3
Identify the incorrect statements from the optionsgiven below:

A. A is more soluble than B.
B. The boiling point & melting point of A are higher and lower than B respectively.
C. A is more polar than B because dipole moment of A is zero.
D. Br2 adds easily to B than A. [1 Feb, Shift – 1 - 2023]
(1) B and C only (2) B, C and D only
(3) A, C and D only (4) A and B only
HALOGEN DERIVATIVES
23. Assertion A : Hydrolysis of an alkyl chloride is aslow reaction but in the presence of NaI,
the rate ofthe hydrolysis increases.
Reason R : I– is a good nucleophile as well as a good leaving group.
below. [24 Jan, Shift – 1 - 2023]
(1) A is false but R is true
(2) A is true but R is false
(3) Both A and R are true and R is the correct explanation of A
(4) Both A and R are true but R is NOT the correct explanation of A
24. Number of moles of AgCl formed in the following reaction is _______.
[24 Jan, Shift – 1 - 2023]
CI
CI
CI
AgNO3
(A) + xAgCI 
H
CI
25. Identify the correct order for the given property for following compounds
(A) Boiling Point: CI < CI < CI
(B) Density: Br < CI < I
Br Br
Br
(C) Boiling Point: Br < Br < Br
Br < CI
(D) Density: I<
Br Br

CI > CI
(E) Boiling Point: CI >
Choose the correct answer from the option given below :- [29 Jan, Shift - 1 - 2023]
(1) (B), (C) and (D) only (2) (A), (C) and (E) only
(3) (A), (C) and (D) only (4) (A), (B) and (E) only
26. The one giving maximum number of isomeric alkenes on dehydrohalogenation reaction is
(excluding rearrangement) [29 Jan, Shift - 2 - 2023]
(1) 1-Bromo-2-methylbutane (2) 2-Bromopropane
(3) 2-Bromopentane (4) 2-Bromo-3,3-dimethylpentane
List I List II
CI CH3 I FittingReaction
A
+ CH3CI Na
CI II Wurtz Fittingreaction
B
+2Na 
+ –
N2 CI CI III FinkelsteinReaction
C
Cu2CI2
+N2
D C 2H5 CI  NaI  C 2H5I  NaCI IV Sandmeyerreaction
[30 Jan, Shift - 1 - 2023]

(1) A – II, B – I, C – III, D – IV (2) A – III, B – II, C – IV, D – I
(3) A – IV, B – II, C – III, D – I (4) A – II, B – I, C – IV, D – III
28. Decreasing order towards SN1 reaction for the following compounds is:
CI CI CI CI
NO2 OMe CI
(a) (b) (c) (d)
(1) a> c > d > b (2) a > b > c > d

(3) b> d > c > a (4) d > b > c > a

29. The correct order of melting point of dichlorobenzenes is [31 Jan, Shift - 1 - 2023]
CI CI CI CI CI CI
CI CI
(1) > > (2) > >
CI CI
CI
CI CI CI CI CI CI
CI CI
(3) > > (4) > >
CI CI
CI CI
30. In the following halogenated organic compounds the one with maximum number of
chlorine atoms in its structure is: [31 Jan, Shift - 2 - 2023]
(1) Chloral (2) Gammaxene (3) Chloropicrin (4) Freon -12
31. Identify the incorrect option from the following: [1 Feb, Shift – 1 - 2023]
Br OH
(1) KOH (aq)  + KBr
Br
KOH (alc) 
(2)
OH + KBr
CI CI O
O
anhyd AICI3 CH3 + HCI
(3) + H3C – C – CI
CI OH
(i) NaOH, 623 K, 300 atm
(4)
(ii) HCI

32. The graph which represents the following reaction is : [1 Feb, Shift – 2 - 2023]
 C6H5 3 C  CI    C6H5 3 C  OH


OH
Pyridine
rate rate
(1) (2)
[(C6H5)3C–CI] [OH–]
rate rate
(3) (4)
[(C6H5)3C–CI] [Pyridine]
ALCOHOL ETHER
33. 'A' and 'B' formed in the following set of reactions are : [24 Jan, Shift – 1 - 2023]
Br Br OH Br
(1)A = , B = (2)A = , B =
CH2O Br CH2Br OCH3
OH OH OH OH
(3)A = , B = (4)A = ,B =
CH2Br Br CH2Br OH
34. Find out the major product from the following reaction. [25 Jan, Shift – 2 - 2023]
H2SO4 (Concentrated)

