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Structural isomerism Questions in English

Class 11 Chemistry · 8-2.Organic Chemistry : Isomerism · Structural isomerism

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201
Medium
What is functional group isomerism? Explain with a suitable example.

Solution

When two or more compounds have the same molecular formula but possess different functional groups,they are called functional isomers,and this phenomenon is known as functional group isomerism.
Example: The molecular formula $C_3H_6O$ represents both an aldehyde and a ketone.
$1$. Propanal $(CH_3CH_2CHO)$: Contains an aldehyde functional group $(-CHO)$.
$2$. Propanone $(CH_3COCH_3)$: Contains a ketone functional group $(>C=O)$.
202
Medium
What is metamerism? Give an example.

Solution

(N/A) Metamerism is a type of structural isomerism that arises due to the presence of different alkyl chains on either side of the same functional group in a molecule.
Example: The molecular formula $C_4H_{10}O$ (ether) exhibits metamerism.
$(i)$ Methoxypropane: $CH_3-O-CH_2-CH_2-CH_3$
$(ii)$ Ethoxyethane: $CH_3-CH_2-O-CH_2-CH_3$
203
Medium
What is structural isomerism? Give two examples of chain isomerism in alkanes. Or,explain the isomerism of alkanes having more than three carbon atoms using two examples.

Solution

(N/A) Structural isomers: Compounds having the same molecular formula but different structural arrangements are known as structural isomers.
This phenomenon is known as structural isomerism.
Chain isomers: If two or more compounds have the same molecular formula but different carbon chain structures,such compounds are known as chain isomers,and this phenomenon is known as chain isomerism. Alkanes having more than three carbon atoms exhibit chain isomerism.
Example-$1$: Butane $(C_4H_{10})$ has $2$ structural isomers:
$(i)$ $n$-butane: $CH_3-CH_2-CH_2-CH_3$ (continuous chain).
$(ii)$ $2$-methylpropane (isobutane): $CH_3-CH(CH_3)-CH_3$ (branched chain).
Example-$2$: Pentane $(C_5H_{12})$ has $3$ isomers:
$(i)$ $n$-pentane: $CH_3-CH_2-CH_2-CH_2-CH_3$ (straight chain).
$(ii)$ Isopentane ($2$-methylbutane): $CH_3-CH(CH_3)-CH_2-CH_3$ (branched chain).
$(iii)$ Neopentane ($2,2$-dimethylpropane): $CH_3-C(CH_3)_2-CH_3$ (branched chain).
204
Medium
Give the number of structural isomers for methane,ethane,propane,butane,pentane,hexane,heptane,and decane.

Solution

(N/A) Methane $(CH_{4})$,ethane $(C_{2}H_{6})$,and propane $(C_{3}H_{8})$ do not exhibit structural isomerism as they have only one possible structure.
Name of Hydrocarbon Number of Isomers
Butane $(C_{4}H_{10})$ $2$
Pentane $(C_{5}H_{12})$ $3$
Hexane $(C_{6}H_{14})$ $5$
Heptane $(C_{7}H_{16})$ $9$
Decane $(C_{10}H_{22})$ $75$
205
Medium
Write the types of isomers for $C_4H_6$ (alkyne) and provide one example for each.

Solution

(N/A) The molecular formula $C_4H_6$ corresponds to an alkyne (general formula $C_nH_{2n-2}$).
$(a)$ Position Isomers:
$CH_3-CH_2-C \equiv CH$ (But$-1-$yne)
$CH_3-C \equiv C-CH_3$ (But$-2-$yne)
$(b)$ Chain Isomers:
There are no chain isomers for $C_4H_6$ alkynes as the carbon chain cannot be branched without violating valency.
$(c)$ Functional Isomers (Dienes):
$CH_2=C=CH-CH_3$ (Buta$-1,2-$diene)
$CH_2=CH-CH=CH_2$ (Buta$-1,3-$diene)
$(d)$ Cyclic Isomers:
$1$-Methylcyclopropene,$3$-Methylcyclopropene,and Cyclobutene.
206
Advanced
Provide the structures and names of the chain isomers of the molecular formula $C_6H_{14}$ that contain only a methyl group as a substituent.

Solution

(N/A) The molecular formula $C_6H_{14}$ corresponds to hexane. The chain isomers that contain only a methyl group as a substituent are as follows:
StructureName
$(i) \ CH_3-CH(CH_3)-CH_2-CH_2-CH_3$$2\text{-methylpentane}$
$(ii) \ CH_3-CH_2-CH(CH_3)-CH_2-CH_3$$3\text{-methylpentane}$
207
Difficult
Provide the structures of chain isomers of $C_6H_{14}$ that contain two methyl groups,along with their $IUPAC$ names.

Solution

(N/A) The molecular formula $C_6H_{14}$ corresponds to an alkane. Chain isomers with two methyl groups are:
$(i)$ $CH_3-C(CH_3)_2-CH_2-CH_3$: The longest chain has $4$ carbon atoms,and there are two methyl groups at the $2^{nd}$ position. Its $IUPAC$ name is $2,2-Dimethylbutane$.
(ii) $CH_3-CH(CH_3)-CH(CH_3)-CH_3$: The longest chain has $4$ carbon atoms,and there are methyl groups at the $2^{nd}$ and $3^{rd}$ positions. Its $IUPAC$ name is $2,3-Dimethylbutane$.
208
Medium
What is isomerism? Explain with a suitable example.

