Naphthenic hydrocarbon

Saturated hydrocarbon with alicyclic structure
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ring alkane (hu á n w á n t ī ng), containing alicyclic structure Saturated hydrocarbon There are monocyclic alicyclic and Fused ring Alicyclic. It contains one aliphatic ring and there is no substitution on the ring alkyl Naphthenic hydrocarbon with the general formula C n H 2n (n≧3)。 Cyclopentane cyclohexane And their alkyl substituted derivatives are petroleum products Cycloalkanes commonly found in. Polycyclic cycloalkanes exist at high boiling points Petroleum fraction Medium. Cycloalkanes have a high Calorific value freezing point Low, antiknock property is between normal hydrocarbon and isomeric hydrocarbon. chemical property Similar to alkanes. Among them, the properties of five carbon alicyclic ring and six carbon alicyclic ring are more stable.
Chinese name
Naphthenic hydrocarbon
Foreign name
naphthenes; cycloalkanes; cycloparaffins; naphthenic hydrocarbons
Meaning
Alicyclic Saturated hydrocarbon
Contains
There are monocyclic alicyclic and Fused ring Alicyclic ring
General formula of monocyclic molecule
C n H 2n (n≧3)

brief introduction

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Naphthenic hydrocarbon refers to molecular structure Containing one or more rings Saturated hydrocarbon Class compounds. The simplest alicyclic hydrocarbon is Cyclopropane
Alicyclic hydrocarbon is the main component of many important drugs.

nature

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one physical property : and alkane Similarly, naphthenic hydrocarbons are insoluble in water and soluble in benzene carbon tetrachloride chloroform Isopolar Organic solvent The boiling point, melting point and density of naphthenic hydrocarbon are all higher than those of carbon Atomic number The alkane content is high. [2]
two chemical property : (1) The chemical properties of cycloalkanes with large rings such as five membered rings and six membered rings are very similar to those of chain alkanes, which are similar to those of acids, bases, oxidants and reducing agent Generally, they do not react when exposed to light, heated at high temperature or heated at peroxide It can also happen if it exists Free radical Substitution reaction [1]
(2) Ternary and quaternary cycloalkanes are easy to occur Ring opening reaction , generating Open chain compound [1]

Classification and naming

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Naphthenic hydrocarbon
1. Classification of naphthenic hydrocarbon: (1) By carbon number: carbon atom When the number is 3~4, it is called small ring; When it is 5~6, it is called Ordinary ring When it is 7-12, it is called the middle ring; When it is greater than 12, it is called Macrocycle (2) According to the number of rings: if there is only one ring in the molecule, it is called a single ring; Two rings are called double rings; It is called multi ring if there are three or more rings. (3) According to the combination mode of rings: two rings share one carbon atom—— Screw ring Two rings share two carbon atoms—— Fused ring Two rings share more than two carbon atoms - bridge ring.
2. Name: (1) Single ring: add a "ring" before the name of the corresponding open chain hydrocarbon, if any functional group Make its position number the smallest or make the substituent have the lowest serial number as far as possible. (2) Polycyclic: In addition to adding the word "ring" before the name of the open chain hydrocarbon, it is also necessary to indicate the number of rings and the number of carbon atoms between the two bridgehead carbon atoms, which are separated by "·" and enclosed in square brackets.

stability

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one Angular tension two Torsional tension 3. Spatial steric resistance
have Aliphatic group Qualitative cyclic hydrocarbon , molecule contains closed carbon ring, but does not contain benzene ring
Alicyclic hydrocarbon The structural style of 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 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 hydrocarbons is to use ring characters to represent cyclohydrocarbons, use propane, butyl, and pentane to represent the number of carbon atoms in the ring, and use alkanes, alkenes, and alkynes to represent 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. The name of a spiro ring is similar to that of a bicyclic compound. It is called spiro alkane (or alkene) according to the total number of carbon atoms on the ring. Arabic numerals are used in square brackets to indicate the number of carbon atoms on two rings except for the shared carbon atoms. Write the number of carbon atoms on the small ring first. More complex compounds are commonly used by conventional names.
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.

Conformation of cycloalkanes

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1. Torsion boat type and half chair type.
(1) twist form
take Boat conformation The carbon of is twisted about 30 ° to become a boat twisting type:
cyclohexane Compared with the boat type, the torsion boat type conformation of the flagpole bond has lower hydrogen non bond tension; 7kJ lower than boat conformation· mol -1
(2) Half Chair conformation
Lift up the carbon C6 of the chair legs C2 , C4 and C5 form a plane to half chair conformation.
cyclohexane Half chair and Chair conformation Comparison: C2, C1, C6, C5, C4 have torsional tension. yes Angular tension 46kJ · mol more energy than chair -1
(3) Flip of ring:
When a Chair type If it turns into another chair conformation, it will go through two half chairs, two boat twisting and one boat.
In the chair conformation of cyclohexane, six carbon atom On two parallel planes respectively. C1, C3 and C5 are on the upper plane, and C2, C4 and C6 are on the lower plane. Cyclohexane ring has a triple Axis of symmetry Perpendicular to one of the planes.