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Prachand NEET (2024)

Isomerism
Revision Practice Sheet

Single Correct Type Questions (1 to 20) 6. Which of the following would exhibit cis-trans
1. 2-butyne and 1, 3-butadiene are: isomerism?
(1) Chain isomer (1) CH3CH2CH = CH2
(2) Position isomer (2) ClCH = CHCl
(3) Functional isomer (3) ClCH = CCl2
(4) Tautomers (4) CH2=CH–COOH

2. Which of the following compounds can exhibit 7. Which one of the following compounds does not show
enantiomerism? tautomerism?
(1) CH3CH2NO2
(1) 3-hydroxy propanoic acid
(2) 3-hydroxy butanoic acid CH 3
|
(3) 4-hydroxy butanoic acid (2) CH 3 − C − N = O
|
(4) None of these CH 3

3. The number of meso form of the given compound is: O

||
CH3 − CH − CH − CH − CH3 CH3 − NH − C − CH3
| | | (3)
OH OH OH O O
|| ||
(1) 2 (2) 3 (4) CH3 − C − CH − C − OC2 H5
(3) 4 (4) 8 |
CH3

4. Which of the following conformations of n-butane is

least stable? 8. Which of the following dienes is chiral?
(1) Gauche (2) Anti (1) CH3 – CH = C = CH2
(3) Eclipsed (4) Fully eclipsed (2) CH3 – CH = CH – CH = CH2
(3) CH3 – CH = C = CH – CH3
5. Which one of the following statements regarding the (4) CH2 = CH – CH2 – CH = CH2
projection shown below is correct?
9. Which of the following pairs of compounds is a ring-
chain isomer?
CH3 − CH − CH − CH3
(1) | | and
OH OH

(1) Both the projections represent the same

(2) and
configuration
(2) Both (I) and (II) are optically active (3) CH2 = CH – CH2 – OH and
(3) Only (I) is optically active
(4) Only (II) is optically active
(4) and
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10. Among the following compounds, the one which will 14. C8H16 that can form cis-trans isomerism and also chiral
not show keto-enol tautomerism is: center is

(1) (2)
(1) (2)
(3) Both of these (4) None of these

15. Following eclipsed form of propane is repeated after

rotation of:
(3) (4)

11. Geometrical isomers are possible for:

(1) CH3 − CH2 − C − CH2CH3 (1) 60°
||
NOH (2) 120°
(3) 180°
(2) CH3CH2 − C − CH3
|| (4) 360°
O

(3) CH3CH2 − C − CH3 16. Which of the following exists as trans alkene?
||
NOH (1) Cyclopentene (2) Cyclohexene
(3) Cycloheptene (4) Cyclooctene
(4) C6 H5 − C − C6 H5
||
O 17. Which of the following is true regarding the
enantiomers?
12. The number of alkynes possible with molecular (1) They always exist as discrete pairs?
formula C5H8 is: (2) They are stable and isolable compounds.
(1) 2 (2) 3 (3) An equimolar mixture of enantiomers is called
(3) 4 (4) 5 racemic mixture.
(4) All are true.
13. Which of the following is not a metamer of compound
B is: 18. Which one of the following is optically inactive?
B: (1) Trans-1,2-dibromocyclopropane
(2) Trans-1-bromo-2-chlorocyclopropane
(3) Cis-1-bromo-2-chlorocyclopropane
(1) (4) Cis-1,2-dibromocyclopropane

19. What is true about cis-1,2-dimethylcyclopentane?

(2) (1) It is chiral
(2) It is achiral due to centre of symmetry
(3) It is achiral due to plane of symmetry
(3) (4) It is chiral due to centre of symmetry.