Solution

(N/A) Isomerism is the phenomenon in which two or more compounds have the same molecular formula but different structural arrangements of atoms.
For example,$n$-butane $(CH_3-CH_2-CH_2-CH_3)$ undergoes isomerization in the presence of anhydrous $AlCl_3$ and $HCl$ gas to form isobutane $(CH_3-CH(CH_3)-CH_3)$.
This occurs because the branched-chain isomer is thermodynamically more stable than the straight-chain isomer.
209
Medium
Explain the following terms:
$(a)$ Isomerism
$(b)$ Position isomerism
$(c)$ Chain isomerism
$(d)$ Functional group isomerism
$(e)$ Metamerism
$(f)$ Optical isomerism

Solution

(N/A) Isomerism: Compounds having the same molecular formula but different physical or chemical properties due to different arrangements of atoms are called isomers,and the phenomenon is called isomerism.
$(b)$ Position isomerism: It occurs when the position of a functional group or substituent changes along the same carbon chain (e.g.,$CH_3-CH_2-CH_2-OH$ and $CH_3-CH(OH)-CH_3$).
$(c)$ Chain isomerism: It arises due to the difference in the arrangement of the carbon skeleton (e.g.,$n$-butane and isobutane).
$(d)$ Functional group isomerism: It occurs when compounds have the same molecular formula but contain different functional groups (e.g.,ethanol $CH_3CH_2OH$ and dimethyl ether $CH_3OCH_3$).
$(e)$ Metamerism: It arises due to the different distribution of carbon atoms on either side of a polyvalent functional group (e.g.,diethyl ether $CH_3CH_2-O-CH_2CH_3$ and methyl propyl ether $CH_3-O-CH_2CH_2CH_3$).
$(f)$ Optical isomerism: It is a type of stereoisomerism where isomers are non-superimposable mirror images of each other,known as enantiomers,which rotate plane-polarized light.
210
Medium
Identify the pairs of compounds which are functional group isomers.
$I$. $CH_3-CH_2-CH_2-CH_2-OH$
$II$. $CH_3-CH_2-CH(OH)-CH_3$
$III$. $(CH_3)_3C-OH$
$IV$. $CH_3-CH(CH_3)-CH_2-OH$
$V$. $CH_3-CH_2-O-CH_2-CH_3$
$VI$. $CH_3-O-CH_2-CH_2-CH_3$
$VII$. $CH_3-O-CH(CH_3)_2$

Solution

(A) Functional group isomers are compounds that have the same molecular formula but different functional groups.
$I, II, III, IV$ are alcohols (functional group $-OH$).
$V, VI, VII$ are ethers (functional group $-O-$).
Any pair consisting of one alcohol and one ether will be functional group isomers (e.g.,$I$ and $V$).
$V, VI, VII$ are ethers and exhibit metamery due to different alkyl groups attached to the oxygen atom.
211
MediumMCQ
Identify the pairs of compounds that represent position isomerism:
$(I)$ $CH_3-CH_2-CH_2-CH_2-OH$
$(II)$ $CH_3-CH_2-CH(OH)-CH_3$
$(III)$ $CH_3-C(CH_3)(OH)-CH_3$
$(IV)$ $CH_3-CH(CH_3)-CH_2-OH$
$(V)$ $CH_3-CH_2-O-CH_2-CH_3$
$(VI)$ $CH_3-O-CH_2-CH_2-CH_3$
$(VII)$ $CH_3-O-CH(CH_3)-CH_3$
A
$(I), (II)$ and $(III), (IV)$
B
$(VI), (VII)$
C
$(I), (II)$ and $(VI), (VII)$
D
$(I), (II)$; $(III), (IV)$ and $(VI), (VII)$

Solution

(D) Position isomers have the same molecular formula and same carbon skeleton but differ in the position of the functional group or substituent on the carbon chain.
- Pair $(I)$ and $(II)$ are position isomers ($Butan-1-ol$ and $Butan-2-ol$).
- Pair $(III)$ and $(IV)$ are position isomers ($2-Methylpropan-2-ol$ and $2-Methylpropan-1-ol$).
- Pair $(VI)$ and $(VII)$ are position isomers ($1-Methoxypropane$ and $2-Methoxypropane$).
212
MediumMCQ
Identify the pairs of compounds that represent position isomerism.
$(I)$ $CH_3-CH_2-CH_2-CH_2-OH$
$(II)$ $CH_3-CH_2-CH(OH)-CH_3$
$(III)$ $CH_3-C(OH)(CH_3)-CH_3$
$(IV)$ $CH_3-CH(CH_3)-CH_2-OH$
$(V)$ $CH_3-CH_2-O-CH_2-CH_3$
$(VI)$ $CH_3-O-CH_2-CH_2-CH_3$
$(VII)$ $CH_3-O-CH(CH_3)-CH_3$
A
$(I), (II)$ and $(VI), (VII)$
B
$(I), (II)$ and $(V), (VI)$
C
$(I), (III)$ and $(II), (IV)$
D
$(III), (IV)$ and $(V), (VII)$

Solution

(A) Position isomers have the same molecular formula and same functional group but differ in the position of the functional group on the parent chain.
- In $(I)$ $CH_3-CH_2-CH_2-CH_2-OH$ (butan$-1-$ol) and $(II)$ $CH_3-CH_2-CH(OH)-CH_3$ (butan$-2-$ol),the position of the $-OH$ group differs on the same butane chain.
- In $(VI)$ $CH_3-O-CH_2-CH_2-CH_3$ ($1$-methoxypropane) and $(VII)$ $CH_3-O-CH(CH_3)-CH_3$ ($2$-methoxypropane),the position of the $-OCH_3$ group differs on the same propane chain.
- Therefore,$(I), (II)$ and $(VI), (VII)$ are pairs of position isomers.
213
MediumMCQ
Identify the pairs of compounds that represent chain isomerism among the following:
$I. CH_3-CH_2-CH_2-CH_2-OH$ (Butan$-1-$ol)
$II. CH_3-CH_2-CH(OH)-CH_3$ (Butan$-2-$ol)
$III. (CH_3)_3C-OH$ ($2$-Methylpropan$-2-$ol)
$IV. (CH_3)_2CH-CH_2-OH$ ($2$-Methylpropan$-1-$ol)
A
$I$ and $II$
B
$I$ and $IV$
C
$II$ and $III$
D
$III$ and $IV$