OH

(1) (2) (3) (4)
35. Find out the major product for the following reaction. [29 Jan, Shift - 2 - 2023]
CH3
H3O+
Major Product

OH
(1) (2) (3) (4)
36. Decreasing order of dehydration of the following alcohols is [1 Feb, Shift – 1 - 2023]
OH OH OH OH
a b c d
(1) a> d > b > c (2) b > d > c > a (3) b > a > d > c (4) d > b > c > a
CARBONYL COMPOUND
37. Compound (X) undergoes following sequence ofreactions to give the Lactone (Y).
OH O
(i) HCHO, KOH H
Compound (X) (ii) KCN(alc) O Lactone (Y)
(iii) H3O+ H3C
CH3
[24 Jan, Shift – 1 - 2023]
CH3 CH3
(1) H C CHO (2) HOH2C C CHO
CH3 CH3
H2C CH2 CHO

(3) H2C CH2 CH2 CH2 CHO (4)
OH CH3

38. 'R' formed in the following sequence of reaction is: [24 Jan, Shift – 1 - 2023]
O
NaCN EtOH (i) 2MeMgBr ‘R’

‘P’ + ‘Q’ +
HOAc H (ii) H3O Major product
CI
OH OH
Me Me
Me Me
(1) (2)
Me Me OH Me
CN CI
OH OH
Me
Me Me Me
(3) (4)
CI CN
39. Given below are two statements : one is labelled as Assertion A and the other is labelled
as Reason R :
Assertion A :Acetal/Ketal is stable in basic medium.
Reason R : The high leaving tendency of alkoxideion gives the stability to acetal/ketal in
basic medium.
below : [25 Jan, Shift – 1 - 2023]
(4) Both A and R are true but R is NOT the correct explanation of A
40. Number of compounds giving (i) red colouration with ceric ammonium nitrate and also (ii)
positiveiodoform test from the following is _______ [25 Jan, Shift – 2 - 2023]

41. Match List I with List II. [29 Jan, Shift - 1 - 2023]
List-I List-II
Reaction Reagents
(A) Hoffmann (I) Conc. KOH, 
(B) Clemmensen reduction (II) CHCI3, NaOH/H3O+
(C) Cannizaro reaction (III) Br2, NaOH
(D) Reimer-Tiemann reaction (IV) Zn-Hg/HCI
(1) (A) – III, (B) – IV, (C) – II, (D) – I (2) (A) – II, (B) – IV, (C) – I, (D) - III
(3) (A) – III, (B) – IV, (C) – I, (D) – II (4) (A) – II, (B) – I, (C) – III, (D) - IV
42. 17 mg of a hydrocarbon (M.F. C10H16) takes up8.40 mL of the H2 gas measured at 0ºC
and 760mm of Hg. Ozonolysis of the same hydrocarbon yields [29 Jan, Shift - 1 - 2023]
CH3 – C – CH3, H–C–H, H–C–CH2 – CH2 – C – C – H
O O O O O
The number of double bond/s present in thehydrocarbon is ________ .
43. Find out the major products from the following reaction sequence.
[29 Jan, Shift - 2 - 2023]

CO2H OH
OH OH
(1) A = B = CI Me
Me Me
CI
HO
CO2Et
OH OH
(2) A = B = CI Me
Me Me
CI
CN OH
OH NH2
(3) A = B = CI Me
Me Me
CI
NC OH
(4) A = OH OH
B= H
CI Me Me

44. Consider the following reaction
i dil.NaOH
Propanal+ Methanal = 
ii  Pr oduct B
iii NaCN  C5H8O3 
iv  H3 O

The correct statement for product B is. It is [31 Jan, Shift - 1 - 2023]
(1) optically active and adds one mole of bromine
(2) racemic mixture and is neutral
(3) racemic mixture and gives a gas with saturated NaHCO 3 solution
(4) optically active alcohol and is neutral
45. 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:
[31 Jan, Shift - 2 - 2023]
O O O O O
OH
(1) (2) (3) (4)
46. The number of molecules which gives haloform test among the following molecules is
______. [31 Jan, Shift - 2 - 2023]
O
O
O O
OEt
O O
OH
OH
47. Number of isomeric compounds with molecularformula C9H10O which (i) do not dissolve in
NaOH (ii) do not dissolve in HCl. (iii) do not give orangeprecipitate with 2, 4 – DNP (iv) on
hydrogenationgive identical compound with molecular formulaC 9H12O is __________ .
[1 Feb, Shift – 1 - 2023]

