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Magazine Chapter 18: Q 51. (page 723)
Question: Using resonance structures, explain why a nitroso group (-NO) is an ortho, para director that deactivates a benzene ring toward electrophilic attack.
Short Answer
Answer
Step by step solution
Resonance structures
The Lewis structures used to represent the movement of electrons in a pi bonded system are named resonance structures.
Electrophile
Electrophiles are electron-deficient species that get attracted to electron-rich centers.
The presence of electron-withdrawing groups on a system decreases their reactivity towards electrophiles.
Resonance structures of nitroso benzene
The nitroso group (-NO) on a benzene ring acts as a deactivating group. It pulls the pi-electron density from the ring, generating electron deficiencies (indicated using the positive charge) on ortho and para positions.
Resonance structures of nitrosobenzene
Since the presence of the nitroso group reduces the electron density of the ring, it deactivates the benzene ring towards electrophilic attack.
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