List the following compounds in order from greatest tendency to least tendency t

Question

List the following compounds in order from greatest tendency to least tendency to undergo nucleophilic aromatic substitution. chlorobenzene, 2-chloro-1,3-dicyanobenzene, o-chlorocyanobenzene

List the following compounds in order from greatest tendency to least tendency to undergo nucleophilic aromatic substitution.
chlorobenzene, 2-chloro-1,3-dicyanobenzene, o-chlorocyanobenzene

o-chlorocyanobenzene > 2-chloro-1,3-dicyanobenzene > chlorobenzene

Part B

List the same compounds in order from greatest tendency to least tendency to undergo electrophilic aromatic substitution.

2-chloro-1,3-dicyanobenzene > o-chlorocyanobenzene > chlorobenzene o-chlorocyanobenzene > chlorobenzene > 2-chloro-1,3-dicyanobenzene 2-chloro-1,3-dicyanobenzene > chlorobenzene > o-chlorocyanobenzene chlorobenzene > 2-chloro-1,3-dicyanobenzene > o-chlorocyanobenzene chlorobenzene > o-chlorocyanobenzene > 2-chloro-1,3-dicyanobenzene

o-chlorocyanobenzene > 2-chloro-1,3-dicyanobenzene > chlorobenzene

Part B

List the same compounds in order from greatest tendency to least tendency to undergo electrophilic aromatic substitution.

chlorobenzene > 2-chloro-1,3-dicyanobenzene > o-chlorocyanobenzene 2-chloro-1,3-dicyanobenzene > chlorobenzene > o-chlorocyanobenzene 2-chloro-1,3-dicyanobenzene > o-chlorocyanobenzene > chlorobenzene o-chlorocyanobenzene > 2-chloro-1,3-dicyanobenzene > chlorobenzene o-chlorocyanobenzene > chlorobenzene > 2-chloro-1,3-dicyanobenzene chlorobenzene > o-chlorocyanobenzene > 2-chloro-1,3-dicyanobenzene

Explanation / Answer

part A ) answer :   2-chloro-1,3-dicyanobenzene > o-chlorocyanobenzene > chlorobenzene

explanation :  

chlorine , cynaide are electron withdrawing groups. number of withdrawing groups increases on benzene nucleophlic substitution reactivity also increases.

part B) answer : chlorobenzene > o-chlorocyanobenzene > 2-chloro-1,3-dicyanobenzene

explanation:

this is reverse of above one number of withdwaring groups increases electronphilic aromatic substitution decreases.

2-chloro-1,3-dicyanobenzene has two CN strong withdrawing groups . so reactivity lesser

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