GOC& ISOMERISM Dexter Tutorials Sheet

Level-1

➢ I-EFFECT

1. Which of the following groups has the highest + I effect ?

(A) CH3 — (B) CH3 CH2 — (C) (CH3)2 CH — (D) (CH3)3 C —

2. Maximum –I effect is exerted by the group

(A) C6H5 — (B) — OCH3 (C) –Cl (D) –NO2

3. Zero inductive effect is exerted by -

(A) C6H5 — (B) H– (C) CH3— (D) Cl–

4. Pair of groups exerting (–I) effect is -

(A) – NO2 & – CH3 (B) – NO2 & – Cl

(C) – Cl & – CH3 (D) – CH3 & – C2H5

➢ M-EFFECT AND RESONANCE

5. 'M' effect is the resonance of -

(A) p electrons only (B) s electrons only

(C) p and s both (D) (+) ve and (–) charge.

6. M effect takes part in –

(A) Saturated system

(B) Unsaturated system containing conjugated double bond.

(C) Unsaturated system containing non conjugated double bond.

(D)A triple bond in a carbon chain

7. A group having '– A = B' type structure in which electro negativity of B is greater
than A which is attached to benzene ring the

E+ attack mostly at -

(A) 'm' position (B) 'O' – position (C) 'p' position (D) All

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
8. Which of the following pairs of structures do not represent resonating
structures ?

O OH
(A) CH3 – C – CH3 ; CH3 – C = CH2



(B) O ; O


OH OH

(C) CH3 – C – CH3 ; CH3 – C – CH3




(D) CH3 – C – OH ; CH3 – C = OH

O O
9. In which delocalization of positive charge is possible?
 
NH3 H H OH2 O
N 

(A) (B) (C) (D)

10. The o, p-directing but deactivating group is

(A) – NH2 (B) – OH (C) R-(alkyl) (D)X-(Halogen)

11. The order of stability of the following resonating structures


O O

CH2 = CH – C – H (I), CH2 – CH = C – H (II)

O

and CH2 – CH = C – H (III) is :

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

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
12. Which of the following is/are not correctly ordered for resonance stability -

  .. 
(A)CH2–CH= N=O CH2=CH– N =O CH2–CH=N–O
(I) (II) (III)
(II > I > III)

 ..  
N H2 = C = O 
⎯→ N H 2 – C = O 
⎯→ NH 2 – C  O
(B) ( I) (II) (III )
(I  III  II)

 
(C) H 3C – C = O 
⎯→ H 3C – C  O
( I) (II)
(I  II)

   O   O
(D) CH2–CH–N 
⎯→ CH2–CH=N
(I) O (II) O
(II>I)

➢ HYPERCONJUGATION
13. Hyperconjugation is possible in -

H H
C=C
H NH2
(i) C = CH – CD3 (ii)
H

H H CH3
C=C
(iii) H (iv)

CH2Me CH3

(A) i and ii (B) i, ii and iii (C) only ii (D) in all

14. The activating nature of – CH3 group linked to benzene ring can be explained

with the help of

(A) Hyperconjugation (B) Resonance effect

(C) Inductive effect (D) Electromeric effect

15. Which of the following groups has the highest hyperconjugative effect but

least + I-effect ?

(A) – CH3 (B) – CH2CH3 (C) – CH (CH3)2 (D) – C (CH3)3

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
16. Stability of following alkenes in the increasing order is –

(I) (II) (III) (IV)

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

17. Which of the following molecules has all the effects : inductive : mesomeric
and Baker Nathan effect ?

(A) C2H5Cl (B) CH3 – CH = CH2

(C) CH2 = CH – CH = CH2 (D) CH3 – CH = CH – C– CH3

18. The heat of hydrogenation of benzene is 51 kcal/mol and its resonance energy is
36 kcal/mol. What will be the heat of hydrogenation of cyclohexene ?

(A) 18 kcal mol–1 (B) 29 kcal mol–1

(C) 50 kcal mol–1 (D) 26 kcal mol–1

19. An organic molecules has 5 C=C bonds (heat of hydrogenation for C=C bond is
28.8 kJ mol–1) and experimental value for heat of hydrogenation is 99 kJ mol–1. The
resonance energy in kJ mol–1 is

(A) 45 (B) 90 (C) 70 (D) 140

➢ ELECTROMERIC EFFECT

20. Electromeric effect is -

(A) The effect in excited state

(B) p electrons remain in valency shell

(C) The shift of p electron as well as s electron

(D) Only p electrons are shifted

21. In > C = O the direction of pe–s shifting -

(A) are different for E+ and Nu– attack (B) are same for E+ and Nu– attack

(C) will depend upon attacking sight (D) None

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
➢ STABILITY OF INTERMEDIATES

22. The most stable free radical among the following is

• 2
(A) C6H5CH2CH • – CH3
(B)CH3 – CH • 3
(C) C6H5CHCH • 2
(D) CH3CH

23. Most stable carbocation is

 
(A) CH2 = CH (B) CH2 = CH – CH2


(C) CH2 (D)  CH3

24. The acceptable resonating structures of the following molecule are -

..
CH3 – CH = C – O
.. –CH2 – CH3
|
:N

H3C CH3

 
.. .. .. 
(x) CH3 – C H – C – O
.. – CH2 – CH3
(y) CH3 – C H – C = O
.. – CH2 – CH3
|| |
N :N

H3C CH3 H3C CH3

 ..  
(z) CH3 – C H – C – O
.. – CH2 – CH3
(w) CH3 – C H – C = O – CH2 – CH3
|| |
N :N

H3C CH3 H3C CH3

(A) x,y (B) x, z (C) y, z (D) z,w

25. Which of the following is most stable ?

 
(A) CH3 (B) CH3– CH2

 
(C) CH3– CH –CH3 (D) CH2=CH– CH2

26. Which of the following is most stable carbocations ?

O
CH3
 

(A) CH3 (B) CH3– CH2 (C) CH3 – C (D) CH3 – C – CH2

CH3

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
27. Which of the following is least stable carbocations?

   
(A) CH3 (B) CH3– CH2 (C) CH3–CH–CH3 (D) PhCH2

28. Which of the following is most stable ?

 
(A) CH3 (B) CH3–C – CH3

CH3

 
(C) F – C – F (D) Cl – C – Cl

F Cl
 
CH2 CH2

29. is more stable than because

NO2
NO2

(I) (II)


(A) 180º location of NO2 and CH2 in I

(B) – NO2 opperate both –I and – M in I.