Solution

(B) Chain isomerism occurs when compounds have the same molecular formula but different carbon chain structures (e.g.,straight chain vs. branched chain).
$1$. $I$ $(CH_3-CH_2-CH_2-CH_2-OH)$ is a straight-chain alcohol (butan$-1-$ol).
$2$. $IV$ $((CH_3)_2CH-CH_2-OH)$ is a branched-chain alcohol ($2$-methylpropan$-1-$ol).
Both $I$ and $IV$ have the same molecular formula $(C_4H_{10}O)$ but differ in the arrangement of the carbon chain. Therefore,they represent chain isomerism.
214
EasyMCQ
Compounds with the same molecular formula but differing in their structures are called structural isomers. What type of structural isomerism is shown by $CH_3-S-CH_2-CH_2-CH_3$ and $CH_3-S-CH(CH_3)_2$?
A
Chain isomerism
B
Position isomerism
C
Metamerism
D
Functional isomerism

Solution

(C) $Metamerism$ is a type of structural isomerism that occurs when different alkyl groups are attached to the same polyvalent functional group (such as $-O-$,$-S-$,$-NH-$,or $-CO-$).
In the given pair,the alkyl groups attached to the sulfur atom are different (methyl and $n$-propyl in the first,methyl and isopropyl in the second). Therefore,they are metamers.
Solution diagram
215
DifficultMCQ
Assertion $A$: Enol form of acetone $[CH_{3}COCH_{3}]$ exists in $< 0.1 \%$ quantity. However,the enol form of acetylacetone $[CH_{3}COCH_{2}COCH_{3}]$ exists in approximately $15 \%$ quantity.
Reason $R$: Enol form of acetylacetone is stabilized by intramolecular hydrogen bonding,which is not possible in the enol form of acetone. Choose the correct statement:
A
$A$ is false but $R$ is true
B
Both $A$ and $R$ are true and $R$ is the correct explanation of $A$
C
Both $A$ and $R$ are true but $R$ is not the correct explanation of $A$
D
$A$ is true but $R$ is false

Solution

(B) The keto-enol tautomerism in acetone $[CH_{3}COCH_{3}]$ results in a very small amount of enol form $(< 0.1 \%)$ because the enol form is less stable than the keto form.
In acetylacetone $[CH_{3}COCH_{2}COCH_{3}]$,the enol form is significantly more stable due to the formation of a six-membered ring stabilized by intramolecular hydrogen bonding.
Therefore,both the assertion $A$ and the reason $R$ are true,and $R$ provides the correct explanation for $A$.
216
MediumMCQ
The compound with the molecular formula $C_3H_6O$ can show:
A
Positional isomerism
B
Both positional isomerism and metamerism
C
Metamerism
D
Functional group isomerism

Solution

(D) The molecular formula $C_3H_6O$ represents compounds such as propanal $(CH_3CH_2CHO)$ and propanone $(CH_3COCH_3)$.
Since these compounds have the same molecular formula but different functional groups (aldehyde and ketone),they exhibit functional group isomerism.
217
MediumMCQ
The compound which shows metamerism is:
A
$C_5H_{12}$
B
$C_3H_8O$
C
$C_3H_6O$
D
$C_4H_{10}O$

Solution

(D) Metamerism is shown by compounds having a polyvalent functional group (like ether,thioether,or amine) where the alkyl groups attached to the functional group differ.
$C_4H_{10}O$ can represent diethyl ether $(CH_3CH_2-O-CH_2CH_3)$ and methyl propyl ether $(CH_3-O-CH_2CH_2CH_3)$.
Since the alkyl groups attached to the oxygen atom are different in these two isomers,they are metamers.
Therefore,the correct option is $D$.
218
DifficultMCQ
Which one of the following pairs of isomers is an example of metamerism?
A
$CH_3-CH_2-CH_2-CH_2-CH_3$ and $CH_3-C(CH_3)_2-CH_3$
B
$CH_3-CH_2-CO-CH_2-CH_3$ and $CH_3-CO-CH_2-CH_2-CH_3$
C
$CH_3-CH_2-CH_2-NH_2$ and $CH_3-CH(NH_2)-CH_3$
D
$CH_3-CH_2-OH$ and $CH_3-O-CH_3$

Solution

(B) Metamerism arises due to the difference in the nature of the alkyl groups attached to the same polyvalent functional group (like $-O-$,$-CO-$,$-NH-$,etc.).
In the pair $CH_3-CH_2-CO-CH_2-CH_3$ (pentan$-3-$one) and $CH_3-CO-CH_2-CH_2-CH_3$ (pentan$-2-$one),the ketone functional group $(-CO-)$ is attached to different alkyl groups (ethyl-ethyl vs methyl-propyl). Thus,they are metamers.
219
MediumMCQ
The compound that readily tautomerises is
A
$CH_3COCH_2CO_2C_2H_5$
B
$CH_3COCH_2CH_2CH_3$
C
$CH_3COCH_3$
D
$(CH_3)_3CCOC(CH_3)_3$

