Polynuclear aromatics (intro)
Hydrocarbons · Chemistry
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Why is naphthalene more reactive than benzene in EAS? Step 1: Naphthalene's resonance energy per ring (~127 kJ/mol) < benzene's 150. Step 2: EAS disrupts one ring's aromaticity but leaves the other intact. Step 3: Less aromaticity lost in the arenium ion → lower activation energy. Step 4: α-position preferred (arenium keeps one full benzene ring). Reactivity explained!
Related topics
- Alkanes: preparation (Wurtz, Kolbe, decarboxylation), free-radical halogenation
- Alkenes: preparation (dehydration, dehydrohalogenation), electrophilic addition, Markovnikov's rule, peroxide effect
- Alkynes: preparation, acidic character, addition reactions
- Aromatic hydrocarbons: benzene structure, aromaticity and Huckel's rule
- Electrophilic aromatic substitution: nitration, sulfonation, halogenation, Friedel–Crafts
- Directing effects of substituents