(C) – I in II is weaker than I

(D) Due to steric repulsion

30. Which of the following is most stable ?

   
(A) CH3 (B) CH2= CH (C) CH  C (D) CH3–C  C


CH2

31. Hybridisation of carbanion in is -

(A) sp3 (B) sp2

(C) sp (D) Unhybridised

32. The hybridisation of carbanion is

(A) sp3 (B) sp2 (C) sp (D) All may be

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

33. Carbanion of CH3 – CH2 has geometry -

(A) Planer (B) Pyramidal

(C) Squar bipyramidal (D) Triangular bipyramidal

•
34. Hybridisation of R – CH2 is -

(A) sp3 (B) sp2 (C) sp (D) All of these

35. Arrange following compounds for their acidic strength order

CH 3 − C − CH 3 CH 3 − C − C − CH 3 CH 3 − C − CH 2 − C − CH 3
|| || || || ||
O O O O O
( I) (II) (III )

(A) I > II > III (B) III > II > I

(C) I > III > II (D) III > I > II

36. Which of the following can stabilize the carbon free radicals -

(A) + I effect (B) + M effect

(C) Hyperconjugation (D) All of these

37. Which of the following is not paramagnetic?

(A) Carbon free radical (B) Singlet carbene

(C) Triplet carbene (D) All

38. Which of the following are diamagnetic?

(A) Carbocation (B) Carbanion

(C) Singlet carbene (D) All

39. Arrange following carbocation according to decreasing order of stability -

CH3
CH3

  CH
(I) CH 3 − C H 2 (II) C H 3 (III) (IV)
CH3

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

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

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

40. Carbene is an -

(A) Electrophile (B) Nucleophile

(C) Very strong base (D) All of these

41. Unshared pair of electron is contained by -

(A) Carbanion (B) Singlet carbene

(C) Triplet carbene (D) Both A and B

42. Most stable carbanion is :


(A) HC  C (B) C6H5-

 
(C) (CH3)3C – CH2 (D) (CH3)2C = CH2

43. Consider the following carbocations

 
(A) CH3O CH2 (B) CH2

 
(C) CH3 CH2 (D) CH3 — CH 2

The relative stabilities of these carbocations are such that:-

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

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

➢ AROMATICITY
44. Which order is true for resonance energy?

(A) < (B) < 

O OH 
CH2

(C) < (D) >

NO2 N N
NO2 H H

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Br

AgNO3
45. Product (A)

Select the correct statement about product (A)

(A) Product is aromatic (B) Product has high dipole moment

(C) Product has less resonance energy (D) Both A and B

1 1 1
2 2 2
46. 3 3 3
4 4 4

There are three canonical structure of naphthalene. Examine & find correct
statement among the following

(A) All C–C bonds are of some length

(B) C-1 - C-2 bond is shorter than C2–C3 bond

(C) C1–C-2 bond is longer than C2–C3 bond

(D) None

47. In which of the following lone pair indicated is involved in resonance?

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

N N N N
H H

48. Which of the following is not an aromatic compound ?

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

S O


49. In which of the following molecules, the substituent does not exert its resonance
effect?


(A) C6H5NH2 (B) C 6 H 5 N H 3 (C) C6H5OH (D) C6H5Cl

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
50. Which of the following species would be expected to exhibit aromatic character
? Select the correct answer from the following :

I II III IV

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

51. Which of the following species is most stable ?

+ +
(A) p – O2N – C6H4 – C H 2 (B) C6H5 – C H 2

+ +
(C) p – Cl – C6H4 – C H 2 (D) p – CH3O – C6H4 – C H 2

➢ ACIDIC AND BASIC STRENGTH COMPARISION

52. Most acidic alcohol is –

(A) (CH3)3C–OH (B) CH3CH2OH (C) CH3OH (D) Propanol-2

53. Under suitable conditions C6H5CH2OH (A) C6H5OH (B), and C6H5COOH (C) can act
as acids. The increasing order of their acidic strength is -

(A) A < B < C (B) A < C < B

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

54. The greater volatility of 2-nitrophenol compared with the 4-isomer is attributed
to –

(A) Its ability to form intra-molecular hydrogen bonds

(B) Its ability to form inter-molecular hydrogen bonds

(C) Its ability to dissociate on heating

(D) Weak dipole-dipole interaction between molecules

55. Phenol is less acidic than :

(A) Acetic acid (B) p-methoxyphenol

(C) p-nitrophenol (D) Both A and C

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
56. The order of reactivity of the following alcohols

CH3 CH3
F
F OH OH

(I) (II)

CH3 CH3

OH Ph OH

(III) (IV)

towards conc. HCI is –

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

57. Among the following compounds, the strongest acid is –

(A) HC º CH (B) NH3 (C) CH2 = CH2 (D) CH3OH

58. Which is strongest acid -

(A) Ortho iodo benzoic acid (B) Ortho bromo benzoic acid

(C) Ortho chlorobenzoic acid (D) Ortho fluro benzoic acid

59. (CH3)3CCH2COOH is more acidic than (CH3)3SiCH2COOH because –

(A) Size of Si is more than that of carbon

(B) Electronegativity of carbon is less than that of silicon

(C) Silicon is more electropositive than carbon due to which (CH3)3SiCH2COO¯

becomes less stable

(D) None of the above

60. Peroxyacetic acid (CH3CO3H) is weaker acid than acetic acid (CH3CO2H) since –
O
||
(A)Negative charge in CH3–C –O–O– can’t be delocalised into the carbonyl
group

(B) CH3 group in CH3CO3H show +I effect

(C) Both are correct

(D) None is correct

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
61. For the following acids –

(CH3)3CCH2CO2H (CH3)3NCH2CO2H CH3COOH

(I) (II) (III)

pKa value will be in order –

(A) I > II > III (B) I < II < III

(C) I > III > II (D) II > III > I

62. Place the following in the correct order of acidity

CH º C – COOH; CH2 = CH – COOH; CH3CH2COOH

(I) (II) (III)

(A) I > II > III (B) III > II > I

(C) II > I > III (D) I > III > II

63. Phenol is a weaker acid than acetic acid because–

(A) Phenoxide ion is better stabilized by resonance than acetate ion.

(B) Acetate ion is better stabilized by resonance than Phenoxide ion.

(C) Phenol is less soluble in water than acetic acid.

(D) Both phenoxide ion and acetate ion are stable.

64. Which aromatic acid among the following is weaker than simple benzoic acid ?

COOH COOH COOH COOH

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

Cl NO2 CH3 SO3H

65. Which of the following would be expected to be most highly ionised in water?

(A) CH3CH2CH2COOH (B) CH3CHClCH2COOH

(C) CH3CH2CCl2COOH (D) CH3CH2CHClCOOH

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
66. Assign number 1 for least to 4 for most to indicate the relative base strength of
the following–

I II

C6H5NH2 p–NO2C6H4NH2

III IV

m–NO2C6H4NH2 p–CH3OC6H4NH2

I II III IV

(A) 3 1 2 4

(B) 1 2 3 4

(C) 2 3 4 1

(D) 4 1 3 2

67. Highest value of pKb will be of–

(A) NH3 (B) (CH3)2NH (C) (CH3)3N (D) CH3NH2

68. Amines are basic in nature because–

(A) They produce OH¯ ions when treated with water

(B) They have replaceable H atoms on N atoms

(C) They have lone pair of electron on N atom

(D) Both (A) & (C)

➢ STRUCTURAL ISOMERISM

69. Acetamide is isomer of -

NH2
(A) 1-amino ethanol CH3–CH–OH
(B) Formamide H–C–H
O
(C) Ethyl amine C2H5NH2
(D) Acetaldehyde oxime CH3–CH=N–OH