48. The structures of major products A, B and C in the following reaction are sequence.
O
NaHSO3, dil. HCI LiAIH4
H [A] [B]
NaCN, H2O
HCI/H2O [1 Feb, Shift – 2 - 2023]
[C]

OH OSO3 Na
CN
A= , A=
H H ,
HO OH
CHO
B= B=
H , H ,
(1) (2) CI
HO CO2H
C= C=
H H
HO SO3H HO CN
A= , A= ,
H H
HO NH2
B= B=
OH , H ,
(3) (4)
HO SO3CI HO CO2H
C= C=
H H
OXIDATION REDUCTION
49. Given below are two Statements :

O
H2N
Statement I: under Clemmensen reduction conditions will give
O
HOOC
Statement II: under Wolff-Kishner reduction condition will give

CI
CI

below : [24 Jan, Shift – 2 - 2023]
(1) Statement I is false but Statement II is true
(2) Both Statement I and Statement II are false
(3) Statement I is true but Statement II is false
(4) Both Statement I and Statement II are true
50. Given below are two statements, one is labelled as Assertion A and the other is labelled
as Reason R Assertion A : Beryllium has less negative value of reduction potential
compared to the other alkaline earth metals.
Reason R : Beryllium has large hydration energy due to small size of Be2+ but relatively
large value of atomization enthalpy. In the light of the above statements, choose the most
appropriate answer from the options given below. [24 Jan, Shift – 2 - 2023]
(1) A is correct but R is not correct
(3) A is not correct but R is correct
(4) Both A and R are correct and R is NOT the correct explanation of A.
51. The major product „P  for the following sequenceof reactions is:
[29 Jan, Shift - 1 - 2023]
O O (1) Zn/Hg
‘P’
Ph HCI
NH2 major product
(2) LiAIH4
(3) H3O+
OH OH
(1) Ph OH (2) Ph NH2
OH OH
(3) Ph NH2 (4) Ph NH2
52. A trisubstituted compound ‘A’, C10H12O2 gives neutral FeCl3 test positive. Treatment of
compound ‘A’ with NaOH and CH3Br gives C11H14O2 , with hydroiodic acid gives
methyliodide and with hotconc. NaOH gives a compound B, C10H12O2 . Compound ‘A’
also decolorizes alkaline KMnO4. The number of  bond/spresent in the compound ‘A’ is
_______. [30 Jan, Shift - 1 - 2023]

53. Given below are two statements: One is labelled as Assertion A and the other is labelled
as Reason R.
O
Assertion A : can be easily reduced using Zn-Hg/HCl to

OH OH
Reason R : Zn-Hg/HCl is used to reduce carbonyl group to –CH2 – group.

below:
(3) Both A and R are true but R is not the correct explanation of A
CARBOXYLIC ACID
54. ‘A’ in the given reaction is
H
OH COOH
H+
+ ‘A’
O Major
[25 Jan, Shift – 2 - 2023]
O OH O
O
(1) (2)
O O
O OH
COOH
(3) OH C O (4)
O
55. In the following reaction, ‘A’ is
‘A’ Major product. [1 Feb, Shift – 1 - 2023]

(1) (2)
(3) (4)
AMINES
56. Given below are two statements:

Statement I: Pure Aniline and other arylamines are usually colourless.
Statement II: Arylamines get coloured on storage due to atmospheric reduction.
In the light of the above statements, choose the most appropriate answer from the options
given below: [24 Jan, Shift – 2 - 2023]
(1) Both Statement I and Statement II are incorrect
(2) Both Statement I and Statement II are correct
(3) Statement I is correct but Statement II is incorrect
(4) Statement I is incorrect but Statement II is correct
57. Choose the correct colour of the product for the following reaction.
[24 Jan, Shift – 2 - 2023]
N = N – OOCCH3
+1– Naphthyl amine 
SO3H
(1) Yellow (2) White (3) Red (4) Blue
58. Reaction of propanamide with Br2/ KOH (aq) produces: [29 Jan, Shift - 2 - 2023]
(1) Ethylnitrile (2) Propylamine (3) Propanenitrile (4) Ethylamine
59. Benzylisocyanidecan be obtained by: [30 Jan, Shift - 1 - 2023]
CO2Br CH2NH2
(A) (B) CHCI3
AgCN
Ag. KOH
CH2 – NHCH3 CH2OTs

