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Question #45088
The Question
An aromatic compound, 1-chloro-3-methylbenzene, undergoes electrophilic aromatic substitution using a nitrating mixture (conc. and conc. ) at under kinetic control. Among the possible mono-nitrated isomers, a specific isomer is formed as the predominant major product due to the overriding influence of a distance-dependent electronic effect. Identify the correct IUPAC name of product .
Options
- A.
4-chloro-2-methyl-1-nitrobenzene
- B.
2-chloro-4-methyl-1-nitrobenzene
- C.
1-chloro-3-methyl-2-nitrobenzene
- D.
1-chloro-3-methyl-5-nitrobenzene
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Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Mechanism_Trap
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Concepts Behind This Question
Reaction Intermediates Stability|Inductive Effect Trends|Electrophilic Substitution Orientation
Why This Question Is Tricky
Common Mistakes
This problem tests a critical exception to standard electrophilic aromatic substitution rules.
Students typically learn that activating groups direct para due to steric hindrance at the ortho position.
In 1-chloro-3-methylbenzene, this logic incorrectly predicts substitution at C6 (para to methyl).
The hidden variable is the strong, distance-dependent Inductive Effect (-I) of the halogen.
Because C6 is ortho to the chlorine atom, the -I effect severely destabilizes the sigma-complex at this position.
Consequently, the reaction is forced to occur at C4 (ortho to methyl, but para to chlorine), overriding the standard steric preference.
This highlights the dominance of electronic destabilization over steric factors in ortho-halo substituted transition states.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Organic Chemistry – Some Basic Principles and Techniques - Class 11 Part 2 |
| Concept | Reaction Intermediates Stability |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |