Out of benzene, m-dinitrobenzene and toluene which will undergo nitration most easily and why?
Solution and Explanation
The ease of nitration depends on the presence of electron density on the compound to form nitrates. Nitration reactions are examples of electrophilic substitution reactions where an electron-rich species is attacked by a nitronium ion (NO2-).
Now, CH3 - group is electron donating and NO2- is electron withdrawing. Therefore, toluene will have the maximum electron density among the three compounds followed by benzene. On the other hand, m - Dinitrobenzene will have the least electron density. Hence, it will undergo nitration with difficulty. Hence, the increasing order of nitration is as follows:
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Concepts Used:
Aromatic hydrocarbon
Aromatic hydrocarbons, sometimes known as arenes, are aromatic organic molecules made up entirely of carbon and hydrogen. In aromatic compounds a benzene ring which is named after the simple aromatic chemical benzene, or a phenyl group when part of a larger structure, is the configuration of six carbon atoms.
Read More: Aromaticity
Reactions of Aromatic Hydrocarbons:
1. Aromatic Substitution Reactions
This reaction involves the replacement of one substituent on the ring of an aromatic hydrocarbon, commonly a hydrogen atom, by a different substituent group.
The common types of aromatic substitution reactions are:
- Nucleophilic aromatic substitution reactions
- Electrophilic aromatic substitution reactions
- Radical nucleophilic aromatic substitution reactions
2. Coupling Reactions
In these types of reactions, the coupling of two fragments that have a radical nature is achieved with the help of a metal catalyst