(C) CHCI3 (D) KCN
Ag. KOH

Choose the correct answer from the options given
below :
(1) A and D (2) Only B (3) A and B (4) B and C
60. An organic compound [A] (C4H11N), show soptical 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: [31 Jan, Shift - 2 - 2023]
Me
(1) NH2 (2) N
Me
Me
NH2
(3) (4)
N
Me
AROMATIC COMPOUND
61. The compound which will have the lowest ratetowardsnucleophilic aromatic
substitutionontreatment with OH– is [25 Jan, Shift – 1 - 2023]
CI
CI CI CI
NO2 NO2
(1) (2) (3) (4)

NO2
NO2 NO2
62. Identify the product formed (A and E) [25 Jan, Shift – 1 - 2023]
Me
Br2 Sn/HCI NaNO2/HCI H PO /H O (i) KMnO4/KOH

A B C 3 2 2 D E
273 – 278 K (ii) H3O+
NO2

CI
COOH
Br
Br
(1) A = , E=
Br
Br
NO2
Me
COOH
Br
(2) A = , E=
Br
NO2
Me
Me
Br
(3) A = , E=
Br
NO2
Me
COOH
Br
Br
(4) A = , E=
NO2
OH
63. In the cymene to phenol preparation in presence of air, the intermediate is

[25 Jan, Shift – 1 - 2023]
O
O O
CH3 O–O–H
(1) (2) (3) (4)

CH3 CH3
64.
Br Br
NO2
(Y)
(X)
In the above conversion of compound (X) toproduct (Y), the sequence of reagents to be
used will be: [30 Jan, Shift - 2 - 2023]
+
(1) (i) Br2, Fe (ii) Fe, H (iii) LiAlH4 (2) (i) Br2(aq) (ii) LiAlH4 (iii) H3O+
(3) (i) Fe, H+ (ii) Br2(aq) (iii) HNO2 (iv) CuBr (4) (i) Fe, H+ (ii) Br2(aq) (iii) HNO2 (iv) H3PO2
NO2
65. H2/Pd (CH3CO)2O [31 Jan, Shift - 1 - 2023]
[A] [B]
C2H5OH Pyridine
O
O
C NH2
CH2 C CH2NH2
(1) (2)
O O
C C
NHCH2 OH NH CH3
(3) (4)
66. An organic compound ‘A’ with empirical formula C6H6O gives sooty flame on burning. Its
reaction with bromine solution in low polarity solventresults in high yield of B. B is
[31 Jan, Shift - 1 - 2023]
OH Br
CH2CH2Br Br CH2CH3
OH
(1) (2) (3) (4)
Br
O O
Br

67. How many of the transformation given below would result in aromatic amines?
CI
O O
NH2 + Br2 + NaOH

(1) (2) NK
NHCOCH3
NO2
H2 dil H2SO4
(3) (4) 
Pd/C
68. In a reaction,
OH OH OCOCH3
COOCH3 COOH COOH
‘Y’ ‘X’
reagents ‘X’ and ‘Y’ respectively are : [1 Feb, Shift – 2 - 2023]

(1) (CH3CO)2O/H+ and CH3OH/H+,  (2) (CH3CO)2O/H+ and (CH3CO)2O/H+
(3) CH3OH/H+,  and CH3OH/H+,   (4) CH3OH/H+ and (CH3CO)2O/H+
+ HF
X
69. ‘X’ is: 
Major product
[1 Feb, Shift – 2 - 2023]
(1) (2) (3) (4)

