Product variants?
Why can't the reaction between 1,2-dichloro-4-nitrobenzene and NaOMe produce the product 1-chloro-2-methoxy-4-nitrobenzene?
Which product is then formed instead?
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Die Nitrogruppe an einem Benzolring wirkt bei der elektrophilen Substitution meta-dirigierend, weil sie über die mesomeren Zustände die Elektronendichte in ortho- und para-Position vermindert. Nur haben wir es hier mit einer nukleophilen aromatischen Substitution zu tun, wo der Angriff des Nukleophils Methanolat natürlich bevorzugt an genau den Stellen erfolgt, wo die Elektronendichte gering ist. Daher wird das zur Nitrogruppe para-ständige Chlor ersetzt und nicht das Chlor in meta-Position.
Also ist das Produkt 2-Chlor-1-methoxy-4-nitrobenzol.
Genau.