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Question
Chemistry
Posted 3 months ago
8 Compound: Quinoline.
Theoretically, state the maximum number for the compound above to undergo electrophilic aromatic substitution reaction.
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Answer from Sia
Posted 3 months ago
Solution
1
Identify the structure of Quinoline: Quinoline is a heterocyclic aromatic compound with a structure that includes a benzene ring fused to a pyridine ring. In the benzene ring, there are five hydrogen atoms that can potentially be substituted in an electrophilic aromatic substitution (EAS) reaction. In the pyridine ring, due to the electron-withdrawing nature of the nitrogen atom, the positions that are ortho and para to the nitrogen are less reactive towards EAS
2
Determine the number of reactive positions: The benzene ring has five hydrogens that can be substituted. The pyridine ring has two positions ortho to the nitrogen and one position para to the nitrogen, but these are less likely to be involved in EAS due to the electron-withdrawing effect of the nitrogen. Therefore, the maximum number of EAS reactions Quinoline can theoretically undergo is primarily on the benzene ring
Answer
5
Key Concept
Electrophilic Aromatic Substitution (EAS) Reactivity
Explanation
Quinoline can theoretically undergo a maximum of five electrophilic aromatic substitution reactions, which occur on the benzene ring due to the decreased reactivity of the pyridine ring caused by the electron-withdrawing nitrogen atom.

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