Electron-Donating and Electron-Withdrawing Groups

identify each as a strong, moderate, or weak activator or deactivator and which direction it gives

alcohol

strong activator (ortho-para)

oxygen

strong activator (ortho-para)

NH2

strong activator (ortho-para)

N with 2 R groups attached to benzene

strong activator (ortho-para)

benzene-O-R

moderate activator (ortho-para)

benzene-O of ester-R

moderate activator (ortho-para)

benzene-NH of amide-R

moderate activator (ortho-para)

benzene-NR of amide-R

moderate activator (ortho-para)

halogens (chlorine, bromine, iodine)

weak deactivator (ortho-para)

alkyl R groups

weak activator (ortho-para)

ketone

moderate deactivator (meta)

benzene-carbonyl carbon of aldehyde

moderate deactivator (meta)

benzene-Carbonyl carbon of ester-R

moderate deactivator (meta)

benzene-carbonyl carbon of carboxylic acid

moderate deactivator (meta)

benzene-carbonyl carbon of amide

moderate deactivator (meta)

benzene-sulfonic acid

moderate deactivator (meta)

benzene-carbon of nitrile

moderate deactivator (meta)

benzene-NO2

strong deactivator (meta)

benzene-N+R3

strong deactivator (meta)

benzene-CBr3

strong deactivator (meta)

electron donating groups are

activators (except for halogens)

electron withdrawing groups are

deactivators