Isomerism (Workbook + Practice Problems) - 1
Isomerism (Workbook + Practice Problems) - 1
Ummeed NEET 2025 C.Q 2. Which of the following pairs of compounds are
positional isomers? (JEE Mains 2015)
C.Q. 3. The compound which shows metamerism is:
(NEET 2021)
(1)
(1) C3H8O (2) C3H6O
ISOMERISM Workbook
(3) C4H10O (4) C5H12
General Introduction: 1. Chain Isomerism (2) Solution.
1. Isomers have the same molecular formula but different Definition: Compounds which have the same
physical and chemical properties. molecular formula but have different parent chain.
2. Compounds having same molecular formula, but
different connectivity, different bonding pattern (3)
(structural isomerism) or different 3-D relative
arrangement (stereoisomerism) is known as isomers.
3. This phenomenon is known as isomerism.
4. Isomers are those which can be separated at room (4)
temperature. 4. Functional Isomerism
5. Isomers always have same Degree of Unsaturation Definition: Compounds which have same molecular
(DU). formula but have different functional groups.
Solution.
C.Q. 1. Which of the following pairs of compounds are chain
isomers?
(1) n-Butyl alcohol and s-butyl alcohol
(2) isobutyl alcohol and t-butyl alcohol
(3) s-butyl alcohol and t-butyl alcohol
(4) n-propyl alcohol and isopropyl alcohol
Solution. 3. Metamerism
2. Position Isomerism
Types of Structural Isomerism Definition: Compounds which have the same (A) (B) B. Aldehydes and Ketones
1. Chain Isomerism molecular formula but have different position of branch
2. Position Isomerism or F.G (double or triple bond).
3. Metamerism (C) (D)
4. Functional Isomerism C. Cyanides and isocyanides
5. Tautomerism
6. Ring-Chain Isomerism
(E) (F)
3 4
E. Acids and esters (1) (A)-(II), (B)-(I), (C)-(IV), (D)-(III) Q. Tautomerism Exhibits or not? C.Q. 7 Which among the given molecules can exhibit
(2) (A)-(III), (B)-(I), (C)-(II), (D)-(IV) tautomerism? (NEET 2016)
(3) (A)-(I), (B)-(III), (C)-(IV), (D)-(II)
(A) CH3 − C− H (B)
(4) (A)-(III), (B)-(I), (C)-(IV), (D)-(II) ||
Solution. O
Solution.
F. Diene and yne (1) III only
(2) Both I and III
(3) Both I and II
(4) Both II and III
Solution.
C.Q. 4. Given below are two statements: C.Q. 6. In which of the following, functional group isomerism
is not possible? (NCERT Exemplar)
Statement (I): and are isomeric (1) Alcohols Q. Tautomerism Exhibits or not?
compounds. (2) Aldehydes
Statement (II): are (3) Alkyl halides
(4) Cyanides
functional group isomers. Solution. (A) (B)
In the light of the above statements, choose the correct
answer from the options given below:
6. Ring-Chain Isomerism
(JEE Mains 2025) Solution.
Definition: Compounds which have the same
(1) Statement I is true, but Statement II is false.
molecular formula but one compound is chain & the
(2) Both Statement I and Statement II are true.
(3) Statement I is false, but Statement II is true. other is cyclic.
(4) Both Statement I and Statement II are false
Solution.
5. Tautomerism
Definition: Intramolecular proton (H+) transfer.
Bredt’s Rule:
Calculation of No. of Structural Isomers: C.Q. 9 The number of different chain isomers for C7H16 is Stereo Isomerism: Geometrical Isomerism
__________. (JEE Mains 2024) Definition: The compounds that have the same 1. Arises due to Restricted rotation around
Solution. constitution and sequence of covalent bonds but differ C=C, C=N, N=N, Cycloalkanes etc.
in relative positions of their atoms or groups in space are G.I. are not interconvertible at room temperature
called stereoisomers. because of π-bond dissociation energy (62 Kcal).
7 8
Condition for exhibition of Geometrical Isomerism Types of G.I. Rule 02: If the atomic number of first atom is same, C.Q. 14. Which one of the following will show geometrical
Restricted sites must have different groups. 1. Cis-Trans then go for the next atom and apply the rule number 01. isomerism? (JEE Mains 2024)
2. E/Z isomers
Case 01: Cis-Trans System
C=C
If similar groups are on the same side, then cis otherwise (1) (2)
trans.