BIOMOLECULES
70. Total number of tripeptides possible by mixing of valine and proline is _________
[24 Jan, Shift – 2 - 2023]
71. Match items of Row I with those of Row II. [25 Jan, Shift – 1 - 2023]
Row-I Row-II
CH2OH
O H
H
H
(P) OH H (i) -D-(–) Fructofuranose.
OH OH
H OH
CH2OH
O
H OH
H
(Q) OH H (ii) -D-(–) Fructofuranose
OH H
H OH
HOCH2 O CH2OH
(R) HH OH OH (iii) -D-(–) Glucopyranose.
OH H
HOCH2 O OH
(S) HH HO CH OH
2
(iv) -D-(–) Glucopyranose
OH H
Correct match is
(1) Piv, Qiii, Ri, Sii (2) Pi, Qii, Riii, Siv
(3) Piii, Qiv, Rii, SI (4) Piii, Qiv, Ri, Sii
72. Number of cyclic tripeptides formed with 2 aminoacids A and B is:
[29 Jan, Shift - 1 - 2023]
(1) 2 (2) 3 (3) 5 (4) 4

73. Following tetrapeptide can be represented as
COOH
CH2Ph O
O CH2
H H
N N C – OH
H2N N
H
CH2 CH2
CN
H3C CH3
OH
(F, L, D, Y, I, Q, P are one letter codes for amino acids) [29 Jan, Shift - 2 - 2023]
(1) FIQY (2) FLDY (3) YQLF (4) PLDY
74. Given below are two statements : one is labelled as [30 Jan, Shift - 1 - 2023]
Assertion (A) and the other is labelled as Reason(R).
Assertion (A) : Ketoses give Seliwanoff’s testfaster than Aldoses.
Reason (R) : Ketoses undergo -elimination followed by formation of furfural.
below :
(1) (A) is false but (R) is true
(2) Both (A) and (R) are true and (R) is the correct explanation of (A)
(3) (A) is true but (R) is false
(4) Both (A) and (R) are true but (R) is not the correct explanation of (A)
75. 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
peptidelinkages in it are _______ .
76. A protein ‘X’ with molecular weight of 70,000 u,on hydrolysis gives amino acids. One of
the seamino acid is [31 Jan, Shift - 1 - 2023]
CH3
(1) NH2 – CH2 – CH – CH2 CH2 COOH (2) CH3 – CH – CH2 – CH – COOH
CH3 NH2
CH3 CH3
(3) CH3 – CH – CH2 – CH – COOH (4) CH3 – C – CH2 – CH2 COOH
NH2 NH2

77. The correct representation in six memberedpyranoseform for the following sugar [X] is
CHO
HO H
HO H
H OH
H OH
CH2OH
Sugar[x]
[1 Feb, Shift – 1 - 2023]

CH2OH CH2OH
O O
H H
H H
(1) (2)
OH H OH OH OH
OH HO OH
H OH H OH
CH2OH CH2OH
O O
HO H H H H H
(3) OH OH (4) OH OH
H H HO H
OH OH OH OH
78. Match List I and List II

List I List II
Test Functional group /
Class of Compound
(A) Molisch's Test (I) Peptide
(B) Biuret Test (II) Carbohydrate
(C) Carbylamine Test (III) Primary amine
(D) Schiff s Test (IV) Aldehyde
Choose the correct answer from the options givenbelow: [1 Feb, Shift – 1 - 2023]
(1) (A) – I, (B) – II, (C) – III, (D) – IV (2) (A) – III, (B) – IV, (C) –I, (D) – II
(3) (A) – II, (B) – I, (C) – III, (D) – IV (4) (A) – III, (B) – IV, (C) –II, (D) – I

79. All structures given below are of vitamin C. Most stable of them is :
[1 Feb, Shift – 2 - 2023]
OH OH
HO O HO O
O O
H H
(1) (2)
OH OH O OH
OH OH
O HO O
HO O
H H
(3) (4)
OH O
O OH
80. Given below are two statements : one is labeled as Assertion (A) and the other is labelled
as Reason (R).
Assertion (A) :-halocarboxylic acid on reaction with dil. NH3 gives good yield of -amino
carboxylic acid whereas the yield of amines is very low when prepared from alkyl halides.
Reason (R) : Amino acids exist in zwitter ion form in aqueous medium.
below : [1 Feb, Shift – 2 - 2023]
(1) Both (A) and (R) are correct and (R) is the correct explanation of (A).
(2) Both (A) and (R) are correct but (R) is not the correct explanation of (A).
(3) (A) is correct but (R) is not correct.
(4) (A) is not correct but (R) is correct.
POLYMER
List I (Name of polymer) List II (Uses)