Solution

(A) Tautomerism requires the presence of an $\alpha$-hydrogen atom adjacent to a carbonyl group.
Compounds with an active methylene group $(-CH_2-)$ flanked by two electron-withdrawing carbonyl groups (like in $\beta$-keto esters) undergo tautomerization most readily due to the stabilization of the resulting enol form by resonance and intramolecular hydrogen bonding.
In $CH_3COCH_2CO_2C_2H_5$ (ethyl acetoacetate),the methylene group is between two carbonyl groups,making it highly acidic and prone to tautomerization.
Therefore,the correct option is $A$.
220
MediumMCQ
The following compounds are:
Question diagram
A
geometrical isomers
B
positional isomers
C
optical isomers
D
functional group isomers

Solution

(D) The first compound is $hex-1-yne$ (an alkyne).
The second compound is $hexa-1,3-diene$ (a conjugated diene).
Since they possess different functional groups (triple bond vs. two double bonds),they are classified as functional group isomers.
221
MediumMCQ
The following two compounds are:
Question diagram
A
geometrical isomers
B
positional isomers
C
functional group isomers
D
optical isomers

Solution

(B) The given compounds are $CH_3-CH=CH-CH_3$ (but-$2$-ene) and $CH_3-CH_2-CH=CH_2$ (but-$1$-ene).
Both compounds have the same molecular formula $C_4H_8$ but differ in the position of the double bond in the carbon chain.
Therefore,they are positional isomers.
222
MediumMCQ
The number of possible structural isomers of $C_3H_4$ is $...$
A
$1$
B
$2$
C
$3$
D
$4$

Solution

(B) . The molecular formula $C_3H_4$ corresponds to a degree of unsaturation of $2$. The possible structural isomers are:
$1$. Propyne: $CH_3-C\equiv CH$
$2$. Cyclopropene: $A$ three-membered ring with one double bond.
223
MediumMCQ
Among the four compounds,$(i)$ acetone,$(ii)$ propanol,$(iii)$ methyl acetate and $(iv)$ propionic acid,the two that are isomeric are
A
methyl acetate and acetone
B
methyl acetate and propanol
C
propionic acid and methyl acetate
D
propionic acid and acetone

Solution

(C) The molecular formulas for the given compounds are as follows:
acetone: $C_3H_6O$
propanol: $C_3H_8O$
methyl acetate: $C_3H_6O_2$
propionic acid: $C_3H_6O_2$
Since the molecular formulas for both propionic acid $(CH_3CH_2COOH)$ and methyl acetate $(CH_3COOCH_3)$ are the same $(C_3H_6O_2)$ but they possess different functional groups,they are functional isomers.
224
MediumMCQ
Which of the following is a metamer of the given compound $(X)$?
Question diagram
A
$N$-phenylbenzamide
B
$4-$formyl-$N$-cyclohexylaniline
C
$N$-cyclohexylcyclohexanecarboxamide
D
$N$-cyclohexylbenzamide

Solution

(D) Metamers are isomers that have the same molecular formula and the same functional group,but differ in the nature of the alkyl or aryl groups attached to either side of the functional group.
The given compound $(X)$ is $N$-phenylcyclohexanecarboxamide,which has a cyclohexyl group on one side of the amide functional group and a phenyl group on the other.
To form a metamer,we need to change the distribution of the carbon atoms attached to the amide nitrogen and carbonyl carbon while keeping the total number of carbon atoms and the functional group the same.
Compound $(D)$,$N$-cyclohexylbenzamide,is a metamer of $(X)$ because it has the same molecular formula and the same amide functional group,but the phenyl group is now attached to the carbonyl carbon and the cyclohexyl group is attached to the nitrogen atom.
225
AdvancedMCQ
The total number of cyclic isomers possible for a hydrocarbon with the molecular formula $C_4H_6$ is
A
$4$
B
$5$
C
$6$
D
$8$

Solution

(B) The molecular formula $C_4H_6$ corresponds to a degree of unsaturation (double bond equivalent) of $4 - (6/2) + 1 = 2$.
For cyclic isomers,we consider structures with one ring and one double bond,or two rings.
The possible cyclic isomers are:
$1$. Cyclobutene
$2$. $1-$Methylcyclopropene
$3$. $3-$Methylcyclopropene
$4$. Methylenecyclopropane
$5$. Bicyclobutane
Thus,there are a total of $5$ cyclic isomers.
226
MediumMCQ
Newman projections $P$,$Q$,$R$,and $S$ are shown below:
Which one of the following options represents identical molecules?
Question diagram
A
$P$ and $Q$
B
$Q$ and $S$
C
$Q$ and $R$
D
$R$ and $S$

Solution

(C) To determine if the molecules are identical,we assign $IUPAC$ names to each Newman projection:
$P$: The structure corresponds to $2,3,3$-trimethylpentan-$2$-ol.
$Q$: The structure corresponds to $3$-ethyl-$2$-methylpentan-$2$-ol.
$R$: The structure corresponds to $3$-ethyl-$2$-methylpentan-$2$-ol.
$S$: The structure corresponds to $3$-ethyl-$2$-methylpentan-$3$-ol.
Comparing the $IUPAC$ names,$Q$ and $R$ have the same name ($3$-ethyl-$2$-methylpentan-$2$-ol),which means they represent the same molecule. Thus,the correct option is $C$.
227
MediumMCQ
Given below are two statements :
Statement $(I) :$ $CH_3CH=CHCH_3$ and $cyclobutane$ are isomeric compounds.
Statement $(II) :$ $CH_3CH_2CH_2CH_2NH_2$ and $(CH_3CH_2)_2NH$ are functional group isomers.
In the light of the above statements,choose the correct answer from the options given below :
A
Both Statement $I$ and Statement $II$ are false
B
Both Statement $I$ and Statement $II$ are true
C
Statement $I$ is true but Statement $II$ is false
D
Statement $I$ is false but Statement $II$ is true