(3) (4)
(a) (b)
Rule 04: In the case of multiple bonds and Rings. (1) Methyl-2-methylhepta (2E, 5E) dienoate
(c) (d) (2) Methyl-2-methylhepta (2Z, 5Z) dienoate
(3) Methyl-2-methylhepta (2E, 5Z) dienoate
(4) Methyl-2-methylhepta (2Z, 5E) dienoate
(e) Solution.
Case 02: Z-E System
C.I.P. Rules
Solution. Rule 01: Greater the atomic number, higher will be the
priority.
9 10
Case 03: Cycloalkanes Case 2. If End groups are same. (Symmetrical) (C) C6H5–CH = CH–CH = CH–CH = CH–C6H5 Properties of Cis-Trans
Minimum 2 sp3 carbon must be attached at different site Solution. 1. Dipole moment
to show G.I in cycloalkanes.
2. Boiling Point
5. Stability
6. Solubility
Q. Calculate the number of geometrical isomers for the
following compounds.
(A) C6H5–CH = CH–CH = CH–CH = CH–CH = CH–Cl
Calculation of No. of G.I.
Solution.
Case 1. If End groups are different. (Unsymmetrical) C.Q. 18. The incorrect statements regarding geometrical
C.Q. 17. Predict the number of geometrical isomers for 2, 4- isomerism are: (JEE Mains 2025)
dimethylpent-2-ene.
(A) Propene shows geometrical isomerism.
(1) 0 (2) 2
(B) Trans isomer has identical atoms/groups on the
(3) 4 (4) 6
opposite sides of the double bond.
Solution. (C) Cis-but-2-ene has higher dipole moment than
trans-but-2-ene.
(D) 2-methylbut-2-ene shows two geometrical
(B) Cl–CH = CH–CH = CH–CH = CH–CH = CH–Cl isomers.
(E) Trans-isomer has lower melting point than cis
Solution.
isomer.
Choose the correct answer from the options given
below:
(1) (A) and (E) Only
(2) (B) and (C) Only
(3) (C), (D) and (E) Only
(4) (A), (D) and (E) Only
11 12
Solution. C.Q. 21. Which of the following is correct set of physical C.Q. 22. Total number of compounds with Chiral carbon Optical & Specific Rotation:
properties of geometrical isomers? atoms from following is ________. (JEE Mains 2024)
C.Q. 20. The incorrect statement regarding the geometrical Basic Term:
Chiral Carbon: sp3 tetrahedral carbon atom attached C.Q. 23. If a solution of a compound (30g/100mL of solution)
isomers of 2-butene is: (JEE Mains 2024)
with four different groups. has measured rotation of +15° in a 2 dm long sample
(1) cis-2-butene and trans-2-butene are not tube. The specific rotation of this compound is:
interconvertible at room temperature. (1) +50o (2) +25o
(2) cis-2-butene has less dipole moment than trans- (3) +15o (4) +7.5o
2-butene. Solution.
(3) trans-2-butene is more stable than cis-2-butene.
(4) cis-2-butene and trans-2-butene are
stereoisomers.
Solution.
13 14
POS (Plane of Symmetry): COS (Center of Symmetry): (ii) If molecules are cyclic with odd ring. C.Q. 25. Which of the following acids do not exhibit optical
An Imaginary plane which can divide a molecule into An Imaginary point from which opposite lines are isomerism? (AIPMT 2012)
two equal parts. drawn the same group will meet. (1) Lactic acid (2) Tartaric acid
(3) Maleic acid (4) 𝛼-amino acids
Solution.
(3)
Conditions for Optical Activity of Compounds C.Q. 27. Which of the following compounds exhibit
stereoisomerism? (AIPMT 2002)
B. If more than one chiral carbons are present.
(4) (1) 2-methylbutene-1
(i) If molecules are acyclic. (2) 3-methylbutyne-l
(3) 3-methylbutanoic acid
Solution. (4) 2-methylbutanoic acid
Solution.
15 16
R/S Configuration: C.Q. 30. The structure of (S)-2-fluorobutane is best Relation b/w compounds when only two or more chiral
Case 01: In Fischer Projection Formula C.Q. 29. The absolute configuration of represented by: carbons are present:
Answer: Enantiomers or Identical or Diastereomers
(1) Diastereomers: Non superimposable & not mirror
is:
(JEE Mains 2016) image.