A. Glyptal I. Flexible pipes
B. Neoprene II. Synthetic wool
C. Acrilan III. Paints and Lacquers
D. LDP IV. Gaskets
Choose the correct answer from the options given below:-

[25 Jan, Shift – 2 - 2023]
(1) A-III, B-II, C-IV, D-I (2) A-III, B-IV, C-II, D-I
(3) A-III, B-IV, C-I, D-II (4) A-III, B-I, C-IV, D-II

82. Match List-I and List-II.
List-I List-II
A. ElastomericPolymer I. Urea formaldehydeResin
B. Fibre polymer II. Polystyrene
C. Thermosetting Polymer III. Polyester
D. ThermoplasticPolymer IV. Neoprene
Choose the correct answer from the options given below: [29 Jan, Shift - 2 - 2023]
(1) A-II, B-III, C-I, D-IV (2) A-II, B-I, C-IV, D-III
(3) A-IV, B-III, C-I, D-II (4) A-IV, B-I, C-III, D-II
83. Caprolactam when heated at high temperature in presence of water, gives
[30 Jan, Shift - 1 - 2023]
(1) Teflon (2) Dacron (3) Nylon 6, 6 (4) Nylon 6
CHEMISTRY IN EVERYDAY LIFE
84. Given below are two statements:

Statement I : Noradrenaline is a neurotransmitter.
Statement II : Low level of noradrenaline is notthe cause of depression in human.
In the light of the above statements, choose thecorrect answer from the options given
below [24 Jan, Shift – 1 - 2023]
(1) Statement I is correct but Statement II is incorrect
(2) Statement I is incorrect but Statement II is correct
(3) Both Statement I and Statement II are correct
(4) Both Statement I and Statement II are incorrect
LIST I TYPE LIST II NAME
A. Antifertility drug I. Norethindrone
B. Tranquilizer II. Meprobomate
C. Antihistamine III. Seldane
D. Antibiotic IV. Ampicillin
Choose the correct answer from the options given below: [24 Jan, Shift – 2 - 2023]
(1) A-II, B-I, C-III, D-IV (2) A-IV, B-III, C-II, D-I
(3) A-I, B-III, C-II, D-IV (4) A-I, B-II, C-III, D-IV

86. Which of the following statements is incorrect for antibiotics? [25 Jan, Shift – 1 - 2023]
(1) An antibiotic must be a product of metabolism.
(2) An antibiotic is a synthetic substance produced as a structural analogue of naturally
occurring antibiotic.
(3) An antibiotic should promote the growth orsurvival of microorganisms.
(4) An antibiotic should be effective in low concentrations.
87. Given below are two statements, one is labelled as
Assertion A and the other is labelled as Reason R
Assertion A:-Butylated hydroxyl anisole when added to butter increases its shelf life.
Reason R:-Butylated hydroxyl anisole is more reactive towards oxygen than food.
given below:- [25 Jan, Shift – 2 - 2023]
(2) A is correct but R is not correct.
(3) A is not correct but R is correct.
(4) Both A and R are correct but R is NOT the correct explanation of A.
88. Match List I with List II [29 Jan, Shift - 1 - 2023]
List I List II
Antimicrobials Names
(A) Narrow spectrum Antibiotic (I) Furacin
(B) Antibiotic (II) Sulphur dioxide
(C) Disinfectants (III) Penicillin-G
(D) Broad spectrum antibiotic (IV) Chloramphenicol
(1) (A) – III, (B) – I, (C) – II, (D) – IV
(2) (A) – I, (B) – II, (C) – IV, (D) - III
(3) (A) – II, (B) – I, (C) – IV, (D) – III
(4) (A) – III, (B) – I, (C) – IV, (D) - II
89. A doctor prescribed the drug Equanil to a patient.The patient was likely to have
symptoms of which disease? [29 Jan, Shift - 2 - 2023]
(1) Stomach ulcers
(2) Hyperacidity
(3) Anxiety and stress
(4) Depression and hypertension
90. Amongst the following compounds, which one is an antacid? [30 Jan, Shift - 1 - 2023]
(1) Ranitidine (2) Meprobamate
(3) Terfenadine (4) Brompheniramine

