Which of the following correctly ranks the substituents nitro (), methyl (), and methoxy () on a benzene ring in order of increasing electron-donating ability?
A
Nitro Methoxy Methyl
B
Methoxy Methyl Nitro
C
Nitro Methyl Methoxy
D
Methyl Nitro Methoxy
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검증된 단계별 안내
1
Step 1: Understand the nature of each substituent on the benzene ring in terms of their electron-donating or electron-withdrawing effects. The nitro group (\( \mathrm{NO_2} \)) is a strong electron-withdrawing group due to its resonance and inductive effects, the methyl group (\( \mathrm{CH_3} \)) is a weak electron-donating group through hyperconjugation, and the methoxy group (\( \mathrm{OCH_3} \)) is a strong electron-donating group due to resonance donation of lone pairs on oxygen.
Step 2: Recall that electron-withdrawing groups decrease electron density on the benzene ring, while electron-donating groups increase it. Therefore, the nitro group will have the least electron-donating ability (actually electron-withdrawing), methyl will have moderate electron-donating ability, and methoxy will have the highest electron-donating ability.
Step 3: Rank the substituents from least to greatest electron-donating ability based on their electronic effects: nitro (strongly withdrawing) < methyl (weakly donating) < methoxy (strongly donating).
Step 4: Express this ranking using the inequality notation: \( \mathrm{NO_2} < \mathrm{CH_3} < \mathrm{OCH_3} \), where the symbol \( < \) means 'less electron-donating than'.
Step 5: Confirm that this order matches the known chemical behavior of these substituents on aromatic rings, which is important for predicting reactivity and directing effects in electrophilic aromatic substitution reactions.