MindMap Gallery Chemistry-Aromatic Hydrocarbons Mind Map
Knowledge summary of aromatic hydrocarbons chapter in university organic chemistry, including classification of aromatic hydrocarbons, reactions of aromatic hydrocarbon side chains, positioning rules of electrophilic substitution, etc.
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This is a mind map about bacteria, and its main contents include: overview, morphology, types, structure, reproduction, distribution, application, and expansion. The summary is comprehensive and meticulous, suitable as review materials.
This is a mind map about plant asexual reproduction, and its main contents include: concept, spore reproduction, vegetative reproduction, tissue culture, and buds. The summary is comprehensive and meticulous, suitable as review materials.
This is a mind map about the reproductive development of animals, and its main contents include: insects, frogs, birds, sexual reproduction, and asexual reproduction. The summary is comprehensive and meticulous, suitable as review materials.
Aromatic hydrocarbons
Classification of aromatic hydrocarbons
Benzene and benzene homologues
polycyclic aromatic hydrocarbons
polyphenyl aliphatic hydrocarbons
biphenyl
Condensed aromatic hydrocarbons
nonaromatic hydrocarbons
A carbocyclic compound that does not contain a benzene ring but has the characteristic "aromatic" nature of benzene
name
neighbor pair
The small group is located at position 1
Common substituents
Ph-phenyl
Ar-aryl
Tol-tolyl
Bz- Benzyl (phenylmethyl)
Functional group naming order book p146
benzene
The structure of benzene
Valence bond theory and molecular orbital theory
C atom sp2 hybridization, the p orbital not participating in the hybridization forms a large Π bond
Aromaticity
Carbon atoms are sp2 hybridized to form cyclic compounds
ring atoms coplanar
The number of Π electrons follows the 4n 2 rule
chemical properties
Halogenation
Replaced by bromine or chlorine under the catalysis of iron or iron salts
Nitrification
Electrophile: NO2
Concentrated nitric acid and concentrated sulfuric acid are heated together
sulfonation
Electrophile: SO3
is a reversible reaction
Sulfonic acid can be used to temporarily occupy the para position on the ring to prevent it from being substituted by other groups.
Friedel-Crafts reaction
Friedel-Crafts alkylation
There is rearrangement
It is difficult to prepare linear alkylbenzenes
Offensive reagent: carbocation
Lewis acid as catalyst reversible reaction
Friedel-Crafts acylation
No rearrangement
Generate aromatic ketones under the catalysis of aluminum trichloride
meta positioning base irreversible
Havus synthesis--preparation of fused ring compounds
Chloromethylation
Chloroformaldehyde, hydrogen chloride react under the catalysis of anhydrous zinc chloride p161
Reactions of aromatic side chains
Halogenation reaction
α-H reaction
Side chain oxidation reaction
Positioning rules for electrophilic substitution
Two types of positioning groups
The first type of positioning base (ortho position)
-NR2 -NHR -NH2 -OH -OR -NHCOR -OCOR -R -C6H5 -X
The second type of positioning base (meta position)
-NR3 -NO2 -CCl3 -CN -SO3H -CHO -COR -CO2R -CONH2
Activation and passivation
Strong activation
-NH2 -NHR -NR2 -OH
medium activation
-NHCOR -OR -OCOR
weak activation
-R -Ar
Weak passivation
-F -Cl -Br -I
passivation
-NR3 -NO2 -CF3 -CN -SO3H -CHO -COR -COOH -COOR -CONH2
Positioning rules for disubstituted benzene
consistent
obey
The positioning effects of the two substituents on the third substituent are different: determined by the first type of substituent; determined by the strength of the electron donation
biphenyl
If there is an activating group on one ring, the substitution reaction occurs on the same ring; if there is a passivating group, it occurs on the heterocyclic ring.
Properties of naphthalene
Electrophilic substitution reaction is dominated by C at α position
Special stability, easy to replace, difficult to add