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Correct answer: 8
- Identify what kind of compounds are possible
A substituted benzene derivative has a benzene ring, i.e. a phenyl part contributing when one hydrogen is replaced.
Given molecular formula:
Compare with benzene:
So the substituents together must contribute:
- Carbon increase:
- Hydrogen increase:
Thus we need benzene derivatives containing 3 extra carbons total.
Also, degree of unsaturation check: 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.
- Possible ways to distribute 3 carbons among substituents
The partitions of 3 are:
We count structural isomers for each case.
- 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:
- isopropylbenzene (cumene):
So, number of isomers in this case:
- 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
- meta
- para
So we get:
- -ethyltoluene
- -ethyltoluene
- -ethyltoluene
Hence number of isomers in this case:
- Case 3: Three methyl substituents
This gives trimethylbenzene.
Distinct positional arrangements of three identical methyl groups on benzene are:
- -trimethylbenzene
- -trimethylbenzene
- -trimethylbenzene
So number of isomers in this case:
- Total number of structural isomers
Adding all cases:
So the total number of structural isomers is:
- Comparison with stored answer
Stored correct answer =
Our derived answer =
Hence, they agree.
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