1 Lecture No.38 Electrophilic Aromatic Substitution Reactions • At the end of this lecture, student will be able to – Discuss the concept of aromaticity and Huckel’s rule – Differentiate aromatic and nonaromatic compounds – Explain the general mechanism of electrophilic aromatic substitution reaction – List out examples for EAS reactions
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• At the end of this lecture, student will be able to
– Discuss the concept of aromaticity and Huckel’s rule– Differentiate aromatic and nonaromatic compounds– Explain the general mechanism of electrophilic aromatic
substitution reaction– List out examples for EAS reactions
Criteria for Aromaticity• A molecule must have uninterrupted cyclic cloud of π electrons• For the π cloud to be cyclic, the molecule must be cyclic• For the π cloud to be uninterrupted, every atom in the ring must have a p-orbital• For the π cloud to form, each p orbital must overlap with the p orbitals on either side of
it• Therefore, the molecule must be planar• Odd number of pairs of π electrons• Huckel’s rule or 4n + 2 rule states that for a planar, cyclic compound to be aromatic its
uninterrupted π cloud must contain (4n+2) π electrons, where n is any whole number (0,1,2,…)
• Benzene – planar and resonance stabilized• Huckel’s rule states that for a planar, cyclic compound to be
aromatic its uninterrupted π cloud must contain (4n+2) π electrons, where n is any whole number (0,1,2,…)
• Benzene undergoes electrophilic aromatic substitution reactions• Sigma complex is formed which is resonance stabilized• Nitration, sulphonation, halogenation, Friedel Craft’s alkylation and
Friedel Craft’s acylation of benzene are electrophilic substitution reactions