Name: naming benzene rings with multiple groups
Uploaded: 2025-05-22T09:05:43.000Z
Duration: 1 min 11 s
Channel: JoVE

K12 Standards

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NC K-12 Science Standard Course of Study

9-12

Physical Science

Matter and its Interactions

PS.PSc.2.2

nomenclature-of-aromatic-compounds-with-multiple-substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

여러 치환체를 가진 방향족 화합물의 IUPAC 명명법은 치환기의 수와 위치에 따라 다릅니다.
치환된 벤젠 유도체의 이름을 지정하기 위해 치환의 위치는 각각 o, m 및 p로 축약된 접두사 ortho, meta 및 para를 사용하거나 ortho의 경우 1,2-, meta의 경우 1,3-, para의 경우 1,4-와 같은 숫자를 사용하여 표시됩니다. 
두 치환이 다른 경우 번호가 매겨지고 알파벳순으로 나열됩니다.
치환기 중 하나가 화합물에 공통 이름을 부여하면 화합물은 해당 부모 분자의 유도체로 명명됩니다.
두 개 이상의 치환체를 가진 폴리치환된 벤젠 유도체의 이름을 지정하기 위해 숫자는 치환체의 위치를 나타내는 데 사용됩니다.
치환에는 가능한 가장 낮은 숫자가 주어지며 알파벳 순으로 나열됩니다.
어떠한 치환기라도 일반적인 이름을 부여하면, 그것은 locant 1로 지정되고, 화합물은 그 부모 분자의 유도체로서 명명된다.

다중 치환기를 갖는 방향족 화합물의 명명법

벤젠 고리에 두 개의 그룹이 부착된 이치환된 벤젠 유도체의 경우 세 가지 구성 이성질체가 가능합니다. 예를 들어, 두 번째 메틸 그룹이 두 번째, 세 번째 또는 네 번째 탄소에서 치환될 수 있는 자일렌이라고도 불리는 디메틸 벤젠을 생각해 보세요. 치환기의 상대적 위치는 접두사 오르토(ortho), 메타(meta), 파라(para)로 표시됩니다. 이러한 용어는 단일 문자로 표시될 수도 있습니다. 오르토는 'o', 메타는 'm', 파라는 'p'입니다. 숫자는 오르토의 경우 1,2-, 메타의 경우 1,3-, 파라의 경우 1.4-와 같이 연결된 그룹의 상대적 위치를 나타내는 데에도 사용할 수 있습니다. 예를 들어, 디메틸 벤젠에 가능한 세 가지 다른 구조는 아래와 같습니다.

<img alt="Figure1" src="/files/ftp_upload/12865/12865_PT_Figure_1.svg" style="text-align: center; height: 185px;">

두 치환기가 다른 경우 벤젠 앞에 접두사로 번호를 매기고 알파벳 순서로 나열됩니다.

<img alt="Figure2" src="/files/ftp_upload/12865/12865_PT_Figure_2.svg" style="text-align: center; height: 125px;">

치환기 중 하나가 일반 이름의 일부인 경우 해당 화합물은 해당 모 화합물의 파생어로 명명됩니다.

<img alt="Figure3" src="/files/ftp_upload/12865/12865_PT_Figure_3.svg" style="text-align: center; height: 140px;">

다중 치환된 벤젠 유도체는 벤젠 고리에 3개 이상의 치환기가 부착되어 있습니다. 이름을 지정하기 위해 숫자는 연결된 그룹의 상대적 위치를 나타내는 데 사용되며 아래와 같이 각 그룹에는 가능한 가장 낮은 번호가 할당됩니다.

<img alt="Figure4" src="/files/ftp_upload/12865/12865_PT_Figure_4.svg" style="text-align: center; height: 135px;">

마지막으로, 치환기는 아래와 같이 벤젠의 접두사로 알파벳순으로 정렬됩니다.

<img alt="Figure5" src="/files/ftp_upload/12865/12865_PT_Figure_5.svg" style="text-align: center; height: 150px;">

치환기 중 하나가 일반 이름을 부여하면 위치 1이 부여되고 분자는 아래와 같이 해당 모 화합물의 파생물로 명명됩니다.

<img alt="Figure6" src="/files/ftp_upload/12865/12865_PT_Figure_6.svg" style="text-align: center; height: 125px;">

벤젠 고리에 둘 이상의 치환체가 존재하는 경우 IUPAC 명명법은 존재하는 치환기의 수에 따라 다릅니다.
대체된 ...