Solution

(B) Statement $-I \rightarrow$ True
$CH_3CH=CHCH_3$ and $cyclobutane$ both have the molecular formula $C_4H_8$. They are ring-chain isomers,which is a type of structural isomerism.
Statement $-II \rightarrow$ True
$CH_3CH_2CH_2CH_2NH_2$ ($1^{\circ}$ amine) and $(CH_3CH_2)_2NH$ ($2^{\circ}$ amine) have different functional groups (primary amine vs secondary amine). Therefore,they are functional group isomers.
228
MediumMCQ
Identify the correct statements from the following. Choose the correct answer from the options given below.
$A$. Pentan$-3-$one and Pentan$-2-$one are metamers.
$B$. Butanenitrile and Butaneisonitrile are functional isomers.
$C$. Butan$-1-$ol and Butan$-2-$ol are position isomers.
$D$. Butan$-1-$amine and $N$-methylpropan$-1-$amine are homologous.
A
$C \ \& \ D$ only
B
$B \ \& \ C$ only
C
$A \ \& \ B$ only
D
$A, B \ \& \ C$ only

Solution

(D) . Pentan$-3-$one $(CH_3CH_2COCH_2CH_3)$ and Pentan$-2-$one $(CH_3COCH_2CH_2CH_3)$ have different alkyl groups attached to the carbonyl group,so they are metamers. (Correct)
$B$. Butanenitrile $(CH_3CH_2CH_2CN)$ and Butaneisonitrile $(CH_3CH_2CH_2NC)$ have different functional groups (nitrile vs isonitrile),so they are functional isomers. (Correct)
$C$. Butan$-1-$ol $(CH_3CH_2CH_2CH_2OH)$ and Butan$-2-$ol $(CH_3CH_2CH(OH)CH_3)$ differ only in the position of the $-OH$ group,so they are position isomers. (Correct)
$D$. Butan$-1-$amine $(CH_3CH_2CH_2CH_2NH_2)$ is a primary amine,while $N$-methylpropan$-1-$amine $(CH_3CH_2CH_2NHCH_3)$ is a secondary amine. They are functional isomers,not homologs. (Incorrect)
Therefore,statements $A, B,$ and $C$ are correct.
229
MediumMCQ
Metamerism is shown by $:-$
A
Diethyl ether and $n$-propyl methyl ether
B
Ethyl alcohol and diethyl ether
C
Acetone and propionaldehyde
D
Propionic acid and acetic acid

Solution

(A) Metamerism arises due to the difference in the nature of the alkyl groups attached to the same polyvalent functional group (like $-O-$,$-S-$,$-NH-$,or $-CO-$).
In diethyl ether $(CH_3CH_2-O-CH_2CH_3)$,the oxygen atom is attached to two ethyl groups.
In $n$-propyl methyl ether $(CH_3CH_2CH_2-O-CH_3)$,the oxygen atom is attached to a methyl group and an $n$-propyl group.
Since the alkyl groups attached to the oxygen atom differ,these compounds exhibit metamerism.
230
MediumMCQ
Find out the incorrect relation in the following pair of compounds:
A
Option A
B
Option B
C
Option C
D
Option D

Solution

(C) Let's analyze each pair:
$(A)$ $CH_2=CH-OCH_3$ (methoxyethene) and oxetane $(C_3H_6O)$ are ring-chain isomers because one is an open-chain compound and the other is a cyclic compound with the same molecular formula.
$(B)$ $o$-methylbenzyl alcohol $(C_8H_{10}O)$ and $2,3$-dimethylphenol $(C_8H_{10}O)$ are functional isomers because they contain different functional groups (alcohol vs. phenol).
$(C)$ Butan-$2$-ol and butan-$1$-ol are position isomers because the position of the $-OH$ group changes,not the carbon chain length. Therefore,calling them chain isomers is incorrect.
$(D)$ Pent-$1$-ene and $2$-methylbut-$1$-ene are chain isomers because the parent carbon chain length changes from $5$ to $4$ carbons.
231
MediumMCQ
Match the column $I$ with column $II$.
Column $I$ (Compounds)Column $II$ (Relation)
$(i)$ $CH_3-CH_2-C(CH_3)_2-Cl$ and $(CH_3)_3C-Cl$$(P)$ Homologues
$(ii)$ $C_6H_5-O-CH_2-CH_3$ and $C_6H_5-O(CH_3)-CH_3$ (ortho-methylanisole)$(Q)$ Functional group isomers
$(iii)$ $C_6H_5-O-CH_3$ and $2-methylphenol$$(R)$ Metamers
$(iv)$ $CH_3-CH(CH_3)-CH_2-OH$ and $(CH_3)_3C-OH$$(S)$ Position isomers
A
$i-R, ii-S, iii-Q, iv-P$
B
$i-P, ii-Q, iii-R, iv-S$
C
$i-P, ii-R, iii-Q, iv-S$
D
$i-S, ii-R, iii-Q, iv-P$