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

70. 2-chlorobutane & 3-chlorobutane are -

(A) Positional isomers (B) Chain isomers
(C) Geometrical (D) None of these
71. An alkane forms isomers if it possess minimum no. of carbon atoms -
(A) 1 (B) 2 (C) 3 (D) 4
72. Which of the following are isomers -
(A) Ethanol and ethoxy ethane (B) Methanol and methoxy methane
(C) Propanoic acid and ethyl acetate (D) Propionaldehyde and acetone
73. Rearrangement reaction converts any compounds into -
(A) Higher homologue (B) Lower homologue
(C) Isomers (D) Uncertain
74. Alkynes are isomers of -
(A) Cycloalkane (B) Alkadiene
(C) Alkene (D) All of the above
75. CH3–CH2–CHO & CH2=CH–CH2OH are -
(A) functional isomer (B) tautomers
(C) position isomer (D) metameres
76. Which of the following compounds can exhibit tautomerism?
CHO COCH3
(A) (B)

CHO CH3
(C) (D) CH3 C CH3
CH3

77. C7H7Cl shows how many benzenoid aromatic isomers ?

(A) 4 (B) 3 (C) 5 (D) 6

78. How many cyclic structural isomers of C4H7Cl is possible -

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

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
79. Which of the following has incorrect relation
Me
Pr Pr
(A) & identical
Me

Me Et
(B) positional
&
Pr Pr isomers

Et Et
(C) positional
&
Pr isomers

Pr
Me
Me Et
(D) & Homologues
Pr

80. Which of the following order is correct ?

COOH
OCOH
& functional isomer

OMe OEt
Et
& metamers
Me
CH2–CH2–OH CH2–O–CH3

& metamers

Me–N–Me CH2–NH–CH3

functional
&
isomers

(A) TFTF (B) FTTF (C) TTFT (D) TFFT

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
81. The type of isomerism observed in urea molecules is

(A) Chain (B) Position (C) Geometrical (D) Functional

82. How many structural formula are possible when one of the hydrogen is replaced

by a chlorine atom in anthracene ?

(A) 3 (B) 7 (C) 4 (D) 6

83. Which of the following cannot be written in an isomeric form ?

(A) CH3–CH(OH)–CH2–CH3 (B) CH3–CHO

(C) CH2=CH–Cl (D) Cl–CH2CH2–Cl

84. Only two isomeric monochloro derivatives are possible for (excluding stereo)

(A) n-butane (B) 2,2-dimethylpentane

(C) benzene (D) neopentane

➢ GEOMETRICAL ISOMERISM

85. The Z-configuration in the following is -

H C2 H 5 C3H7 H F Cl H Br
(A) C=C (B) C=C (C) C=C (D) C=C
CH3 C3 H 7 C2 H 5 CH3 H Br F F

86. An alkene exists as geometrical Isomers. The minimum number of carbon atoms
in the molecules is -
(A) 1 (B) 2 (C) 3 (D) 4

87. Which of the following cannot show geometrical isomerism ?

(A) CH3CH = CHC2H5 (B) (CH3)2 C = CHC2H5

(C) CH3CH = CHCH3 (D) All the three

88. Which of the following is not true for maleic acid and fumaric acids.
(A) Configurational isomers (B) Stereo isomers
(C) Z and E isomers (D) Optical isomers

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

89. Which of the following will not show cis-trans isomerism ?

(A) Butanedioic acid (B) 1,2-dimethyl cyclopropane
(C) 1,2-dichloroethene (D) Butene dioic acid
90. Which type of isomerism can not be shown by benzaldoxime ?
(A) Optical isomerism (B) Functional group isomerism
(C) Geometrical isomerism (D) Configuration isomerism

91. CH3 C Cl is -

Cl C Br
(A) trans (B) Z (C) both correct (D) none

➢ CONFORMATIONAL ISOMERISM

92. How many conformations does ethane have?

(A) 1 (B) 2 (C) 3 (D) Infinite

93. The correct energy gradation of different conformers is -

(A) Staggard > skew > eclipsed (B) Skew > staggard > eclipsed
(C) Eclipsed > skew > staggard (D) Skew > staggard > eclipsed

94. Most stable form of cyclohexane is -

(A) Boat (B) Chair (C) Skew (D) eclipsed

95. When temperature is increased -

(A) % of eclipsed form increses (B) % of skew form increases
(C) % of staggered form increases (D) No effect on any form

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

➢ OPTICAL ISOMERISM

CH3
H Cl
96. If optical rotation produced by is + 36º then that produced by
Cl H

CH3
CH3
H Cl
is -
H Cl

CH3
(A) – 36º (B) 0º (C) + 36º (D) Unpredictable

97. Which of the following compounds can not exist as enantiomers -

H
(A) CH3–CH(OH) COOH (B) CH3–CH2–C–CH2OH
CH3
(C) C6H5CH2–CH3 (D) C6H5CHClCH3
98. Meso tartaric acid is optically inactive due to presence of -
(A) plane of symmetry (B) molecular asymmetry
(C) external compensation (D) two asymmetric carbon atoms

99. Which of the following compound is optically active ?

(A) CH3CH2OH (B) (CH3)2CHCH2OH
(C) CH3CHOHC2H5 (D) CCl2F2
100. Chiral molecules are those which are -
(A) superimposable on their mirror image
(B) not superimposable on their mirror image
(C) unstable molecules
(D) capable of showing geometrical isomerism
101. d-and -forms of an optically active compound differ in -

(A) boiling points (B) melting points

(C) specific rotation (D) specific gravity

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
102. The optically active tartaric acid is named as D- (+)-tartaric acid because it has
a positive
(A) optical rotation and is derived from D glucose
(B) pH in organic solvent
(C) optical rotation and is derived from D-(+) glyceraldehyde
(D) optical rotation only when substituted by deuterium

103. Molecular formula C5H10O can have -

(A) 6-Aldehyde, 4-Ketone (B) 5-Aldehyde, 3-Ketone

(C) 4-Aldehyde, 3-Ketone (D) 5-Aldehyde, 2-Ketone
CH3
HO H
104. The full name of the compound is
H Cl

C2H5
(A) (2R, 3S)-3-chloro-2-pentanol
(B) (2R, 3R)-3-chloro-2-pentanol
(C) (2R, 3R)-3-chloro-2-pentanol
(D) (2R, 3S)-3-chloro-2-pentanol
105. How many stereoisomers can exist for the following acid?
H–C(OH)CO2H
H–CCO2H
H–C(OH)CO2H
(A) Two (B) four (C) Eight (D) Sixteen

106. The R/S configuration of these compounds are respectively -

H
HO H NH2
CF3 HS
COOH

H CH3
CHO

(A) R, R, R (B) R, S, R (C) R, S, S (D) S, S, S

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
107. When an optically active compound is placed in a 10 dm tube is present 20 gm
in a 200 ml solution rotates the PPL by 30º. Calculate the angle of rotation and
specific angle of rotation if above solution is diluted to 1 litre.
(A) 16º and 36º (B) 6º and 30º (C) 3º and 30º (D) 6º and 36º

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Level-2

1. Consider the following amines:

(1) C6H5−NH2 (2) o−NO2−C6H4−NH2

(3) m−NO2−C6H4−NH2 (4) p−NO2−C6H4−NH2

Arrange these compounds in decreasing order of basicity:

(A)(1) > (2) > (3) > (4) (B) (2) > (1) > (3) > (4)

(C) (1) > (3) > (4) > (2) (D)(1) > (3) > (2) > (4)

2. Weakest base among the following amino compounds is:

(A) NH (B) NH NH

(C) NH2 (D) N

3. Most acidic hydrogen is present in:

O O O

(A) (B)

(C) (CH3CO)3CH (D)(CH3)3COH

4. Which nitrogen in Lysergic acid diethylamide (LSD) is most basic?

(1) O
(3)
H−N
(2) C−N(C2H5)2
N
CH3

(A)1 (B) 2

(C)3 (D)All are equally basic

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
5. Which of the following carbanion is most stable?

