-CH2OH meta or o/p director

[luisfigo]

Working a problem that adds Br2/FeBr3 in EAS to a benzene ring with -CH2OH attached, and the answer says that the -CH2OH is an ortho/para director. Also from princeton review.

I was under the impression that a carbon attached to a more electronegative atom was a deactivating meta director, as in the case of -COOH. However an R group without a more electronegative atom attached is electron donating o/p director.

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[kimball]

Same reason as to why halogens are EWG but direct O/P, in this case resonance>induction

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[DAT Destroyer]

Working a problem that adds Br2/FeBr3 in EAS to a benzene ring with -CH2OH attached, and the answer says that the -CH2OH is an ortho/para director. Also from princeton review.

I was under the impression that a carbon attached to a more electronegative atom was a deactivating meta director, as in the case of -COOH. However an R group without a more electronegative atom attached is electron donating o/p director.

Focus what is DIRECTLY attached to the ring. Here it is a carbon. This is an ortho-para director. Undergrads never totally understand this, but I will spell it out for you. If you see a SINGLE bonded Oxygen or Nitrogen directly attached to a benzene ring, it will be an Activating group and direct ortho/para. Examples include groups like OH, NH2, OCH3, OC2H5 etc. These groups stabilize the intermediate Arenium ion in the mechanism. If you see a CARBONYL group such as an aldehyde, ketone, or even a COOH group, you are dealing with a deactivating group that will direct META. A deactivating group removes electron density from the intermediate Arenium ion and destabilizes it. Do yourself a huge favor, and consult a standard Organic Chemistry text written by a PhD in Organic Chemistry. I suggest the text by Dr. David Klein. The text will clearly show you the intermediates that I have spoken about.

Hope this helps.