Substituents on an aromatic ring can have several effects on electrophilic aroma

Question

Substituents on an aromatic ring can have several effects on electrophilic aromatic substitution reactions. Substituents can activate or deactivate the ring to substitution, donate or withdraw electrons inductively, donate or withdraw electrons through resonance, and direct substitution either to the ortho/para or to the meta positions. From the following lists, select the substituents that have the indicated property. The substituents are written as -XY, where X is the atom directly bound to the aromatic ring.

bstituents on an aromatic ring can have several effects on electrophilic aromatic substitution reactions ubstituents can activate or deactivate the ring to substitution, donate or withdraw electrons inductively donate or withdraw electrons through resonance, and direct substution either to the ortho/para or to the meta positions. From the following lists, select the substituents that have the indicated property. The substituents are written as -XY X is the atom directly bound to the aromatic ring Activation of the ring towards substitution. Withdrawal of electrons through resonance Ortho para-directed substitution SO3H -CI OCoCH3 -COOH Br NHCOCH3 -NO2

Explanation / Answer

The group which can donate electron by mesomeric effect are +M groups, they are ortho para directing group

The group which can show +I effect are ring activating groups.

The group which can pull electrons from the ring are meta directing group and are deactivating as well

golden rule: the groups with multiple bond are deactivating groups (meta directing)

The general categorization will be

a) o,p directing and activating : OH , NH2 , CH3, OCH3 , OCOCH3, NHCOCH3, C6H5

b) o-p directing but deactivating: halogens

c) metal directing deactivating : COOH , CHO , NO2, CN, SO3H

Hope it will help you

The correct answers will be

(i) activation of the ring towards substitution: NH2, OCOCH3

(ii) withdrawal of electrons through resonance: CN , COOH

(iii) orhto para directed : Br , NHCOCH3 , OCOCH3

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