CH2 CH2
NO2
(A) (B)

NO2

CH2 CH2
CN
(C) (D)

CN

6. Which one of the following compound is most acidic?

(A)HO−CH2−COOH (B) O2N−CH2−COOH

(C)Cl−CH2−COOH (D)NC−CH2−COOH

7. Arrange homolytic bond energies of C−H bonds designated by (I), (II), (III), (IV)
and (V) in increasing order.

(II)
(V) H (I)
H H

(III)
H
CH2−H
(IV)

(A)(II) < (V) < (IV) < (III) < (I) (B) (III) < (V) < (IV) < (II) < (I)

(C)(I) < (III) < (IV) < (II) < (V) (D)(II) < (IV) < (V) < (I) < (III)

8. Consider the following three halides

(a) CH3−CH2−Cl (b) CH2=CH−Cl (c) HCC−Cl

Arrange these three compounds in decreasing order of C−Cl bond length.

(A)(a) > (b) > (b) (B) (c) > (b) > (a)

(C)(b) > (c) > (a) (D)(a) > (c) > (b)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
9. Arrange basicity of the given compounds in decreasing order.

(a) CH3−CH2−NH2 (b) CH2=CH−NH2 (c) CHC−NH2

(A)(a) > (b) > (c) (B) (a) > (c) > (b)

(C) (c) > (b) > (a) (D)(b) > (c) > (a)

10. Which of the following is a non−aromatic compound/species?

(a) (b)

(c) (d)


(A)(a) (B) (b)

(C)(c) (D)(d)

11. Arrange stability of given compounds in decreasing order

(1) C6H6 (2) CH2=CH−CH2−CH2−CH=CH2

(3) CH2=CH−CH=CH2 (4) CH2=C=CH2

(A)(3) > (1) > (4) > (2) (B) (1) > (3) > (2) > (4)

(C) (1) > (3) > (4) > (2) (D)(3) > (1) > (2) > (4)

12. The most stable free radical is

Me

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

13. According to the Huckel’s rule, which of the following species will be aromatic?


(I) (II) (III) (IV)


(A)(I) (B) (II)

(C)(III) (D)(IV)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

14. Which of the following compound is most acidic?

OH
NO2
(A) OH (B)

OH OH

(C) (D)
NO2
NO2

15. Which of the following carbocation is most stable?

 
(A) (CH3 ) 2 CH (B) (CH3 ) 3 C

 
(C) Ph − CH − CH3 (D) Ph − CH2
•

16. In (t−Bu)3C , the hybridization of central carbon atom is

H
(A)sp (B) sp2

(C)sp3 (D)none of these

17. The cyclopentadienyl cation, is

(A)aromatic (B) anti−aromatic

(C) non−aromatic (D)none of these

18. Which one of the following compound would you expect to be the strongest
carbon acid?

O
(A)CH2(COOC2H5)2 (B)

O O
(C)CH3COCH2COOC2H5 (D)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
19. Which of the following species cannot function as an electrophile?

..
(A)H3C (B) CCl2

(C)SiF4 (D)H3O

20. Which of these species is capable of acting as electrophile?

(A)CO2 (B) CH3−C−H

O

(C)AlCl3 (D)All of these

21. Which one of the following reactions leads to the formation of carbanion as an
intermediate?
−
C N; polar h
(A)R−Cl ⎯⎯ ⎯⎯→ ? (B) R−H + X2 ⎯⎯→ ?
protic solvent

(C) R−CH=CH2 + H ⎯→ ? (D)CH3−NO2 + B ⎯→ ?

22. Which one of the following is an anti-aromatic species?

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

.. ..
 .. 

23. Which one of the following reaction intermediates is not electrophilic in

character?

(A)Carbocation (B) Carbanion

(C) nitrenes (D)Carbenes

24. A compound/species is anti−aromatic when it has

(A)4n −electrons (B) (4n + 1) −electrons

(C) (4n + 2) −electrons (D)(4n + 3) −electrons

25. The cyclopropenyl cation,  is

(A)aromatic (B) anti−aromatic

(C) non−aromatic (D)non planar

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
26. Identify the species not capable of acting as an electrophile.

(A)BCl3 (B) AlCl3

(C) NH+4 (D)CO2

27. Which of the following species is a nucleophile but not an electrophile?

 
(A) NH 4 (B) NH 3− OH

(C) H3O (D) CH3−C−CH3

O

28. Which is the most stable carbocation?


(A)(CH3)2CH+ (B) CH2

(C) CH2 = CH − CH2+ (D)(CH3)3C+

29. Steric inhibition of resonance can be expected in

(A) N (B) N

(C) N (D) N

30. Which free radical is the most stable one?

•
•
(A) CH2 (B) CH2

CH3
• •
(C) (CH3)3C (D)(CH3)2CH

31. Which of the following represents the correct order of acidic strength?

(A)HCO2H > CO2H−CO2H (B) CH3CO2H > HCO2H

(C)CO2H−CO2H < CO2H−CH2−CO2H (D)CO2H−CO2H > HCO2H

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
32. Which one of the following intermediate is electrically neutral?

(A)Carbanion (B) Benzyne

(C) Carbon free radical (D)Carbocation

33. Which one of the following is an incorrect statement?

(A)Aniline shows stronger resonance than phenol.

(B) 2,6−dimethyl−4−nitrophenol is more acidic than 3,5−dimethyl−4−nitrophenol.

. .
(C)CH2−CH=CH−CH2 is a valid resonance structure of CH2=CH−CH=CH2.

(D)Benzyl free radical is more stable than t−butyl free radical.