Solution

(C) Step $1$: Analyze $(i)$. The compounds are $2-chloro-2-methylbutane$ and $2-chloro-2-methylpropane$. They differ by a $-CH_2-$ group,so they are Homologues $(P)$.
Step $2$: Analyze $(ii)$. The compounds are $ethoxybenzene$ and $1-methoxy-2-methylbenzene$. These are Metamers $(R)$ as the alkyl group attached to the oxygen atom changes.
Step $3$: Analyze $(iii)$. The compounds are $methoxybenzene$ $(ether)$ and $2-methylphenol$ $(alcohol)$. These have different functional groups,so they are Functional group isomers $(Q)$.
Step $4$: Analyze $(iv)$. The compounds are $2-methylpropan-1-ol$ and $2-methylpropan-2-ol$. The position of the $-OH$ group changes,so they are Position isomers $(S)$.
Therefore,the correct match is $i-P, ii-R, iii-Q, iv-S$.
232
MediumMCQ
Identify the relationship between the given Newman projections $I$,$II$,and $III$.
Question diagram
A
$I$ and $II$ are identical
B
$II$ and $III$ are chain isomers
C
$I$ and $III$ are positional isomers
D
$II$ and $III$ are identical

Solution

(C) The given structures are Newman projections of substituted ethanes. Let us convert them to their $IUPAC$ names:
$I$: $CH_3-CH(D)-CH_2(T)$ ($1$-tritio$-2-$deutero-propane)
$II$: $CH_3-CH(T)-CH_2(D)$ ($1$-deutero$-2-$tritio-propane)
$III$: $CH_3-CH_2-CH(DT)$ ($1$-deutero$-1-$tritio-propane)
Comparing the structures:
$I$ and $II$ are positional isomers because the positions of $D$ and $T$ atoms on the carbon chain are different.
$II$ and $III$ are positional isomers because the positions of $D$ and $T$ atoms are different.
$I$ and $III$ are positional isomers because the positions of $D$ and $T$ atoms are different.
None of the given options correctly describe the relationship. However,based on the provided options,if we re-evaluate the structures as isomers of the same molecular formula,they are all structural isomers. Given the standard nature of such questions,if $I$,$II$,and $III$ represent different substitution patterns on the same propane backbone,they are positional isomers.
233
EasyMCQ
Ether and alcohol are $\ldots \ldots$ isomers.
A
chain
B
position
C
functional
D
not isomers

Solution

(C) The general formula for both ethers and alcohols is $C_n H_{2n+2} O$.
In ethers,the functional group is an ether linkage $(-O-)$,while in alcohols,the functional group is a hydroxyl group $(-OH)$.
Since they possess different functional groups despite having the same molecular formula,they are classified as functional isomers.
234
MediumMCQ
Which among the following is a pair of functional isomers?
A
Butan-$2$-ol and $2$-Methylpropan-$1$-ol
B
Butan-$1$-ol and $1$-Methoxypropane
C
$1$-Methoxypropane and Ethoxyethane
D
$2$-Methoxypropane and $1$-Methoxypropane

Solution

(B) Functional isomers are compounds that have the same molecular formula but different functional groups.
In option $B$,Butan-$1$-ol $(C_4H_{10}O)$ is an alcohol,while $1$-Methoxypropane $(C_4H_{10}O)$ is an ether.
Since they have the same molecular formula but different functional groups ($-OH$ vs $-O-$),they are functional isomers.
235
EasyMCQ
Which of the following is a functional isomer of $pentan-2-ol$?
A
$Pentan-1-ol$
B
$Pentan-2-one$
C
$Ethoxypropane$
D
$Pentan-3-ol$

Solution

(C) $Pentan-2-ol$ $(C_5H_{12}O)$ is an alcohol.
Functional isomers are compounds with the same molecular formula but different functional groups.
$Ethoxypropane$ $(C_2H_5-O-C_3H_7)$ has the molecular formula $C_5H_{12}O$ and belongs to the ether functional group.
Therefore,$ethoxypropane$ is a functional isomer of $pentan-2-ol$.
$Pentan-1-ol$ and $pentan-3-ol$ are positional isomers,while $pentan-2-one$ is a ketone with the formula $C_5H_{10}O$.
236
EasyMCQ
Which of the following methods of structural formula representation conventionally uses a point for the front carbon and a circle around it for the rear carbon?
A
$A.$ Andiron formula
B
$B.$ Condensed formula
C
$C.$ Newman projection formula
D
$D.$ Fischer projection formula

Solution

(C) The correct answer is $C$.
In the Newman projection formula,the molecule is viewed along the $C-C$ bond axis.
The carbon atom nearer to the observer is represented by a point,and the rear carbon atom (further from the observer) is represented by a circle around that point.
237
EasyMCQ
Which of the following pairs of compounds exhibits metamerism?
A
$but-2-ene$ and $but-1-ene$
B
$Methoxymethane$ and $Ethanol$
C
$Ethoxyethane$ and $Methoxypropane$
D
$Butane$ and $2-Methylpropane$

Solution

(C) $Ethoxyethane$ $(CH_3-CH_2-O-CH_2-CH_3)$ and $methoxypropane$ $(CH_3-O-CH_2-CH_2-CH_3)$ have the same functional group (ether) but have a different distribution of carbon atoms attached to the ethereal oxygen atom. Thus,this pair of compounds exhibits metamerism.
238
MediumMCQ
Which of the following pairs of compounds is an example of position isomerism?
A
$2-$methylprop$-1-$ene and but$-1-$ene
B
but$-2-$ene and cis-but$-2-$ene
C
but$-2-$ene and $2-$methylprop$-1-$ene
D
but$-1-$ene and but$-2-$ene