(4)
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20. The relation between the following two compounds is 24. Assertion-Metamers can also be chain or position
isomers.
Reason-The term tautomerism was introduced to
explain the reactivity of a substance according to two
possible structures.
(1) Both assertion and reason are correct and reason
(1) Position isomers is a correct explanation for assertion
(2) Functional isomers (2) Both assertion and reason are correct and reason
(3) Tautomer is not a correct explanation for assertion
(4) Metamer (3) Assertion is correct, Reason is incorrect
(4) Both assertion and reason are incorrect
Assertion and Reason Type Questions (21 to 25)
25. Assertion-All oximes show geometrical isomerism.
21. Assertion- All the carbon atoms in alkenes are sp3 Reason-Geometrical isomerism can be shown by
hybridized. ethene.
Reason- All the carbon atoms in alkanes are sp2 (1) Both assertion and reason are correct and reason
hybridized. is a correct explanation for assertion
(2) Both assertion and reason are correct and reason
(1) Both assertion and reason are correct and reason is not a correct explanation for assertion
is a correct explanation for assertion (3) Assertion is correct, Reason is incorrect
(2) Both assertion and reason are correct and reason (4) Both assertion and reason are incorrect
is not a correct explanation for assertion
Match the Column Type Questions (26 to 30)
(3) Assertion is correct, Reason is incorrect
26. Match the column
(4) Both assertion and reason are incorrect Column-I Column-II
(Molecule Name) (Structure)
(A) (Z) Penta-1, 3-diene (P)
22. Assertion- C6H14 and C5H12 both can show chain (B) (2E, 4E) Hexa – 2, 4- (Q)
isomerism. diene
Reason- C6H14 and C5H12 both form 3 chain isomers (C) (E)–1–Bromo–1– (R)
each, respectively. chloro–2–iodopropene
(1) Both assertion and reason are correct and reason
(D) (2E, 4E)–3 (S)
is a correct explanation for assertion Ethylhexa– 2, 4–diene
(2) Both assertion and reason are correct and reason
is not a correct explanation for assertion A B C D
(1) P S R Q
(3) Assertion is correct, Reason is incorrect (2) P S Q R
(4) Both assertion and reason are incorrect (3) P Q R S
(4) S R P Q
23. Assertion-Cis–1, 3-dihydroxy cyclohexane exists in
boat conformation.
Reason- In the chair form, there will not be hydrogen
bonding between the two hydroxyl groups.
(1) Both assertion and reason are correct and reason
is a correct explanation for assertion
(2) Both assertion and reason are correct and reason
is not a correct explanation for assertion
(3) Assertion is correct, Reason is incorrect
(4) Both assertion and reason are incorrect
27. Match the column
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Column-I Column-II 29. Match the column (Based on the possible number of
(Pair of molecule) (Type of isomerism geometrical isomers)
exhibited) Column-I Column-II
(A) 1, 2–dibromoethane and (P) Functional (A) CH3 – CH = CH – CH (P) 2
1, 1–dibromoethane isomerism = N – OH
(B) (Q) Position (B) (Q) 4
isomerism
and

(C) CH3–CH=CH– (R) 6

CH=CH–CH=CH–
CH3
(D) CH3–CH=CH– (S) 8
CH=CH–CH=CH–Ph
(C) n-Butane and isobutane (R) Geometrical A B C D
isomerism (1) Q P R S
(D) Acetic acid and methyl (S) Chain (2) Q P S R
formate isomerism (3) P Q R S
A B C D (4) P R S Q
(1) Q R P S
30. Match the column
(2) Q R S P
Column-I Column-II
(3) P Q R S
(Molecules) (Characteristics)
(4) P R Q S (A) (P) E

28. Match the column (More than one item in column–I

(B) (Q) Z
may be linked to the same item in column - II)
Column-I Column-II
(Molecule) (Number of chiral (C) OH (R) R-Configuration
|
centre)
HOOC − C − H
(A) (P) 0 |
CH3
(B) (Q) 1 (D) COOH (S) S-configuration
|
H2 N − C − H
|
CH3
(C) (R) 2
A B C D
(1) P Q S R
(2) P Q R S
(D) (S) 3 (3) Q P S R
(4) Q P R S
A B C D
(1) Q R P S
(2) Q R Q P
(3) P Q R S
(4) P Q S R
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Answer Key
1. (3) 16. (4)
2. (2) 17. (4)
3. (1) 18. (4)
4. (4) 19. (3)
5. (4) 20. (3)
6. (2) 21. (4)
7. (2) 22. (2)
8. (3) 23. (4)
9. (3) 24. (2)
10. (2) 25. (4)
11. (3) 26. (2)
12. (2) 27. (2)
13. (3) 28. (2)
14. (1) 29. (1)
15. (2) 30. (2)
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Hints and Solutions

