When an electrophile attacks m-chlorotoluene, substitution at the position directly between the chlorine and methyl groups (position 2) is extremely rare, even though it is electronically favored. Why

Question

When an electrophile attacks m-chlorotoluene, substitution at the position directly between the chlorine and methyl groups (position 2) is extremely rare, even though it is electronically favored. Why?

Prashant Kotian · Accepted Answer

Correct answer: C. Poly-substitution Rule 3 (The Steric Sandwich): Even if a position between two meta groups is electronically activated, electrophiles generally cannot attack it due to the physical space constraints (steric hindrance).

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