34. In which of the following molecule, the group attached to benzene does not show
any type of resonance effect?


(A) NH2 (B) NH3

(C) OH (D) Cl

35. Which of the following is correct order regarding the acidity of carboxylic group?

(A)CH3CH2CH(Cl)COOH > CH3CH(Cl)CH2COOH > ClCH2CH2CH2COOH

(B) CH3CH2CH(Cl)COOH < CH3CH(Cl)CH2COOH < ClCH2CH2CH2COOH

(C)CH3CH2CH(Cl)COOH > CH3CH(Cl)CH2COOH < ClCH2CH2CH2COOH

(D)CH3CH2CH(Cl)COOH < CH3CH(Cl)CH2COOH > ClCH2CH2CH2COOH

36. Which of the following is correct order regarding −I effect of the substituents?

(A)−NH2 > −OH > −F (B) −NH2 < −OH < −F

(C)−NH2 > −OH < −F (D)−NH2 < −OH > −F

37. Which of the following order is not the correct order regarding −I effect of the
substituents?


(A)−I < −Cl < −Br < −F (B) −NR2 < − O R 2


(C) −NR2 < −OR < −F (D)−SR < −OR < − OR 2

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
38. Which of the following is correct order regarding the acidity of carboxylic acids?

(A)(CH3)3CCOOH > (CH3)2CHCOOH > CH3CH2COOH

(B) (CH3)3CCOOH > (CH3)2CHCOOH < CH3CH2COOH

(C)(CH3)3CCOOH < (CH3)2CHCOOH > CH3CH2COOH

(D)(CH3)3CCOOH < (CH3)2CHCOOH < CH3CH2COOH

39. Which of the following compound has the highest pKa value?

OH OH
Cl NO2
(A) (B)

OH OH
CH3 OCH3
(C) (D)

40. Which is the most stable singlet carbene among the following?

.. ..
(A)CF2 (B) CCl2

.. ..
(C) CBr2 (D)CI2

41. Which of the following nitrogenous base is the strongest in water?

(A) (B)
N N
H H

(C) (D)
N N
H

42. In which one of the following compounds delocalisation is not possible?

(A)2−butene (B) 1,3−butadiene

(C)1,3,5−hexatriene (D)Benzene

43. Consider the following carbocations:

 
(1) CH3−CH2 (2) CH2=CH

 
(3) CH2=CH−CH2 (4) C6H5−CH2

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Stability of these carbocations in decreasing order is
(A)(4) > (3) > (1) > (2) (B) (4) > (3) > (2) > (1)

(C) (3) > (4) > (2) > (1) (D)(3) > (4) > (1) > (2)

44. Which one of the following cation is most acidic?

   
NH3 NH3 NH3 NH3

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

OH NO2 CH3

45. Decreasing order of stability of given carbocations is



(1) (2) CH2=CH−CH2

 
(3) C6H5−CH2 (4) CH3−CH−CH3

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

46. How many pairs of diastereoisomers are possible in the following molecule
PhCH(Cl)CH(Cl)Ph?

(A)one (B) two

(C)four (D)eight

47. Which of the following compound will show optical isomerism?

(A)Butanal (B) 2−Chlorobutanol

(C) 2−Propanol (D)1−Butene

48. The total number of optically active and meso forms possible for the compound
[HOOC−(CH(OH))3 − COOH] respectively are

(A)4, 4 (B) 2, 2

(C) 3, 2 (D)2, 3

49. The most stable conformation of chlorohydrin at room temperature is

(A)fully eclipsed (B) partially eclipsed

(C) gauche (D)staggered

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
50. The dihedral angles between the two C−Br bonds in gauche, partially eclipsed,
staggered and fully eclipsed conformations of 1,2−dibromoethane respectively
are

(A)60°, 120°, 180°, 0° (B) 0°, 60°, 120°, 180°

(C)120°, 60°, 180°, 0° (D)60°, 0°, 180°, 120°

51. Which of the following statement is false about cyclopropane−1,2−dicarboxylic

acid?

(A)It has two geometric isomers.

(B) It has three stereoisomers.

(C) All the stereoisomers are optically active.

(D)Only trans−isomer shows enantiomorphism.

52. The IUPAC name of Cl3C.CHO is

(A)Trichloroacetaldehyde (B) 1,1,1−Trichloroethanal

(C) 2,2,2−Trichloroethanal (D)Chloral

53. The name of CH CH is

CHO NH2

(A)1−Aminoprop−2−enal (B) 3−Aminoprop−2−propenal

(C) 1−Amino−2−formylethene (D)3−Amino−1−oxoprop−2−ene

54. IUPAC name of the compound

BrCH2−CHCl−CHCl2 is
(A)1−Bromo−2,3,3−trichloropropane (B) 1,1,2−Trichloro−3−bromopropane

(C) 3−Bromo−1,1,2−trichloropropane (D)None of these

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
55. Indicate the wrongly named compound.

(A) CH3−CH−CH2CH2CHO (B) CH3−CH−CC−COOH

CH3 CH3
(4−Methylpentanal) (4−Methyl−2−pentynoic acid)

O
(C) CH3CH2CH2−CH−COOH (D) CH3CH2−CH=CH−C−CH3
(3−Hexen−2−one)
CH3
(4−Methylpentanoic acid)

56. Which of the following compound is not chiral?

(A)DCH2CH2CH2Cl (B) CH3CH(D)CH2Cl

(C) CH3CH(Cl)CH2D (D)CH3CH2CH(D)Cl

57. Which of the following compound exhibit geometrical isomerism?

(A)CH2=CClBr (B) CH3CH=CClBr

(C) CH3CH=CCl2 (D)(CH3)2C=CClBr

58. Which of the following compound will show metamerism?

(A)CH3−O−COC3H7 (B) CH3−S−C2H5

(C) CH3−O−CH3 (D)CH3−O−C2H5

59. Which one of the following compound will not exhibit optical isomerism?

(A)CH3CH(OH)Br (B) CH3CH(OH)CH3

Br CH3
(C) CH3CH2−CH−CH−CH3 (D) CH3−CH−CH−CH2OH
OH Br

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
60. What type of isomerism is shown by the following compounds?

O
OH
(A)Metamerism (B) Positional

(C) Functional (D)Tautomerism

61. Which of the following statements regarding the molecule CH 2=C=CH2 is not
correct?

(A)Both the two −bonds are present in the same plane.

(B) The central carbon atom is sp hybridized while the terminal atoms are sp 2
hybridized.

(C) The molecule is non-linear.

(D)The molecule contains six −bonds and two −bonds.

62. If two compounds have the same empirical formula but different molecular
formulae they must have

(A)different percentage composition (B) different molar mass

(C) same viscosity (D)same vapour density

63. The IUPAC name of the compound is CH3

HO CH3

(A) 1,1−dimethyl−3−hydroxycyclohexane

(B) 3,3−dimethyl−1−hydroxycyclohexane

(C) 3,3−dimethyl−1−cyclohexanol

(D) 1,1−dimethyl−3−cyclohexanol

64. The compound which is not isomeric with diethyl ether is

(A) n−propyl methyl ether (B) 1−butanol

(C) 2−methyl−2−propanol (D) butanone

65. The maximum number of structural isomers (alkene) with the molecular formula C4H8
is
(A) 2 (B) 3
(C) 4 (D) 5

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

66. The number of isomers of dibromoderivative (molar mass 186 g mol−1) of an alkene is
(A) two (B) three
(C) four (D) six
67. The number of optically active isomers of C3H5Br3 is
(A) 1 (B) 2
(C) 3 (D) 4
68. The enolic form of acetone contains
(A) 9 sigma bonds, 1 pi bond and 2 lone pairs
(B) 8 sigma bonds, 2 pi bond and 2 lone pairs
(C) 10 sigma bonds, 1 pi bond and 1 lone pairs
(D) 9sigma bonds, 2 pi bond and 1lone pairs
69. The compound