91. Given below are two statements: One is labelled as
Assertion A and the other labelled as Reason R.
Assertion A: Antihistamines do not affect thesecretion of acid in stomach.
Reason R :Antiallergic and antacid drugs work ondifferent receptors.
below:
(2) Both A and R are true and R is the correctexplanation of A
(4) Both A and R are true but R is not the correctexplanation of A.
92. Which of the following artificial sweeteners has the highest sweetness value in
comparison to canesugar? [31 Jan, Shift - 1 - 2023]
(1) Aspartame (2) Sucralose (3) Alitame (4) Saccharin
93. Which of the following compounds are not used asdisinfectants?
(A) Chloroxylenol (B) Bithional (C) Veronal (D) Prontosil (E) Terpineol
Choose the correct answer from the options given below: [31 Jan, Shift - 2 - 2023]
(1) A, B, E (2) A, B (3) B, D, E (4) C, D
List-I List-II
(A) Tranquilizers (I) Anti blood clotting
(B) Aspirin (II) Salvarsan
(C) Antibiotic (III) Antidepressant drugs
(D) Antiseptic (IV) Soframicine
Choose the correct answer from the options given below: [1 Feb, Shift – 1 - 2023]
(1) (A) – IV, (B) – II, (C) – I, (D) – III (2) (A) – II, (B) – I, (C) – III, (D) – IV
(3) (A) – III, (B) – I, (C) – II, (D) – IV (4) (A) – II, (B) – IV, (C) – I, (D) – III
95. Among the following, the number of tranquilizer/s is/are_________.

[1 Feb, Shift – 2 - 2023]
A. Chloroliazepoxide B. Veronal C. Valium D. Salvarsan

PRACTICAL ORGANIC CHEMISTRY
96. Compound that will give positive Lassaignestestfor both nitrogen and halogen is
[29 Jan, Shift - 1 - 2023]
(1) N2H4.HCl (2) CH3NH2.HCl
(3) NH4Cl (4) NH2OH.HCl
97. Following chromatogram was developed by adsorption of compound „A on a 6 cm TLC
glassplate. Retardation factor of the compound „ A is______ × 10–1.
[29 Jan, Shift - 1 - 2023]
0.5 cm
Solvent Front
Compound A
3.5 cm
0.5 cm
98. Which of the following compounds would give the following set of qualitative analysis?
(i) Fehling’s Test: Positive
(ii) Na fusion extract upon treatment with sodium nitroprusside gives a blood red colour
but not [30 Jan, Shift - 1 - 2023]
N N
(1) CHO (2) CHO

N O
N N
(3) CHO (4)

CHO
S S
99. Match List I with List II:

List I (Mixture) List II (Separation Technique)
(A) CHCI3 + C6H5NH2 I Steam distillation
(B) C6H14+ C5H12 II Differential extraction
(C) C6H5NH2+ H2O III Distillation
(D) Organic compound in H2O IV Fractional distillation

(1) A-IV, B-I, C-III, D-II (2) A-III, B-IV, C-I, D-II
(3) A-II, B-I, C-III, D-IV (4) A-III, B-I, C-IV, D-II
100. Match items of column I and II
Column I (Mixture of compounds) Column II (Separation Technique)

A. H2O/CH2Cl2 i. Crystallization
O OH
ii. Differential solvent extraction
B.
NO2
C. Kerosene/Naphthalene iii. Column chromatography
D. C6H12O6 /NaCl iv. Fractional Distillation
Correct match is: [31 Jan, Shift - 1 - 2023]

(1) A-(iii), B-(iv), C-(ii), D-(i) (2) A-(i), B-(iii), C-(ii), D-(iv)
(3) A-(ii), B-(iii), C-(iv), D-(i) (4) A-(ii), B-(iv), C-(i), D-(iii)
101. In Dumas method for the estimation of N2, the sample is heated with copper oxide and
the gas evolved is passed over : [31 Jan, Shift - 2 - 2023]
(1) Ni (2) Copper gauze (3) Pd (4) Copper oxide
102. Given below are two statements :
Statement I :Sulphanilic acid gives esterification test for carboxyl group.
Statement II :Sulphanilic acid gives red colour in Lassigne’s test for extra element
detection.
given below : [1 Feb, Shift – 2 - 2023]
(1) Statement I is correct but Statement II is incorrect.
(2) Both Statement I and Statement II are incorrect.
(3) Both Statement I and Statement II are correct.
(4) Statement I is incorrect but Statement II is correct.