(1) (2R, 3S) (2) (2S, 3R)
(3) (2S, 3S) (4) (2R, 3R)
Solution. (2)
(3)
(4)
Meso Compounds: C.Q. 33. Among the following which one can have meso C.Q. 34. The separation of a racemic mixture into pure D/L Configuration:
1. Optical isomers have more than one with form? enantiomers is termed as: 1. Highest priority group should be on top position.
POS/COS. (1) CH3CH(OH)CH(Cl)C2H5 (1) Racemization 2. Carbon should lie on vertical line.
2. Meso compounds are optically inactive due to (2) CH3CH(OH)CH(OH)CH3 (2) Isomerization 3. Check the last chiral carbon.
internal compensation. (3) C2H5CH(OH)CH(OH)CH3 If OH/NH2 right then “D”
(3) Resolution
3. Mirror image of meso compounds represent its If OH/NH2 left then “L”
(4) HOCH2CH(Cl)CH3 (4) Equilibration
identical molecule. Solution. Solution.
4. Meso compounds cannot have enantiomers.
Resolution:
Separation of Enantiomers from RM is called
resolution.
Racemic Mixture:
1. Equimolar mixture of two enantiomers.
2. RM is optically inactive due to external
compensation.
3. Each enantiomer is optically active.
19 20
Erythro/Threo: Epimer & Anomers: Case 3. If molecules are symmetrical. (n = odd) Calculation of Stereoisomers:
Case 1. If molecules are unsymmetrical.
(1) L-erythrose, L-threose, L-erythrose, D-threose C.Q. 37. Number of optical isomers possible for 2- C.Q. 38. How many different stereoisomers are possible for
(2) D-threose, D-erythrose, L-threose, L-erythrose chlorobutane __________. (JEE Mains 2024) the given molecule? (JEE Mains 2025)
(3) L-erythrose, L-threose, D-erythrose, D-threose Solution. CH3 − CH − CH = CH − CH3
(4) D-erythrose, D-threose, L-erythrose, L-threose |
Solution. OH
(1) 3 (2) 2
(3) 1 (4) 4
Solution.
21 22
C.Q. 39. The possible number of stereoisomers for 5-phenyl Conformational Isomerism: C.Q. 41. With respect to the conformers of ethane, which of Torsional strain: The strain arises due to repulsion between
pent-4-en-2-ol is __________ . (JEE Mains 2025) the following statements is true? (NEET 2017) bond pair electrons.
Solution.
(1) Bond angle changes but bond length remains
same.
(2) Both bond angle and bond length change.
(3) Both bond angles and bond length remain same.
(4) Bond angle remains same but bond length
changes.
Solution.
NEET
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Practice Problems
Conformation Isomerism in Butane: Conformation Isomerism in Cyclohexane
Some Basic principles and Techniques (Isomerism)
Q1 The number of isomeric structures possible for a Q7 Match List-I with List-II.
molecule having molecular formula C5H12, is: List-I List-II
(A) 2 (B) 3 Chain
(A) (I)
(C) 4 (D) 5 Isomers
Q2 Position
(B) (II) isomers
C.Q. 43. Which of the following conformations of butane has (A) 2-butene (B) 2-butyne
C.Q. 44. Most stable form of cyclohexane is:
the lowest energy? (C) 2-butanol (D) butanal
(1) Boat (2) Chair
(1) Anti (2) Gauche
(3) Skew (4) Eclipsed Q6 Total number of stereoisomers of compound is:
(3) Staggered (4) Eclipsed
(A) I and II (B) I and III
(C) 4 (D) 3
सपने वो नह ीं, जो आप सोते वक़्त दे खते हैं, सपने वो होते हैं, जो आपको सोने नह ीं दे ते! Q9 Given below are two statements: One is labelled
as Assertion (A) and the other is labelled as
Reason (R): Which of the following conformers for ethylene (B) Assertion (A) is false and Reason (R) is true.
Assertion (A): glycol is most stable: (C) Both Assertion (A) and Reason (R) are true
(A) and Reason (R) is a correct explanation of
Assertion (A).
(D) Both Assertion (A) and Reason (R) are true
but Reason (R) is not a correct explanation of
Compound-I and II are enantiomers. Assertion (A).
Reason (R): Non superimposable mirror images (A) I, II, III (B) I, III, IV
(B) Q16 Given below are two statements: one is labelled
are enantiomers. (C) II, III (D) II, III, IV
as Assertion A and the other is labelled as
In the light of the above statements, choose the
Reason R: Q21 A position isomer of pentan-2-one is:
correct answer from the options given below:
Assertion A: Alkanes having more than three (A) Pentan-3-one
(A) Assertion (A) is true and Reason (R) is false.
carbon atoms exhibit chain isomerism. (B) 3-Methylbutan-2-one
(B) Assertion (A) is false and Reason (R) is true.