Education

교육

JoVE Core

Organic Chemistry

유기 화학

Unit 1

제1단원

Aromatic Compounds

방향족 화합물

KEY TERMS AND CONCEPTS

주요 용어 및 개념

naming benzene rings with multiple groups

Naming benzene rings with multiple groups depends on how many substituents are attached. For benzene derivatives with two groups, three constitutional isomers are possible. The position of each group is described with IUPAC naming rules.

For disubstituted benzene compounds, the relative positions can be shown with ortho, meta, and para. These terms are also written as o, m, and p. They can also be written with numbers, such as 1,2- for ortho, 1,3- for meta, and 1,4- for para. Dimethyl benzene, also called xylene, is a common example of this pattern because the second methyl group can attach at the second, third, or fourth carbon.

When the two substituents are different, they are numbered and listed in alphabetical order before benzene. If one substituent belongs to a common name, the compound is named as a derivative of that parent compound. For polysubstituted benzene derivatives, which have three or more substituents, numbers show the positions of the attached groups, and the lowest possible numbers are assigned to each group. The substituents are then listed in alphabetical order, and if a common name is present, it gets locant 1 and the molecule is named as a derivative of that parent compound.

Naming Benzene Rings with Multiple Groups

naming-benzene-rings-with-multiple-groups

aromatic compounds: overview

Aromatic Compounds in Plants and Fuels

Aromatic compounds are linked to both pleasant smells and important chemical structures. The word aromatic first came from fragrant natural sources such as fresh flowers and spices. Early organic chemists isolated benzene derivatives from oils of plants, including vanillin from vanilla, methyl salicylate from wintergreen, and cinnamaldehyde from cinnamon. The history of benzene also helped shape the idea of aromatic compounds. In 1825, Faraday isolated benzene from compressed illuminating gas,...

nomenclature of aromatic compounds with a single substituent

nomenclature-of-aromatic-compounds-with-a-single-substituent

Naming Benzene Derivatives with One Group

Benzene derivatives with one substituent are named by attaching the substituent name to benzene. Benzene is the simplest aromatic hydrocarbon, also called an arene. For simple monosubstituted benzene compounds, IUPAC naming uses the group name as a prefix. Halogen-substituted benzene compounds follow this pattern. The halogen prefix can be fluoro, chloro, bromo, or iodo. When an alkyl group is attached to the benzene ring, the name depends on the chain length of that group. If the alkyl chain...

nomenclature of aromatic compounds with multiple substituents

Naming benzene rings with multiple groups depends on how many substituents are attached. For benzene derivatives with two groups, three constitutional isomers are possible. The position of each group is described with IUPAC naming rules. For disubstituted benzene compounds, the relative positions can be shown with ortho, meta, and para. These terms are also written as o, m, and p. They can also be written with numbers, such as 1,2- for ortho, 1,3- for meta, and 1,4- for para. Dimethyl benzene,...

structure of benzene: kekul&eacute; model

Kekule’s Benzene Model and Its Limits

Kekule’s benzene model describes benzene as a six-carbon ring with alternating pi bonds. August Kekule proposed this structure in 1865 from the formula C6H6, the idea that all benzene hydrogens are equivalent, and the rule that each carbon has four bonds because of tetravalency. In this model, each carbon is attached to one hydrogen atom. It also predicts two isomers for 1,2-disubstituted benzene derivatives. In one form, the substituted carbons are linked by a double bond, and in the other...

structure of benzene: molecular orbital model

structure-of-benzene-molecular-orbital-model

Benzene π Orbitals and Electron Delocalization

Benzene has a planar ring structure with delocalized π electrons. Its six carbon atoms form a regular hexagon, and each carbon is sp2 hybridized. The C–C–C and H–C–C bond angles are 120°, which matches the flat shape of the ring. Each carbon is bonded to three other atoms. The C–H bond length is 109 pm, and the C–C bond length is 139 pm. That C–C distance is midway between the single bond length of sp3 hybridized carbons, 154 pm, and the sp2 value, 133 pm. Beneath and above the ring plane,...

