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MindMap Gallery Classification and naming of organic matter (Part 1)

Classification and naming of organic matter (Part 1)

University medical organic chemistry mainly introduces saturated hydrocarbons, unsaturated hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, alcohols, phenols, ethers, etc. in detail to help you become familiar with the key points of knowledge and enhance your memory. Students in need can save it.

Edited at 2024-12-15 22:15:06

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Classification and naming of organic matter (Part 1)

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Classification and naming of organic matter (Part 1)

Saturated hydrocarbons

Alkanes

systematic nomenclature

IUPAC naming principles

The carbon chain is the longest, the branches are nearest, and the total number is smallest.

Br>Cl>Cycle>Ethyl>Methyl>Propyl (order)

The branch chain with the higher alphabetical order (order) is written first. When two different branches are in the same order from both ends, the branch chain with the higher order is listed first.

eg: 2,3,5-trimethyl-4-propylheptane

cycloalkanes

Monocyclic alkanes

cycloalkane

The C number attached to the lowest-order substituent is 1, and the position numbers of other substituents are as small as possible.

When a more complex C chain is connected to a simple ring, or several alicyclic hydrocarbons are connected to the same C chain, the ring can be used as a substituent. eg: 3-cyclopropyl-5-methylheptane

Polycycloalkanes

Spirocyclic hydrocarbons

According to the total number of carbon atoms in the ring, it is called: spiro [ ] a certain alkane. In [ ], indicate the number of carbon atoms in each ring except spiro atoms. Arrange from small to large, separated by dots

Numbering: Start from the small ring → spiro atom → macrocycle, and make the substituent number as small as possible.

eg: 5-methylspiro[2.4]heptane

Bridged cyclic hydrocarbons

According to the total number of carbons in the ring, it is called a bicyclic [ ] alkane. [ ] indicates the carbons in each bridge except the bridgehead carbon. Atomic numbers, arranged from largest to smallest, separated by dots

Numbering: start from one bridgehead carbon → macrocycle → another bridgehead carbon → small ring, try to make the substituents as many as possible The smallest number.

eg: 8,8-dimethylbicyclo[3.2.1]octane

unsaturated hydrocarbons

ene

common nomenclature

Ethylene, propylene, isobutylene

systematic nomenclature

The longest carbon chain is selected as the main chain; numbering starts from the end closest to the unsaturated bond; the cycloolefin is called a cycloolefin depending on the size of the ring.

eg:3-cyclohexyl-2-methylprop-1-ene

alkenyl

CH3CH2=CH- 1-propenyl (propenyl)

CH2=CHCH2- 2-propenyl(allyl)

If the atoms or groups connected to two double bonded carbon atoms are the same as each other

cis-trans isomerism

Sequence rules

(1) Atoms with a large atomic number are given priority over atoms with a small atomic number. For isotopes, those with higher mass numbers are preferred. Such as: -I>-Br>-Cl>-SH>-NH2>-CH3>-D>-H

(2) If the atoms connected to the main chain are the same, the atoms connected to the atom are compared successively. For example: -CH3 and -CH2CH3 are C.H.H.H and C.C.H.H, and the ethyl group has priority.

(3) If the atoms in the substituent are connected by double bonds or triple bonds, the atoms are regarded as connected twice or three times.

On the same side is called the cis configuration, On the opposite side is the trans configuration.

In compounds containing multiple double bonds, when the number of the main chain is selected, one of the cis double bonds should be selected. end starts. eg: cis, trans-hept-2,5-diene

If the four atoms or groups connected to two double-bonded carbon atoms are not the same

Z/E configuration notation

Compare the priorities of the two groups on each double bond carbon according to the order rules. If the priority group (larger group) is on the same side of the double bond, it is the Z (Zusammen, Z) configuration. The priority group is on the double bond. The opposite side of the bond is E (Entgegen, E) configuration.

Alkyne

When a compound contains both a double bond and a triple bond, and the double bond and triple bond are at different positions from the end of the carbon chain, the bond and triple bond should be given the lowest possible number.

If the double bond and triple bond are at the same distance from the end of the carbon chain, they are numbered in the order of alkenes first and then alkynes.

Aromatic hydrocarbons

monosubstituted benzene

Benzene as parent

Toluene, cumene, bromobenzene, nitrobenzene

Benzene as a group

Phenyl: styrene, 2-methyl-4-phenylpentane Benzyl: benzyl alcohol, benzyl chloride

polysubstituted benzene

Parent selection priority: -SO3H>-COOH>-OH>-NH2>-R>-NO2>-X ortho 0, between m, pair p, both

Halogenated hydrocarbons

IUPAC naming principles

The carbon chain is the longest, the branches are nearest, and the total number is smallest.

Br>Cl>Cycle>Ethyl>Methyl>Propyl (order)

The branch chain with the higher alphabetical order (order) is written first. When two different branches are in the same order from both ends, the branch chain with the higher order is listed first.

eg: 2,3,5-trimethyl-4-propylheptane

eg: 3-chloro-1-methylcyclohexene

Alcohol, phenol, ether

alcohol

Choose the longest carbon chain containing -OH as the main chain, number it from the carbon atom near the -OH end, and call it "an alcohol" according to the number of carbon atoms contained in the main chain, and add the word "an alcohol" or "alcohol" The position of the hydroxyl group is indicated above.

phenol

When naming phenol, phenol can be used as the parent, or aromatic hydrocarbons can be used as the parent. If the molecule contains only phenolic hydroxyl groups, phenol is used as the parent; if the molecule contains multiple hydroxyl groups and hydrocarbon groups, aromatic hydrocarbons are used as the parent and phenolic hydroxyl groups are used as substituents.

p-Chlorophenol, benzene-1,3-diphenol, 2,3-dihydroxytoluene

ether

common nomenclature

Just add the word "ether" after the two hydrocarbon names. eg: diethyl ether, methyl tert-butyl ether

systematic nomenclature

Choose a longer hydrocarbon group as the parent, and use a hydrocarbon group with a smaller number of carbon atoms and an oxygen atom called an alkoxy group as a substituent. When there is an unsaturated hydrocarbon group, the hydrocarbon group with a greater degree of unsaturation is used as the parent. eg: 2-methyl-1-methoxypent-1-ene