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Problem 1 - Olympiad

Which of the following compounds will undergo Friedel-Crafts alkylation most readily with CH3Cl and AlCl3?

Correct: D

p-Fluoroanisole (C6H5OCH3 with -F) has the least deactivating group due to +R effect of -OCH3 and -I effect of -F being weaker than other halogens. Electron-rich aromatic rings undergo Friedel-Crafts more easily.