Solution

(D) Position isomerism occurs when the position of a functional group or a double bond changes while the carbon skeleton remains the same.
In $CH_3-CH_2-CH=CH_2$ (but$-1-$ene),the double bond is at the $C-1$ position.
In $CH_3-CH=CH-CH_3$ (but$-2-$ene),the double bond is at the $C-2$ position.
Since the parent carbon chain is the same and only the position of the double bond differs,they are position isomers.
239
EasyMCQ
Which of the following pairs of compounds is an example of metamerism?
A
$n-$Butane and $2-$Methylpropane
B
Dimethyl ether and ethyl alcohol
C
but$-2-$ene and but$-1-$ene
D
Ethoxyethane and $1-$methoxypropane

Solution

(D) Metamerism arises due to the presence of different alkyl groups attached to the same polyvalent functional group (like $-O-$,$-S-$,$-NH-$,etc.).
In $Ethoxyethane$ $(CH_3CH_2-O-CH_2CH_3)$,the oxygen atom is attached to two ethyl groups.
In $1-Methoxypropane$ $(CH_3-O-CH_2CH_2CH_3)$,the oxygen atom is attached to a methyl group and a propyl group.
Since the alkyl groups attached to the oxygen atom are different,these compounds are metamers.
240
MediumMCQ
Which of the following pairs of alkenes is an example of position isomers?
A
$but-1-ene$ and $2-methylprop-1-ene$
B
$but-1-ene$ and $2-methylbut-1-ene$
C
$but-1-ene$ and $but-2-ene$
D
$but-2-ene$ and $2-methylprop-1-ene$

Solution

(C) Position isomers are compounds that have the same molecular formula but differ in the position of the functional group or multiple bond on the carbon chain.
In $but-1-ene$ $(CH_3-CH_2-CH=CH_2)$,the double bond is at the $1^{st}$ position.
In $but-2-ene$ $(CH_3-CH=CH-CH_3)$,the double bond is at the $2^{nd}$ position.
Since the position of the double bond is different while the carbon skeleton remains the same,they are position isomers.
241
EasyMCQ
Identify the isomerism exhibited by methoxyethane and propan-$1$-ol.
A
Position isomerism
B
Chain isomerism
C
Functional group isomerism
D
Metamerism

Solution

(C) The molecular formula for both methoxyethane $(CH_3-O-CH_2-CH_3)$ and propan-$1$-ol $(CH_3-CH_2-CH_2-OH)$ is $C_3H_8O$.
Methoxyethane is an ether,while propan-$1$-ol is an alcohol.
Since they have the same molecular formula but different functional groups,they exhibit functional group isomerism.
242
MediumMCQ
What type of isomers are $CH_3-CH_2-O-CH_2-CH_3$ (ethoxy ethane) and $CH_3-O-CH_2-CH_2-CH_3$ (methoxy propane)?
A
Tautomers
B
Metamers
C
Position isomers
D
Functional group isomers

Solution

(B) Metamerism arises due to the difference in the nature of alkyl groups attached to the same polyvalent functional group (in this case,the ether oxygen atom,$-O-$).
In $CH_3-CH_2-O-CH_2-CH_3$ (ethoxy ethane),the alkyl groups attached to the oxygen are two ethyl groups $(-C_2H_5)$.
In $CH_3-O-CH_2-CH_2-CH_3$ (methoxy propane),the alkyl groups attached to the oxygen are a methyl group $(-CH_3)$ and a propyl group $(-C_3H_7)$.
Since the distribution of alkyl groups around the oxygen atom is different,these compounds are metamers.
243
MediumMCQ
The number of structural isomers for the molecular formula $C_{4}H_{10}O$ is:
A
$7$
B
$8$
C
$6$
D
$5$

Solution

(A) The molecular formula $C_{4}H_{10}O$ corresponds to saturated acyclic compounds (alcohols and ethers). The structural isomers are as follows:
Alcohols:
$1$. $CH_{3}CH_{2}CH_{2}CH_{2}OH$ ($n$-butanol)
$2$. $CH_{3}CH_{2}CH(OH)CH_{3}$ (butan-$2$-ol)
$3$. $(CH_{3})_{2}CHCH_{2}OH$ (isobutanol)
$4$. $(CH_{3})_{3}COH$ (tert-butanol)
Ethers:
$5$. $CH_{3}OCH_{2}CH_{2}CH_{3}$ (methyl propyl ether)
$6$. $CH_{3}OCH(CH_{3})_{2}$ (methyl isopropyl ether)
$7$. $CH_{3}CH_{2}OCH_{2}CH_{3}$ (diethyl ether)
There are a total of $7$ structural isomers.
244
MediumMCQ
Which of the following is not an isomer of pentane?
A
$n$-pentane
B
$2,2$-dimethylpropane
C
$2,3$-dimethylbutane
D
$2$-methylbutane

Solution

(C) Pentane has the molecular formula $C_5H_{12}$. Isomers must have the same molecular formula but different structural arrangements.
$1.$ $n$-pentane: $CH_3-CH_2-CH_2-CH_2-CH_3$ $(C_5H_{12})$
$2.$ $2,2$-dimethylpropane: $CH_3-C(CH_3)_2-CH_3$ $(C_5H_{12})$
$3.$ $2$-methylbutane: $CH_3-CH(CH_3)-CH_2-CH_3$ $(C_5H_{12})$
$4.$ $2,3$-dimethylbutane: $CH_3-CH(CH_3)-CH(CH_3)-CH_3$ $(C_6H_{14})$
Since $2,3$-dimethylbutane has $6$ carbon atoms and the formula $C_6H_{14}$,it is an isomer of hexane,not pentane. Thus,option $C$ is correct.
245
MediumMCQ
The number of metamers possible for $C_{4}H_{10}O$ is
A
$1$
B
$2$
C
$3$
D
$4$

