Which one of the following is most reactive towards electrophilic reagent?
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Answer
(2) [figure]
Solution
Each compound has a -CH3 group; the reactivity towards an electrophile depends on the second group.
-OH: strong +R effect (lone pair on O delocalised into the ring) strongly activating.
-OCH3: +R effect, but slightly weaker than -OH.
-NHCOCH3: the lone pair on N is also delocalised over the C=O group only moderately activating.
-CH2OH: no lone pair on the atom attached to the ring only weakly activating (like an alkyl group).
Electron density in the ring is highest in o-cresol (2-methylphenol), so it is the most reactive towards electrophiles.
Answer: (2)