Benzyl alcohol vs. Phenol

[MedHopeful234]

Hey Guys,

Does the CH2-OH group on benzylic alcohol make the benzene more reactive or less reactive compared to a phenol? I thought benzyl alcohol was more electron donating than phenol because of the extra CH2 in there (Since CH3 is electron donating/activating). But evidently benzylic alcohols are less reactive.

Is it safe to say that when a benzene is directly attached to a group via a carbon then an O it is deactivating and if it is first attached to an O then a R group it is activating?

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[jayoh]

Hey Guys,

Does the CH2-OH group on benzylic alcohol make the benzene more reactive or less reactive compared to a phenol? I thought benzyl alcohol was more electron donating than phenol because of the extra CH2 in there (Since CH3 is electron donating/activating). But evidently benzylic alcohols are less reactive.

Is it safe to say that when a benzene is directly attached to a group via a carbon then an O it is deactivating and if it is first attached to an O then a R group it is activating?

The reason the benzyl alcohol is less reactive than phenol has to do with the pi electrons on the oxygen. in the phenol molecule, the extra electrons can contribute to the aromatic pi system, but in benzyl alcohol they can't because they are next to a sp3 carbon which doesn't allow any overlap.

 

[Dotoday]

OH grou is more electron donating that CH2. So, phenol is more reactive.

 

[MedHopeful234]

Thanks guys!