Alicyclic hydrocarbon

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alicyclic hydrocarbon , with Aliphatic group Qualitative cyclic hydrocarbon The molecule contains a closed carbon ring.

Chinese name: Alicyclic hydrocarbon
Foreign name: alicyclic hydrocarbon

Features: have Aliphatic group Qualitative cyclic hydrocarbon
Nature: Progressiveness Substitution reaction and Ring opening reaction etc.

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Structure introduction

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Common structural formula of alicyclic hydrocarbon polygon Indicates that each vertex of the polygon represents one carbon atom And deductions Substituent After that, it is necessary to keep the carbon atom at 4 valence hydrogen atom 。

Alicyclic hydrocarbon can also contain more than two carbon rings, which can be connected in many ways: two rings in the molecule can share one carbon atom, and this system is called Screw ring ； The two carbon atoms on the ring can be connected by carbon bridge to form a double ring or multi ring system, called bridge ring; Several rings can also be connected with each other to form a cage structure.

The designation of monocyclic hydrocarbon is to use ring characters to represent cyclohydrocarbon, and use C, D, E, etc. to represent the number of carbon atoms in the ring Alkane , alkene, alkyne, etc. indicate that only Single bond Or double bond Triple bond , substituent expression method and Alkane Same. Bicyclic hydrocarbon is called bicyclic alkane (or alkene) according to the total number of carbon atoms in the ring square brackets Internal use Arabic numerals Indicates the number of carbon atoms on each carbon bridge connecting the carbon atoms at the bridgehead. Write first Macrocycle Carbon of Atomic number 。 If the two bridgehead carbon atoms are directly connected, the number of carbon atoms on the bridge is 0. Arabic numerals are separated by dots. Screw ring The name of is similar to that of bicyclic compounds. According to the total number of carbon atoms on the ring, it is called spiro alkane (or alkene). In square brackets, use Arabic numerals to indicate the number of carbon atoms on two rings, except for sharing carbon atoms. Write the number of carbon atoms on the small ring first. Common habits of more complex compounds Nomenclature 。

At room temperature and atmospheric pressure, Cyclopropane and Cyclobutane Is gas, Cyclopentane To ring Undecane Is liquid, Cyclododecane The above is solid. Naphthene Melting point, boiling point and relative density Both contain the same number carbon atom High linear alkanes. Cyclopentane cyclohexane And alkyl Substitutes exist in certain oils. Cyclohexane is an important chemical raw material.

relationship

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Organic chemistry In general, organics are divided into three categories: 1 Open chain compound , in molecule carbon atom Connected into a chain, also known as“ Aliphatic compounds ”； two Carbocyclic compound , the carbon atoms in the molecule are connected into a ring, including the alicyclic group and Aromatic compound ； three Heterocyclic compound , that is, the molecule contains other atoms (such as O, N, S, etc.) Cyclic compound 。 Corresponding aliphatic chain hydrocarbon and alicyclic hydrocarbon Aromatic hydrocarbon Outer ring hydrocarbon.

chemical property

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Alicyclic chemical property Although corresponding to Aliphatic hydrocarbon Similar, but it has a ring structure, and the ring has size, so it also has the characteristics of a ring structure.

Naphthenic hydrocarbon Nature of

one Substitution reaction : Induced by light and heat, Naphthenic hydrocarbon And alkane Same can happen Free radical Substitution reaction. For example Halogenation reaction , generate the corresponding Halogenated substance 。

two Ring opening reaction —— Addition reaction : The middle and small rings of cycloalkanes are different from alkanes, showing a special chemical property ——It is easy to open the ring and generate addition reaction.

(1) Hydrogenation: in catalyst platinum, palladium or Raney nickel Under the action of, Cyclopropane and Cyclobutane Open with hydrogen Cycloaddition reaction 。 For example, cyclopropane undergoes ring opening addition reaction at nickel and 80 ℃ to generate positive propane 。 (Cyclopropane is easy to be hydrogenated, while cyclobutane can only be hydrogenated at a higher temperature Cyclopentane and cyclohexane Hydrogenation must be possible under more intense conditions)

(2) Plus halogen ： Small cyclic alkane It is also opened with halogen Cycloaddition reaction For example, cyclopropane also occurs with bromine at room temperature Ring opening reaction To produce 1,3-dibromopropane.

(3) Plus Hydrogen halide : Cyclopropane can also be used with Hydrogen bromide Ring opening addition reaction occurs to generate corresponding Haloalkane (It should be noted that when the alkyl derivatives of cyclopropane undergo ring opening reaction with hydrogen halide, the ring rupture occurs in the two with the most and the least hydrogen carbon atom And follow Markovian addition rule)

In short, the four membered ring is not as easy to open as the three membered ring, and does not react with halogen and hydrogen halide at room temperature, Cyclopentane and cyclohexane So it is.

three oxidation reaction : Cyclopentane does not react with ordinary oxidants at room temperature. But when heating Strong oxidant Or in the presence of catalyst Air oxidation , it can be oxidized into various Oxidation product 。

Cycloolefin And ring Diene Nature of

Cycloolefin

（1） Addition reaction Cycloolefins have similar properties olefin , double bond is prone to hydrogenation, halogenation Hydrogen halide And react with sulfuric acid.

（2） oxidation reaction The double bond of cycloolefin is also easily potassium permanganate Or ozone oxidation Oxidation product

ring Diene

Conjugated cyclodienes and some compounds containing Unsaturated compound happen Diene synthesis reaction

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