Solution

(C) Metamers are isomers that have the same molecular formula but differ in the distribution of alkyl groups on either side of the functional group (in this case,the ether oxygen atom).
For the molecular formula $C_{4}H_{10}O$,the possible ether metamers are:
$i$) $CH_{3}CH_{2}-O-CH_{2}CH_{3}$ (Diethyl ether)
$ii$) $CH_{3}-O-CH_{2}CH_{2}CH_{3}$ (Methyl propyl ether)
$iii$) $CH_{3}-O-CH(CH_{3})_{2}$ (Methyl isopropyl ether)
Thus,there are $3$ possible metamers.
246
DifficultMCQ
Compounds $P$ and $R$ in the following reaction are:
Question diagram
A
Position isomers
B
Functional isomers
C
Metamers
D
Chain isomers

Solution

(A) $1$. The reaction sequence is as follows:
$CH_3CHO \xrightarrow[(ii) H_3O^+]{(i) CH_3MgBr} CH_3-CH(OH)-CH_3 (P)$
$CH_3-CH(OH)-CH_3 \xrightarrow[\Delta]{conc. H_2SO_4} CH_3-CH=CH_2 (Q)$
$CH_3-CH=CH_2 \xrightarrow[(ii) H_2O_2/OH^-]{(i) B_2H_6} CH_3-CH_2-CH_2OH (R)$
$2$. Compound $P$ is propan$-2-$ol $(CH_3-CH(OH)-CH_3)$ and compound $R$ is propan$-1-$ol $(CH_3-CH_2-CH_2OH)$.
$3$. Both compounds have the same molecular formula $(C_3H_8O)$ and the same functional group $(-OH)$,but the position of the hydroxyl group is different (carbon-$2$ in $P$ and carbon-$1$ in $R$).
$4$. Therefore,$P$ and $R$ are position isomers.
247
MediumMCQ
In the reaction,as shown in the image,the number of possible isomers for the organic compound $X$ is
Question diagram
A
$4$
B
$5$
C
$3$
D
$2$

Solution

(D) The reaction is between isobutylmagnesium bromide and methylamine. The Grignard reagent acts as a base and abstracts the acidic proton from the amine to form an alkane.
$ (CH_3)_2CHCH_2MgBr + CH_3NH_2 \rightarrow (CH_3)_2CHCH_3 + Mg(Br)NHCH_3 $
The organic compound $X$ formed is isobutane,which is $2$-methylpropane,$(CH_3)_2CHCH_3$.
The molecular formula of $X$ is $C_4H_{10}$.
The isomers of $C_4H_{10}$ are:
$1$. $n$-butane: $CH_3-CH_2-CH_2-CH_3$
$2$. Isobutane ($2$-methylpropane): $CH_3-CH(CH_3)-CH_3$
Thus,there are $2$ possible isomers for the organic compound $X$.
248
EasyMCQ
Among the following,identify the compound that is not an isomer of hexane $(C_6H_{14})$:
A
$CH_3-CH_2-CH(CH_3)-CH_2-CH_3$
B
$CH_3-CH_2-CH_2-CH_2-CH_2-CH_3$
C
Ethylcyclobutane
D
$CH_3-CH(CH_3)-CH_2-CH_2-CH_3$

Solution

(C) Hexane is an alkane with the molecular formula $C_6H_{14}$. Isomers of hexane must also have the molecular formula $C_6H_{14}$.
$A$. $3$-methylpentane $(C_6H_{14})$ is an isomer.
$B$. $n$-hexane $(C_6H_{14})$ is an isomer.
$C$. Ethylcyclobutane has a ring structure,and its molecular formula is $C_6H_{12}$. Therefore,it is not an isomer of hexane.
$D$. $2$-methylpentane $(C_6H_{14})$ is an isomer.
Thus,the compound that is not an isomer of hexane is ethylcyclobutane.
249
EasyMCQ
$Propanone$ and $propanal$ are:
A
position isomers
B
functional isomers
C
chain isomers
D
geometrical isomers

Solution

(B) $Propanone$ $(CH_3COCH_3)$ and $propanal$ $(CH_3CH_2CHO)$ have the same molecular formula,$C_3H_6O$.
$Propanone$ contains a ketone functional group $(-CO-)$,whereas $propanal$ contains an aldehyde functional group $(-CHO)$.
Since they possess the same molecular formula but different functional groups,they are classified as functional isomers.
250
EasyMCQ
Which of the following is not a pair of functional isomers?
A
$C_{2}H_{5}OC_{2}H_{5}$ and $C_{3}H_{7}OCH_{3}$
B
$CH_{3}CH_{2}OH$ and $CH_{3}OCH_{3}$
C
$CH_{3}CH_{2}NO_{2}$ and $H_{2}NCH_{2}COOH$
D
$CH_{3}COOH$ and $HCOOCH_{3}$

Solution

(A) Functional isomers are compounds that have the same molecular formula but possess different functional groups.
In option $A$,both $C_{2}H_{5}OC_{2}H_{5}$ (diethyl ether) and $C_{3}H_{7}OCH_{3}$ (methyl propyl ether) contain the same functional group,which is an ether $(-O-)$. Therefore,they are metamers,not functional isomers.
In option $B$,$CH_{3}CH_{2}OH$ (alcohol) and $CH_{3}OCH_{3}$ (ether) are functional isomers.
In option $C$,$CH_{3}CH_{2}NO_{2}$ (nitroalkane) and $H_{2}NCH_{2}COOH$ (amino acid) represent different functional groups.
In option $D$,$CH_{3}COOH$ (carboxylic acid) and $HCOOCH_{3}$ (ester) are functional isomers.

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