Directing effects of substituents
Hydrocarbons · Chemistry
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Predict nitration products of phenol vs nitrobenzene. Step 1: –OH is +M, strongly activating, o/p-directing → o- and p-nitrophenol (fast, mild conditions). Step 2: –NO₂ is –M, deactivating, m-directing → m-dinitrobenzene (needs vigorous conditions). Step 3: Existing substituent commands both rate and position. Step 4: Directing effects predict the major product every time!
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
- Polynuclear aromatics (intro)