CH3 H
C=C
Cl (CH2)4−CH(OH)−CH3

will have
(A) 4 geometrical isomers (B) 2 geometrical isomers only
(C) 2 optical isomers (D) 4 stereoisomers
70. Which of the following statements is not correct?
(A) A meso compound has chiral centres but exhibits no optical activity.
(B) A meso compound has no chiral centres and thus are optically inactive.
(C) A meso compound has molecules which are superimposable on their mirror
images even though they contain chiral centres.
(D) A meso compound is optically inactive because the rotation caused by one half of
a molecule is cancelled by an equal and opposite rotation caused by the other half
of the same molecule that is the mirror image of the first.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

71. 1, 2−dimethyl cyclohexane has

(A) 2 geometrical isomers and no optical isomers.
(B) 2 optical isomers and no geometrical isomers.
(C) 3 stereoisomers.
(D) none of these.
72. The most stable configuration of ethylene glycol is
(A) anti (B) gauche
(C) partially eclipsed (D) fully eclipsed
73. The compound, C2FClBrI has

(A) 4 geometrical isomers (B) 6 geometrical isomers

(C) 4 optical isomers (D) (B) and (C) both

74. Total number of optical isomers of COOH−(CHOH)2COOH is

(A) 2 (B) 3
(C) 4 (D) 6

75. For the compound, total number of optical isomers will be

(A) 2 (B) 4
(C) 8 (D) 16
76. CH3COCH2COCH3 shows tautomerism, which one of the following will not show?
O O

(A) (B)

O
O O
CH2CN
(C) (D)

77. In which compound, the enol form will be maximum in n−hexane?

(A) CH3COCH2CO2C2H5 (B) CH3COCH2Cl

(C) CH3COCH2COCH3 (D) PhCOCH2COCH3

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
78. Total number of isomeric alcohols with the molecular formula C4H10O is
(A) 2 (B) 3
(C) 4 (D) 5
79. (+) Mandelic acid has a specific rotation of +158°. What would be the observed specific
rotation of the mixture of 25% (−) mandelic acid and 75% (+) mandelic acid?

(A) +118.5° (B) −118.5°

(C) −79° (D) +79°

80. The total number of isomers possible for trisubstituted C6H3Br2Cl is
(A) Six (B) Four
(C) Three (D) Two
81. In the following sequence of standard stereochemical Fischer formulae, indicate the
one that may be identical with the given compound.
NH2

H CH3

CO2H

CO2H NH2 H COOH

(A) H CH3 (B) H3C H (C) H2N CH3 (D) H3C H

NH2 COOH COOH NH2

82. Which of the follower stereoisomer exhibits a plane of symmetry?

COOH
Br
CH3 H
(A) (B)
H 
H CH3 AsMe3 NO2

OH
H COOH Ph
(C) (D)
HOOC H H
OH

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
83. Which of the Newmann projections shown below represents the most stable
conformation about the C1–C2 bond of 1-iodo-2-methylpropane?
H3C I CH3
H I
(A) (B)
H
H CH3 H CH3
H
H

CH3 H3C H
I H
(C) (D)
I
H CH3 H CH3
H
H

84. Meso tartaric acid and (+)−tartaric acid are

(A) position isomers (B) diastereomers
(C) enantiomers (D) racemic mixture
85. Which of the following compound will show geometrical isomerism?
Cl
(A) (B) CH3CH=NOH
Cl

(C) (D) all of them

86. How many structural isomers of a hydroxy acid of formula C4H8O3 show optical
activity?
(A) 2 (B) 3
(C) 4 (D) 5
87. Which of the following compound having molecular formula C7H16 will show optical
isomerism?
(A) 2, 3-dimethyl pentane (B) 2, 2-dimethyl pentane
(C) 2-methyl hexane (D) none of these

88. At room temperature the eclipsed and the staggered forms of ethane cannot be
isolated because
(A) both the conformers are equally stable.
(B) they interconvert rapidly.

(C) there is a large energy barrier of rotation about the -bond.

(D) the energy difference between the conformers is large.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

89. The following compound shows

H3C H
C=C H
H3C C
H3C COOH
(A) optical isomerism only (B) geometrical isomerism only
(C) optical and geometrical isomerism (D) metamerism only

90. n−Heptane on monochlorination gives a number of isomers. How many of them are
optically active?
(A) 1 (B) 2
(C) 3 (D) 4

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Level-3

(More than one Option Correct Question)

1. The correct order of the stability of the given resonating structures

 
CH2−CH−CH=CH−OCH3 CH2−CH=CH−CH=O−CH3
(I) (II)
 
CH2=CH−CH−CH−OCH3 CH2=CH−CH−CH=O−CH3
(III) (IV)
(A)(IV) > (II) > (I) > (III) (B) (IV) < (II) < (III) < (I)

(C)(III) < (I) < (II) < (IV) (D)(I) > (III) > (II) > (IV)

2. Which of the following compound shows +R effect on benzene ring?

O
NH−C−CH3 O−CH3 C(CH3)3 O

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

(a) (b)
HO2C CO2H
3. The correct acidity order of the indicated groups in the

NH3
(c)

following compound is

(A)(b) > (a) > (c) (B) (a) < (b) < (c)

(C) (c) > (b) > (a) (D)(c) < (a) < (b)

4. Which of the following is true about carbenes?

(A)Carbenes can be formed by −elimination of CHCl3.

(B) Carbenes can do nucleophilic attack.

(C) Among alkylated carbenes, singlet form is more stable than triplet form.

(D)Carbenes can undergo addition to double bond to give cyclopropyl systems.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
5. In which of the following molecules all the effects namely inductive, mesomeric
and hyperconjugation operate:

(A) Cl (B) COCH3

CH3

(C) CH3 (D)CH3−CH=CH−Cl

CH3

6. is more basic than because

..
N
.. N
H

(A) is a six membered aromatic ring.

N
..

(B) Lone pair of is not taking part in delocalization.

N
..

(C)Lone pair of is taking part in delocalization.

..
N
H

(D) is an aromatic amine.

..
N
H

7. Which of the following compound/species is/are aromatic species?

O
(A) (B)


O

(C) (D)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
8. Which of the following represent(s) correct order of acidity?

(A)CHF3 > CHCl3 (B) CHCl3 > CHF3

(C) > (D) >

O O S S S S O O

9. Which of the following intermediate is aromatic in nature?

CH3


(A) (B) (C) : (D) (singlet)
..

10. In which of the following pairs, first member is more stable than the second?

• • .
(A) (C 6H5 ) 3 C , (C 6H5 ) 2 C CH3 (B) :CH2, CH2
.
• •

(C)(C6H5)3C: , :CH3 (D) (C 2H5 ) 3 C, (CH3 ) 3 C

11. Which of the following compounds on dichlorination gives 3 different products

(may not occur by same mechanism in all compounds and even low yield
products are to be counted).

