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Why Does Benzene Undergo Electrophilic Substitution Reactions Easily and Nucleophilic Substitutions with Difficulty? - Chemistry

Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?

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Solution 1

Due to the presence of an electron cloud containing 6 n-electrons above and below the plane of the ring, benzene is a rich source of electrons. Consequently, it attracts the electrophiles (electron-deficient) reagents towards it and repels nucleophiles (electron- rich) reagents. As a result, benzene undergoes electrophilic substitution reactions easily and nucleophilic substitutions with difficulty.

Solution 2

Benzene is a planar molecule having delocalized electrons above and below the plane of ring. Hence, it is electron-rich. As a result, it is highly attractive to electron deficient species i.e., electrophiles.

Therefore, it undergoes electrophilic substitution reactions very easily. Nucleophiles are electron-rich. Hence, they are repelled by benzene. Hence, benzene undergoes nucleophilic substitutions with difficulty.

Concept: Chemical Properties of Aromatic Hydrocarbons
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APPEARS IN

NCERT Class 11 Chemistry Textbook
Chapter 13 Hydrocarbons
Q 19 | Page 397
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