ANSWER-KEY
1. (BONUS) 2.(3) 3.(1) 4.(1) 5.(4) 6. (2) 7.(2) 8.(1) 9.(2) 10. (3)
11.(1) 12.(3) 13. (6) 14. (2) 15. (4) 16.(1) 17.(3) 18.(1) 19.(1) 20.(2)
21.(4) 22.(Bonus) 23.(3) 24.(2) 25.(2) 26.(3) 27.(4) 28.(3) 29.(4)
30.(2) 31.(2) 32.(3) 33.(4) 34.(1) 35.(2) 36.(2) 37.(1) 38.(2) 39.(1)
40.(3.00) 41.(3) 42.(3) 43.(2) 44.(3) 45.(1) 46.(3) 47.(2) 48.(4) 49.(3)
50.(2) 51. (3) 52. (4) 53. (1) 54.(2) 55.(2) 56.(3) 57. (3) 58. (4) 59.(3)
60.(4) 61.(4) 62. (2) 63.(4) 64.(4) 65.(4) 66.(1) 67.(3) 68. (1) 69. (1)
70.(8) 71.(4) 72.(4) 73.(2) 74.(3) 75. (6) 76.(2) 77.(2) 78. (3) 79. (1)
80. (2) 81.(2) 82.(3) 83.(4) 84. (1) 85.(4) 86.(3) 87.(1) 88.(1) 89. (4)
90.(1) 91. (2) 92.(3) 93.(4) 94. (3) 95. (3) 96.(2) 97. (6) 98. (4) 99. (2)
100.(3) 101. (2) 102. (4)

Chaptewise PYQ 2023 Organic Chemistry

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C H E M IS TR Y

ORGANIC CHEMISTRY CHAPTERWISE QUESTION BANK

1. Increasing order of stability of the resonance structure is :

MeO OMe OMe

(1) a only (2) c only (3) Both a and c (4) b only

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List I (Amines) List II

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

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The total number of asymmetric carbon atom/s in testosterone is ______

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CH3 CH3 CH3 CH3

Hg(OAc)2,H2O BH3, THF

17. Maximum number of isomeric monochloroderivatives which can be obtained from

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

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CH3 CH3 CH3

(1) H3C – C = CH3 & CH3 – C = CH C CH3

CH3 CH3 CH3

(2) CH3 – C = CH C CH3 & CH3 – C = CH3

(3)CH3 – CH – CH2 – CH2 – CH – CH2 & H3C – C – CH3

(4) H3C – C – CH3 & CH3 – CH – CH2 –CH2 – HC – CH3

Identify the incorrect statements from the optionsgiven below:

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(B) Density: Br < CI < I

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D C 2H5 CI  NaI  C 2H5I  NaCI IV Sandmeyerreaction

[30 Jan, Shift - 1 - 2023]

(1) a> c > d > b (2) a > b > c > d

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 C6H5 3 C  CI    C6H5 3 C  OH

CH2O Br CH2Br OCH3

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(1) (2) (3) (4)

(1) H C CHO (2) HOH2C C CHO

H2C CH2 CHO

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NaCN EtOH (i) 2MeMgBr ‘R’

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[29 Jan, Shift - 2 - 2023]

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(1) (2) (3) (4)

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49. Given below are two Statements :

Statement II: under Wolff-Kishner reduction condition will give

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Assertion A : can be easily reduced using Zn-Hg/HCl to

Reason R : Zn-Hg/HCl is used to reduce carbonyl group to –CH2 – group.

55. In the following reaction, ‘A’ is

‘A’ Major product. [1 Feb, Shift – 1 - 2023]

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56. Given below are two statements:

+1– Naphthyl amine 

CH2 – NHCH3 CH2OTs

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(1) NH2 (2) N

(1) (2) (3) (4)

Br2 Sn/HCI NaNO2/HCI H PO /H O (i) KMnO4/KOH

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63. In the cymene to phenol preparation in presence of air, the intermediate is