Organic Chemistry 2 · Substituent effects and directing
Direction is not activation
Conditions: Compare chlorobenzene with benzene in an otherwise matched electrophilic aromatic substitution.
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The question
Which qualitative statement is appropriate?
Reveal the answer and explanation
Answer and explanation
Correct answer Chlorobenzene is deactivated but ortho/para directing.
Inductive withdrawal reduces overall reactivity while lone-pair resonance donation favors those positions.
Not this one Chlorobenzene is activated because every ortho/para director activates.
Rate and positional selectivity are different comparisons.
Not this one Chlorobenzene is meta directing because chlorine withdraws inductively.
This overlooks the positional effect of halogen resonance donation.
Worked solution
Chlorine’s electronegativity lowers ring reactivity through induction. Its lone pairs still contribute additional stabilization to ortho/para σ complexes relative to meta ones. The two effects can coexist without contradiction.
What you'll practice
Classify the rate and positional effects of chlorine separately.
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