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Rank each of the following compounds in decreasing order of reactivity towards Friedel-Crafts alkylation. Most reactive...

Rank each of the following compounds in decreasing order of reactivity towards Friedel-Crafts alkylation. Most reactive = 1; if a compound will not react, rank it as "non" rather than assigning a numerical value. Compound A: bromobenzene Compound B: aniline Compound C: anisole Compound D: iodobenzene

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Friedel-Crafts Alkylation is an aromatic electrophilic substitution reaction in which a positively charged electrophilic alkyl group gets substituted on to the aromatic ring and forms an alkylated product. For this reaction, the aromatic ring should be enriched with the negatively charged electrons In the Friedel-Crafts Alkylation, the reactivity of the given compounds can be realized by the nature and effect of the substituents attached on the aromatic ring If the substituent is electron donat activates the aromatic ring by making it more attractive to the approaching electrophilic element. Thus the whole compound becomes more reactive in the Friedel-Crafts Alkylation reaction. ing group, then it can donate electrons to the aromatic ring and If the substituent is electron withdrawing group, then it cannot donate electrons to the aromatic ring, instead it will withdraw the electron towards it and deactivates the aromatic ring by making it less attractive to the approaching electrophilic element. Thus the whole compound becomes less reactive in the Friedel-Crafts Alkylation reaction. The following table summarizes the above discussion Compound Structure Substituent Electron Electron Electron Activator/Deactivator Reactivity in the Attached donating/ Friedel-Crafts Alkylation withdrawing Compound A, Brom ob enzene Br Activator Reactive-3 donating NH Compound B, Aniline Electron donating NH2 Deactivator Non-reactive Compound C, Anisole Electron donating Reactive-Most- reactive-l Activator Compound D Iodobenzene Electron withdrawing Activator Reactive-2

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