1. (3)
Functional isomerism is shown by but-1-yne and but-
1,3-diene.
Alkynes having four or more carbon atoms are
functional isomers of dienes i.e., compounds
containing two double bonds.
7. (2)
2. (2) Compounds (1) shows nitro-aci nitro tautomerism.
The C3 of 3-hydroxy butanoic acid is chiral and hence Compound (2) does not show it. Compound (3) shows
optically active. amide-imidic acid tautomerism. Compound (4)
shows keto-enol tautomerism.
3. (1)
The molecules has plane of symmetry and contains 8 (3)
odd number of chiral centre. To calculate the number Disubstituted (at two different sp2) allenes are chiral
of meso compounds, the formula is due to lack of symmetry elements.
( n−1)
Number of meso forms = m = 2 2 9. (3)
Compounds with the same molecular formula but two
4. (4) different structures as cyclic and open-chain are
Fully eclipsed conformation is the least stable. called ring chain isomers of each other

5. (4) 10. (2)

Compound is optically inactive due to plane of  – H is present on bridge head so does not participate
symmetry. in tautomerism.

6 (2) 11. (3)

Geometrical isomerism: Doubly bonded carbon In oximes, the two different group around sp2 carbon
atoms have to satisfy the remaining two valences by makes the oxime geometrically active
joining with two atoms or groups. If the two atoms or stereoisomerism.
groups attached to each carbon atom are different,
they can be represented by YX C = C XY like 12. (2)
structure. YX C = C XY can be represented in space There are 3 alkynes possible for the Molecular
in the following two ways: formula C5H8
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21. (4)
In alkanes, there are 3 sigma bonds hence, the
possible hybridization is sp2.
In alkanes, there are 4 sigma bonds hence, the
possible hybridization is sp3.
13. (3)
22. (2)
Metamers are the isomers having the same molecular
Chain isomerism can be defined as having same
formula but different alkyl groups on two sides of
molecular formula but the different chain.
functions groups.
Thus alkanes having more than 3 carbon atoms
14. (1) exhibit chain isomerism.
Compound (1) has two different group at both sp2 Both alkanes will have types of chain length.
centre and has one asymmetric carbon.
23. (4)
15. (2) Cis 1, 3 dihydroxy cyclohexane
The given conformer is fully eclipsed. The same
conformer can be obtained by rotating one of the C-
atom by 120º.

16. (4)
Cycloalkenes of seven or less carbons in the ring
Cis 1, 3 dihydroxy cyclohexane exist in chair
exists only as cis-alkene due to ring strain.
conformation because in chair conformation, there
will be Hydrogen bonding between two hydroxyl
17. (4)
group.
All the above statements reflect the properties of
enantiomers.
24. (2)
Metamerism is a type of isomerism in which the
18. (4) compounds have the same molecular formula but they
Cis-1,2-dibromocyclopropane has plane of symmetry differ in the alkyl groups around the functional group.
and its mirror-image is superimposable on it. This type of isomerism is observed in ethers,
thioethers, esters, secondary amines and ketones.
19. (3) Metamers can also show chain or position isomerism.
It contains a plane of symmetry making is achiral. Since, if the functional group is a part of the chain
then the carbon skeleton can differ on either side of
the functional group.
20. (3)
Tautomerism was introduced by C.P Laar to explain
These are constitutional isomers. The transfer of H+ the chemical reactivity of a substance according to
generates as new functional group. These have two possible structures.
amide-imidic acid tautomerism.
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25. (4) 29. (1)

Oximes having the following general structure show One C=C having different substituents at carbon
geometrical isomerism. generates two geometrical isomers.

30. (2)
If the highest priority groups are on the opposite side
Ethene does not show geometrical isomers in the of C=C, assign (E) otherwise (Z). At a chiral carbon,
each sp2 carbon has same type of atoms. if four different groups are placed in such manner that
on moving from 1 → 2 → 3 is clockwise, assign R
26. (2) otherwise S, keeping the lowest priority group below
Select the longest chain of hydrocarbon. Assign (E) the plane of the paper
and (Z) according to the priority of the groups around
C=C.

27. (2)
Draw the structure of each compound and the name
the type of constitutional isomerism or
configurational isomerism exhibited by them.

28. (2)
Check the carbon or C=C at which 4 different
substituents are placed.

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