(A) (B)

CH3

(C) (D)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
12. Which of the following pairs represents enantiomers?

NH2 H CH3 OH
H OH H3C H
(A) H3C H , HO2C CH3 (B)
H Cl , H CH3
CO2H NH2 CH3 Cl

CH3 H NH2 CH3

H OH H3C OH H CO2H CO2H H
(C) (D) , HO
H Cl , H3C Cl H OH H
CH3 H CH3 NH2

13. Which of the following compounds show position as well as metamerism?

(A) CH3CH2−C−CH2CH3 (B) CH3−O−CH2−CH2CH3

O

(C)CH3CH2CH2CHO (D)CH3CH2NH2

14. Which of the following compounds have gauche conformer less stable than
staggered conformer?

(A)CH3−CH3 (B) FCH2−CH2OH

(C) CH3−CH2−CH2−CH3 (D)CH3COOCH2−CH2−OCOCH3

15. Which of the following compounds are optically active?

CH3
CH2OH
H Cl
(A) H Cl (B) HO H
CH3 CH3

CCl3
COOH
H OH
(C) H3C CH2Cl (D) HO H
COOH CCl3

16. Keto-enol tautomerism is observed in

(A)C6H5CHO (B) C6H5COCH3

(C)C6H5COC6H5 (D)C6H5COCH2COCH3

17. Which of the following compounds are the pair of structural isomers?

(A)(CH3)2CHOC2H5 ; CH3(CH2)2OC2H5 (B)CH3CH2NO2 ; CH2(NH2)COOH

(C)(CH3)2CH(CH2)2CH3 ; CH3(CH2)2CH(CH3)2 (D) CH3CH2CO2H ; CH3CO2CH3

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
CH3
18. CH3−CH−CH2CH2CH3 on monochlorination with Cl2 in the presence of light at
room temperature (reaction proceeds by free radical mechanism) gives ‘p’
isomers. The product mixture on fractional distillation gives ‘q’ fractions. Which
of the following option is correct?

(A)‘p’ is 8 (B) ‘p’ is 7

(C)‘q’ is 4 (D)‘q’ is 5

19. Which of the following compounds/isomers have centre of symmetry?

NO2 Me3C
O
CO2Et
(A) (B)
EtO2C
CMe3 NO2 O
(trans isomer)

CH3
CH3
H3C H
H OH
(C) H
H (D)
HO H
H CH3
CH3
CH3

20. A racemic mixture of C2H5−CH−CO2H can be resolved by reacting with

CH3

(A) C2H5−CH−OH (B) C2H5−CH−NH2

CH3 CH3

(C)CH3−CH−NH2 (D) CH3−CH−OH

CH3 CH3

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
MATCH THE FOLLOWING

1.
Column I Column II

I. O
HIO4
(A) Aromatic product

K
II. (B) Non-aromatic product

AgNO3
III. Cl (C) Precipitates are formed

Br
IV. AgBF4 (D) No precipitation

(E) (4n + 2)  electrons in the product.

2.

Column I Column II

CH3 CH3
H Br Br H
I. H Br and Br H (A) Both meso compound
C2H5 C2H5
CH3 CH3
H Br Br H
II. H Br and H Br (B) Enantiomers
CH3 CH3
COOH COOH
H OH
III. H OH and HO H
(C) Both chiral
HO H
COOH COOH
H3C CH3
IV. C=C
H3C H (D) Diastereomers
and C=C
H H H CH3
(E) Atleast one of them achiral.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

Assertion & Reasoning:

Directions: Read the following questions and choose
(A) If both the statements are true and statement-2 is the correct explanation
of statement-1.

(B) If both the statements are true but statement-2 is not the correct
explanation of statement-1.

(C) If statement-1 is True and statement-2 is False.

(D) If statement-1 is False and statement-2 is True.

1. Statement-1: The basic strength of amines in an aqueous solution is (CH3)2NH >

CH3NH2 > (CH3)3N > NH3.

Statement-2: The basic strength of amines in aqueous solution is governed by

the availability of electron pair on nitrogen as well as on the
solvation of their conjugate acids.

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

2. Statement-1: The o−hydroxy benzoic acid is a stronger acid than o−methoxy

benzoic acid.

Statement-2: The ortho effect is more prominent in o−hydroxy benzoic acid than
in o−methoxy benzoic acid.

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

3. Statement-1: Phenoxide ring is more activated than phenol ring towards

electrophilic substitution reaction.

Statement-2: −O− group shows +I effect while −OH group shows −I effect. +R
effect is shown by −O− as well as −OH group.

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

4. Statement-1: Maleic acid is a weaker acid than fumaric acid towards first
ionization.

Statement-2: Conjugate base of maleic acid is stabilized by intramolecular

hydrogen bonding but not the conjugate base of fumaric acid.

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

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
5. Statement-1:7−bromo−1,3,5−Cycloheptatriene ionizes more readily than
5−bromo−1−3−cyclopentadiene.
Statement-2: Cycloheptatrienyl cation is more stable than cyclopentadienyl
cation due to aromatic character of the former.

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

6. Statement-1: Keto form of aceto−acetic ester is more stable than its enolic form.

Statement-2: Enolic form of aceto−acetic ester is stabilized by intramolecular

hydrogen bonding.

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

7. Statement-1: Extent of enolization depends upon the solvent used.

Statement-2: If the solvent used makes hydrogen bonding with carbonyl group,
it decreases the enol content.

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

8. Statement-1: Oxime of acetone does not show geometrical isomerism.

Statement-2: Both the isomers have different configurations around double

bond.

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

9. Statement-1: o,o–Disubstituted biphenyls may exhibit optical isomerism.

Statement-2: If the o,o–substituents are very bulky even then there is no loss of
planarity of the biphenyl rings.

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

10. Statement-1: Racemic mixture and meso forms are optically inactive.
Statement-2: These are optically inactive due to external and internal
compensation respectively.

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

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet

Comprehension – 1 : (Question No. 1-4)

Planar monocyclic rings containing (4n + 2) −electrons (where n = 0, 1, 2, 3, and

so on), should be aromatic. This is known as Huckel
 ' s rule for aromaticity.
Applying this rule, benzene and its derivatives have six delocalised electrons and
n = 1.

Thus to be aromatic, a molecule must have 2(n = 0), 6(n = 1), 10(n = 2) etc. −
electrons in a closed −orbital loop. Another requirement for aromaticity is
planarity of the ring. If the ring is not planar, overlap of p−orbitals is diminished
or prevented, then compound will not be aromatic.
Derivatives of benzene are aromatic as they fulfill both the conditions. Molecules
having two or more benzene rings fused together are called polycyclic
benzenoid aromatic hydrocarbons. For example, naphthalene, anthracene etc.

Non−benzenoid aromatic compounds are those which contain a ring that is not
six membered. Examples of such compounds are cyclopentadienyl anion,
cyclopropenium cation, tropylium cation etc. Cyclic conjugated compounds,
which possess only 4n electrons, do not satisfy the Huckel rule and are anti−
aromatic in nature. In a reaction the reactant would tend to react with reagents that
can result into aromatic products / salts.

