MindMap Gallery Organic Chemistry Aromatic Hydrocarbons
Compilation of knowledge on aromatic hydrocarbons in organic chemistry, including benzene and its homologues, polycyclic aromatic hydrocarbons, and non-benzene aromatic hydrocarbons. Friends who like it can give it a like!
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Avatar 3 centers on the Sully family, showcasing the internal rift caused by the sacrifice of their eldest son, and their alliance with other tribes on Pandora against the external conflict of the Ashbringers, who adhere to the philosophy of fire and are allied with humans. It explores the grand themes of family, faith, and survival.
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Aromatic hydrocarbons
Benzene and its homologues
Classification
Monocyclic aromatic hydrocarbons
polycyclic aromatic hydrocarbons
Polyphenyl aliphatic hydrocarbons
biphenyl aromatic hydrocarbons
Condensed aromatic hydrocarbons
name
The structure of benzene
Kekule structural formula
Alternating single and double bonds
shortcoming
There are three double bonds in the molecule, which should have the properties of an alkene, but its chemical properties are very stable.
Ortho disubstituted benzene should have two isomers, but in fact only one
There are three carbon-carbon double bonds and three carbon-carbon single bonds in the benzene ring. The bond lengths should be different, so the benzene ring is not a regular hexagon. However, experiments have shown that the benzene ring is a regular hexagonal structure. The carbon atoms in the ring are The bond lengths are exactly the same
The heat of hydrogenation is not three times that of cyclohexene, indicating that the benzene ring is not composed of three double bonds, but is a more stable substance than cyclohexene.
aromatic sextet
Benzene is a regular hexagonal planar molecule with average bond lengths and bond angles.
The molecule has a closed major bond
π electrons are highly delocalized, so the energy of the system is low, and benzene has special stability
Isomerism and naming of benzene homologues
After a hydrogen atom in an aromatic hydrocarbon molecule is removed, the remaining atomic group is an aryl group, represented by Ar
When -R, -X, -NO2 is connected to benzene, benzene is used as the parent, and the name of the substituent is written in front of the parent, which is called a certain benzene.
When there are -OH, -NH2, -SO3H, -CHO, -COOH on the benzene ring, these functional groups are used as the parent
When a complex, longer or unsaturated chain hydrocarbon is connected, benzene is used as the substituent and the chain hydrocarbon is used as the parent.
Physical properties of benzene and its homologues
It is generally a colorless liquid with fragrance, flammable, insoluble in water, and easily soluble in organic solvents or non-polar solvents.
Have certain toxicity
Chemical properties of benzene and its derivatives
Electrophilic substitution reaction on benzene ring
nitrification reaction
Sulfonation reaction
Halogenation reaction
Friedel-Crafts reaction
Friedel-Crafts reaction
addition reaction
Ni catalyzes the change of cyclohexane by adding H2 at high temperature and high pressure
UV 50℃ plus Cl2 becomes 666
oxidation reaction
Oxidation reactions of benzene and its homologues
Oxidation of benzene
Catalyst V2O5 produces maleic anhydride
Side chain oxidation
Oxidizing agent: potassium permanganate, potassium dichromate
Oxidation rules
Regardless of the length of the branch chain, oxidation yields benzoic acid
No matter how many branches there are, oxidation will generate formic acid at the position of the original branch chain.
Branched chains that do not contain α-H cannot be oxidized
application
Synthetically introduce a carboxyl group into the benzene ring
Can qualitatively detect the position of benzene branch substituted by polyhydric hydrocarbons
replacement positioning rules
Positioning rules of electrophilic substitution reactions on aromatic rings
Ortho and para positioning bases
meta positioning base
The localization rules of electrophilic substitution reaction of disubstituted benzene
application
polycyclic aromatic hydrocarbons
Condensed aromatic hydrocarbons
Naphthalene
Anthracene and phenanthrene and other condensed ring aromatic hydrocarbons
non-benzene aromatic hydrocarbons
Huecker's rule
Directionality of nonbenzene aromatic hydrocarbons
Aromaticity of cyclic positive and negative ions
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annulene