criteria for aromaticity and the h&uuml;ckel 4n + 2 rule

criteria-for-aromaticity-and-the-hckel-4n-2-rule

H&uuml;ckel Rule and Aromatic Ring Criteria

Aromatic rings follow H&amp;uuml;ckel’s rule, also called the 4n + 2 rule. This rule helps identify which unsaturated cyclic compounds are aromatic and why some ring systems are unstable instead. Benzene is the classic example, while cyclobutadiene and cyclooctatetraene show different behavior and are not aromatic. Eric H&amp;uuml;ckel, a German chemical physicist, first described the structural features needed for aromaticity. An aromatic compound must be cyclic, planar, and continuously...

h&uuml;ckel's rule diagram of &pi; mos: frost circle

Frost Circle for Pi Orbital Energies

The Frost circle is a graphical method for showing the relative energies of pi molecular orbitals in planar, fully conjugated, monocyclic compounds. It is also called the inscribed polygon method. A. A. Frost and Boris Musulin first described this method in 1953. To build a Frost circle, draw a polygon with the same number of edges as the number of carbons in the cyclic system. Place one vertex pointing downward. Then draw a circle around the polygon so that every vertex touches the circle.

frost circles for different conjugated systems

frost-circles-for-different-conjugated-systems

Using Frost Circles to Test Aromaticity

Frost circles help test whether a cyclic compound is aromatic by using the inscribed polygon method and Hückel’s 4n + 2 rule. A compound is stable and aromatic when every bonding molecular orbital (MO) is completely filled with a pair of electrons. If electrons occupy non-bonding or antibonding orbitals, the compound is unstable and not aromatic. Frost circle diagrams for cycloalkenes with 4 to 8 carbons show a clear pattern. The number of bonding MOs is always odd. The electrons needed to...

aromatic hydrocarbon anions: structural overview

aromatic-hydrocarbon-anions-structural-overview

Cyclopentadienyl Anion and Aromaticity

Cyclopentadiene is a neutral hydrocarbon that is not aromatic. It contains an odd number of carbon atoms and one CH2 group in the ring. With only 4 pi electrons, it does not follow the 4n + 2 pi electron rule. The CH2 carbon is sp3 hybridized, so it has no vacant p orbital to keep p orbitals overlapped around the ring. That break in overlap stops pi electrons from spreading across the entire ring. As a result, cyclopentadiene does not meet the usual aromaticity criteria. If one hydrogen is...

aromatic hydrocarbon cations: structural overview

aromatic-hydrocarbon-cations-structural-overview

Cycloheptatrienyl Cation and Aromaticity

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon with seven carbon atoms. One carbon in the ring is sp3 hybridized, which breaks the continuous overlap of p orbitals. Even though the ring has three double bonds and 6 π electrons, cycloheptatriene is not aromatic because the p orbitals do not form one uninterrupted loop. Removing one hydrogen from the CH2 group changes the ring. If that hydrogen is removed with both, one, or no electrons, the products are the cycloheptatrienyl...

five-membered heterocyclic aromatic compounds: overview

five-membered-heterocyclic-aromatic-compounds-overview

Five-Membered Aromatic Rings with Heteroatoms

Five-membered aromatic rings with heteroatoms are cyclic compounds that contain one or more atoms other than carbon in the ring. They are aromatic and can have either five or six atoms in the ring. Common examples include pyrrole, furan, thiophene, and imidazole. These rings differ by the heteroatom present. Pyrrole has one nitrogen atom with one lone pair of electrons. Furan has one oxygen atom, and thiophene has one sulfur atom. Both furan and thiophene have two lone pairs of electrons.

nmr spectroscopy of aromatic compounds

Aromatic Ring Shifts in NMR Spectra

Aromatic ring shifts in NMR spectra help identify aromatic compounds using proton NMR and carbon-13 NMR. Aromatic hydrogens are often strongly deshielded by the aromatic ring current, so they usually appear in the 6.5–8.0 ppm range in proton NMR. In benzene, the hydrogens directly bonded to the ring absorb at 7.3 ppm. Larger aromatic rings can place hydrogens outside the usual range. In [18]annulene, the 12 outer hydrogens are highly deshielded by the ring current and absorb downfield at 9.3...

key terms and concepts

Learn how to name benzene rings with two or more substituents using ortho, meta, para, numbered positions, alphabetical order, and common parent names.

Naming Benzene Rings with Multiple Groups | JoVE K12

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Naming Benzene Rings with Multiple Groups

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