1. Which of the following is the correct option regarding the direction of the dipole
moment?

(A) (B)

(C) (D)

2. Which of the following is the correct statement?

(A) gives immediate turbidity with aqueous AgNO3.

Br

(B) Br gives an immediate turbidity with aqueous AgNO3.

(C)Both of them give immediate turbidity with aqueous AgNO3.

(D)None of them give any turbidity with aqueous AgNO3.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
3. Which of the given statement is correct?

(A) is more acidic than CH2=CH−CH2−CH=CH2

(B) is more acidic than

(C)Both (A) and (B) are correct.

(D)None of the given option is correct.

4. Which of the given reaction is correct?


(A) O + HBr ⎯→ OH
Br−

OH
(B) O + HBr ⎯→
Br

(C)
Ph Ph Ph Ph
+ HClO4 ⎯→  ClO4
O OH

(D)Both (A) and (C) are correct.

Comprehension – 2 : (Question No 5-9)

A bond between two carbon atoms is formed by the overlaping of sp3 hybrid
orbitals of carbon atom along their internuclear axis. It gives symmetrical
electronic distribution along the internuclear axis and thus rotation about
carbon-carbon single bond is almost free. It results in number of spatial
arrangements of atoms called conformations. In any conformation, the angle
between C–C and C–H bonds on adjacent carbon atom is known as dihedral
angle. Stability and energy of the conformations depend on the torsional strain
and Van der Waal’s strain.

The order of stability of conformations of n−butane is fully eclipsed < partially

eclipsed < skew or gauche < staggered or anti. But in some cases, skew or
gauche is stabilized by intramolecular hydrogen bonding.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Cyclic compounds also follows the same pattern. According to Baeyer strain
theory, greater the deviation from the normal tetrahedral angle, greater is the
angular strain and lesser is the stability of cycloalkane. The most commonly
found cyclic compounds usually contain six membered ring. They also show
conformations. The most stable conformation of cyclohexane is chair form
which is staggered and free from any strain.

5. Dihedral angle in staggered and fully eclipsed conformations of n−butane are

(A)120°, 0° (B) 180°, 0°

(C) 60°, 120° (D)180°, 120°

6. Which of the following molecule has the highest deviation from tetrahedral bond
angle?

(A)Cyclopropane (B) Cyclobutane

(C) Cyclopentane (D)Cyclohexane

7. The value of equilibrium constant for the equilibrium

Eclipsed form (2%) Staggered form (98%)

of ethane is

(A)49 (B) 1

(C)0.02 (D)4.9

8. For CH3−CH−CH−CH3, which conformer is the most stable?

Cl OH

(A)Anti or staggered (B) Fully eclipsed

(C)Gauche or skew (D)Partially eclipsed

9. Which of the following statement is correct?

(A)Three membered ring is more stable than a four membered ring.

(B) Six membered ring is more stable than a five membered ring.

(C) Planar six membered ring has less eclipsing strain than a planar five
membered ring.

(D)All five carbons in cyclopentane are present in the same plane.

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
ANSWERS

1. [D] 2. [D] 3. [B] 4. [B]

5. [A] 6. [B] 7. [A] 8. [A]

9. [D] 10. [D] 11. [C] 12.[C]

13. [B] 14. [A] 15. [A] 16. [A]

17. [D] 18. [B] 19. [A] 20. [D]

21. [B] 22. [C] 23. [D] 24. [A]

25. [D] 26. [C] 27. [A] 28. [D]

29. [B] 30. [C] 31. [C] 32. [D]

33. [B] 34. [B] 35. [B] 36. [D]

37. [B] 38. [D] 39. [A] 40. [A]

41. [D] 42. [A] 43. [A] 44. [D]

45. [D] 46. [B] 47. [B] 48. [B]

49. [B] 50.[D] 51. [D] 52. [C]

53. [A] 54. [A] 55. [D] 56. [C]

57. [D] 58. [A] 59.[C] 60. [A]

61. [C] 62. [A] 63. [B] 64.[C]

65. [C] 66. [A] 67. [A] 68. [D]

69. [D] 70. [D] 71. [D] 72. [D]

73. [C] 74. [B] 75. [A] 76. [B]
77. [A] 78. [A] 79. [B] 80. [C]
81. [D] 82. [A] 83. [C] 84. [A]

85. [A] 86. [D] 87. [B] 88.[D]

89. [A] 90. [B] 91. [B] 92.[D]

93. [C] 94. [B] 95.[A] 96. [B]
97. (C) 98. [A] 99. [C] 100.[B]

101. [C] 102.[C] 103. [B] 104. [B]

105. [B] 106.[A] 107. [B]

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Level-2

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

6. (B) 7. (A) 8. (A) 9. (A) 10. (D)

11. (B) 12. (D) 13. (B) 14. (D) 15. (C)

16. (B) 17. (B) 18. (B) 19. (D) 20. (D)

21. (D) 22. (D) 23. (B) 24. (A) 25. (A)

26. (C) 27. (B) 28. (D) 29. (C) 30. (A)

31. (D) 32. (B) 33. (C) 34. (B) 35. (A)

36. (D) 37. (D) 38. (A) 39. (D) 40. (A)

41. (D) 42. (A) 43. (A) 44. (C) 45. (C)

46. (B) 47. (B) 48. (B) 49. (C) 50. (A)

51. (C) 52. (C) 53. (B) 54. (C) 55. (C)

56. (A) 57. (B) 58. (A) 59. (B) 60. (C)

61. (A) 62. (B) 63. (C) 64. (D) 65. (B)

66. (B) 67. (B) 68. (A) 69. (D) 70. (B)

71. (C) 72. (B) 73. (B) 74. (B) 75. (B)

76. (B) 77. (D) 78. (C) 79. (D) 80. (A)

81. (D) 82. (D) 83. (C) 84. (B) 85. (D)

86. (B) 87. (A) 88. (B) 89. (A) 90. (B)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025

 GOC& ISOMERISM Dexter Tutorials Sheet
Level-3

1. (A, C) 2. (A, B, D) 3. (A, D) 4. (A, D) 5. (B, D)

6. (B, C) 7. (A, B, C) 8. (B, D) 9. (A, B) 10. (A, C)

11. (A, B) 12. (A, C) 13. (A, B) 14. (A, C, D) 15. (B, D)

16. (B, D) 17. (A, B, D) 18. (A, D) 19. (B, C) 20. (A,B)

MATCH THE FOLLOWING

1. I − (A), (D), (E) ; II − (A), (D), (E) ; III − (A), (C), (E) ; IV − (B), (C)

2. I − (B), (C) ; II − (D), (E) ; III − (A), (E) ; IV − (D), (E)

Assertion & Reasoning:

1. (A) 2. (C) 3. (A) 4. (D) 5. (A)

6. (D) 7. (A) 8. (C) 9. (D) 10. (A)

Comprehension Type:

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

5. (B) 6. (A) 7. (A) 8. (C) 9. (B)

WWW.DEXTERCHEM.IN GOC & ISOMERISM ADHYAY-2025