Reason R: All carbon atoms in alkanes are sp (C) Pentan-1-al
(C) Both Assertion (A) and Reason (R) are true
hybridized. (D) 2,2-Dimethylpropanal
(C)
and Reason (R) is a correct explanation of
In the light of the above statements, choose the
Assertion (A). Q22 Which of the following pairs of compounds are
correct answer from the options given below.
(D) Both Assertion (A) and Reason (R) are true not functional isomers?
(A) Assertion (A) is true and Reason (R) is false.
but Reason (R) is not a correct explanation of (A)
(B) Assertion (A) is false and Reason (R) is true.
Assertion (A).
(C) Both Assertion (A) and Reason (R) are true
Q10 Identify E and Z configuration in the following (D) and Reason (R) is a correct explanation of
(B)
compounds; Assertion (A).
(D) Both Assertion (A) and Reason (R) are true
but Reason (R) is not a correct explanation of
(C)
Assertion (A).
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(D) Both Statement I and Statement II are B. CH3CH2CI and CH3CH2Br (A) chain isomers
incorrect. C. CH3CH2COCl and ClCH2CH2CHO (B) metamers
The correct option is: (C) identical
Q24
(A) A only (B) A and B only (D) position isomers
(C) A and C only (D) B and C only
Q33 How many structural isomer of C5H11OH will be
(A) Position isomers Q28 The number of isomers possible with molecular primary alcohols: (D)
(B) Functional isomers formula C2 H4 Cl2 is : (A) 2 (B) 3
(C) Identical (A) 2 (B) 3 (C) 4 (D) 5
(D) Chain isomers (C) 4 (D) 6
Q34 The functional isomer of ethers is:
Q25 m-Dichlorobenzene and p-Dichlorobenzene are: Q29 The number of ether metamers represented by (A) Aldehyde (B) Ketones
(A) ring-chain isomers Q39 Geometrical isomerism is due to:
the molecular formula C4H10O is; (C) Alcohols (D) Esters
(B) functional isomers (A) The restricted rotation about a double bond
(A) 1 (B) 2
(C) position isomers Q35 Keto-enol tautomerism observed in- (B) The presence of keto group
(C) 3 (D) 4
(D) tautomers (A) (C) The presence of CH(OH) group
Q30 The two optical isomers given below are namely? (D) The presence of an asymmetric carbon
Q26 Which of the following has ‘S’ configuration? (B)
(A) Q40 Which of the following compounds is isomeric
with 2, 2, 4 , 4- Tetramethylhexane?
(C)
(A) 3-Ethyl -2, 2 -dimethylpentane
(B) 4-Isopropylheptane
(D)
(C) 4-Ethyl-3-methyl-4-n-propyloctane
(A) Enantiomers (D) 4,4-Diethyl-3-methylheptane
(B) Q36 How many position isomers are possible for
(B) Diastereomers
chlorophenol? Q41 Match List-I with List-II.
(C) Position isomers
(A) 2 (B) 3
(D) Meso compound List-II
(C) 4 (D) 5 List-I
(Number of chiral
Q31 Given below are two statements: (Compounds)
Q37 The total number of isomers in C6H3Cl3 is: center)
Statement I: 1, 2-dichloroethane is optically
(C) (A) Two (B) Three
active.
(C) Four (D) Five (A) (I) 4
Statement II: Meso compound is optically active.
In the light of the above statements, choose the Q38 The compound which has maximum number of
most appropriate answer from the options given chiral centres is : (B) (II) 3
below; (A)
(D) (A) Statement-I is correct but Statement-II is
(C) (III) 1
incorrect.
(B) Statement-I is incorrect but Statement-II is
correct. (B) (D) (IV) 2
(C) Both Statement-I and Statement-II are
correct. Choose the correct answer from the options
(D) Both Statement-I and Statement-II are given below:
Q27 Which of the following pairs of structures
incorrect. (A) A-I, B-II, C-III, D-IV
represent isomers?
(C) (B) A-III, B-IV, C-II, D-I
Q32 CH3 − S − CH2 − CH3 and (C) A-I, B-I, C-IV, D-II
A. CH3 − CH2 − S − CH3 are: (D) A-IV, B-III, C-I, D-II
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