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 may be electronically favored.

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 may be electronically favored. Why?

Prashant Kotian · Accepted Answer

Correct answer: C. This follows the "Steric Sandwich" rule. Even if a position between two meta groups is electronically activated, electrophiles generally cannot attack it due to extreme physical space constraints (steric hindrance).

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