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Basics of Organic Chemistry question

2025 · 3 Apr · Shift 2 · Q22
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Basics of Organic Chemistry question

2025 · 3 Apr · Shift 2 · Q22

JEE MainChemistryBasics of Organic ChemistryNumerical+4 / −1
The total number of structural isomers possible for the substituted benzene derivatives with the molecular formula C9H12\mathrm{C}_9 \mathrm{H}_{12}C9​H12​ is ‾\underline{\hspace{2cm}}​.
Numerical answer
View written solutionFree

Correct answer: 8

  1. Identify what kind of compounds are possible

A substituted benzene derivative has a benzene ring, i.e. a phenyl part contributing C6H5\mathrm{C_6H_5}C6​H5​ when one hydrogen is replaced.

Given molecular formula: C9H12\mathrm{C_9H_{12}}C9​H12​

Compare with benzene: C6H6\mathrm{C_6H_6}C6​H6​

So the substituents together must contribute:

  • Carbon increase: 9−6=39-6=39−6=3
  • Hydrogen increase: 12−6=612-6=612−6=6

Thus we need benzene derivatives containing 3 extra carbons total.

Also, degree of unsaturation check: IHD=2(9)+2−122=82=4\text{IHD} = \frac{2(9)+2-12}{2}=\frac{8}{2}=4IHD=22(9)+2−12​=28​=4 A benzene ring itself accounts for 4, so the side chain(s) must be saturated and acyclic.

So we only need to distribute 3 carbons as alkyl substituents on a benzene ring.


  1. Possible ways to distribute 3 carbons among substituents

The partitions of 3 are:

  1. 333
  2. 2+12+12+1
  3. 1+1+11+1+11+1+1

We count structural isomers for each case.


  1. Case 1: One 3-carbon substituent

This gives propylbenzene type compounds.

A 3-carbon alkyl group can attach to benzene in two different ways:

  • n-propylbenzene: C6H5CH2CH2CH3\mathrm{C_6H_5CH_2CH_2CH_3}C6​H5​CH2​CH2​CH3​
  • isopropylbenzene (cumene): C6H5CH(CH3)2\mathrm{C_6H_5CH(CH_3)_2}C6​H5​CH(CH3​)2​

So, number of isomers in this case: 222


  1. Case 2: One ethyl and one methyl substituent

This is ethylmethylbenzene.

For a disubstituted benzene with two different substituents, the distinct positional isomers are:

  • ortho (1,2)(1,2)(1,2)
  • meta (1,3)(1,3)(1,3)
  • para (1,4)(1,4)(1,4)

So we get:

  • ooo-ethyltoluene
  • mmm-ethyltoluene
  • ppp-ethyltoluene

Hence number of isomers in this case: 333


  1. Case 3: Three methyl substituents

This gives trimethylbenzene.

Distinct positional arrangements of three identical methyl groups on benzene are:

  • 1,2,31,2,31,2,3-trimethylbenzene
  • 1,2,41,2,41,2,4-trimethylbenzene
  • 1,3,51,3,51,3,5-trimethylbenzene

So number of isomers in this case: 333


  1. Total number of structural isomers

Adding all cases: 2+3+3=82+3+3=82+3+3=8

So the total number of structural isomers is: 8\boxed{8}8​


  1. Comparison with stored answer

Stored correct answer = 888

Our derived answer = 888

Hence, they agree.

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