Name: naming benzene derivatives with one group
Uploaded: 2023-04-30T10:30:47.000Z
Duration: 1 min 23 s
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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-a-single-substituent

Nomenclature of Aromatic Compounds with a Single Substituent

IUPAC 명명법에 따르면, monosubstituted benzene derivatives는 부모 벤젠에 치환기의 이름을 접두사로 붙여서 명명됩니다.
IUPAC은 또한 단순한 일치환 벤젠 유도체에 대한 일반적인 이름을 허용했습니다. 예를 들어, 메틸벤젠의 경우 톨루엔, 하이드록시벤젠의 경우 페놀이 있습니다.
벤젠 및 그 알킬 치환 유도체는 종종 아렌(arene)이라고 합니다. 그들은 알킬 그룹의 크기에 따라 명명됩니다.
알킬기가 6개 이하의 탄소를 가지고 있는 경우, 아렌은 알킬 치환된 벤젠이라고 합니다.
반대로, 알킬기가 6개 이상의 탄소를 갖거나 다른 작용기로 구성된 경우, 벤젠 고리는 치환체로 취급됩니다. 그리고 arene은 페닐 치환 화합물이라고합니다.
Ph–로 약칭되는 페닐이라는 이름은 2-페닐헵탄과 같은 치환기로 벤젠의 C6H5 그룹을 나타냅니다.
유사하게, Bn–으로 약칭되는 벤질은 페닐메틸기를 염화벤질과 같은 치환기로 나타냅니다.
Ar–로 약칭되는 Aryl은 방향족 고리에서 수소 원자를 제거한 후 아렌에서 파생된 치환기입니다.

단일 치환기를 갖는 방향족 화합물의 명명법

벤젠은 가장 단순한 방향족 탄화수소 또는 아렌입니다. 단순 단일 치환 벤젠 유도체의 IUPAC 이름은 모 벤젠에 접두사로 치환체 이름을 추가하여 파생됩니다. 예를 들어 할로벤젠은 할로겐이 플루오로(F), 클로로(Cl), 브로모(Br), 요오도(I)일 수 있습니다.

<img alt="Figure1" src="/files/ftp_upload/12449/12449_PT_Figure_1.svg" style="text-align: center; height: 100px;">

방향족 화합물의 이름은 벤젠 고리에 부착된 알킬기의 사슬 길이에 따라 달라집니다. 알킬 사슬의 탄소 수가 6개 이하인 경우 해당 화합물은 알킬 치환 벤젠으로 명명됩니다. 예를 들어, 알킬 그룹에 3개의 탄소가 있는 프로필벤젠이 있습니다.

<img alt="Figure2" src="/files/ftp_upload/12449/12449_PT_Figure_2.svg" style="text-align: center; height: 125px;">

그러나 알킬 사슬에 탄소 수가 6개 이상이거나 다른 우선적인 작용기를 포함하는 경우 해당 화합물은 페닐 치환 유도체로 명명됩니다. 벤젠에서 얻은 치환기를 페닐(Ph-)이라 하고, 톨루엔에서 얻은 치환기를 벤질(Bn-)기라고 합니다. 예를 들어, 알킬 사슬에 7개의 탄소가 있는 1-페닐헵탄은

<img alt="Figure3" src="/files/ftp_upload/12449/12449_PT_Figure_3.svg" style="text-align: center; height: 120px;">

케톤 작용기를 갖는 1-페닐-1-펜타논,

<img alt="Figure4" src="/files/ftp_upload/12449/12449_PT_Figure_4.svg" style="text-align: center; height: 100px;">

주요 작용기가 에테르인 디페닐 에테르,

<img alt="Figure5" src="/files/ftp_upload/12449/12449_PT_Figure_5.svg" style="text-align: center; height: 80px;">

및 톨루엔으로부터 유래된 벤질브로마이드.

<img alt="Figure6" src="/files/ftp_upload/12449/12449_PT_Figure_6.svg" style="text-align: center; height: 100px;">

일반적으로 아렌에서 수소를 잃어 파생된 치환기를 아릴이라고 합니다. 단순 일치환 벤젠 유도체 중 일부는 IUPAC 명명법에 의해 허용되는 일반 이름을 얻었습니다. 예를 들어 비닐벤젠은 스티렌이고 이소프로필벤젠은 큐멘입니다. 벤즈알데히드와 벤조산이 또 다른 예입니다.

<img alt="Figure7" src="/files/ftp_upload/12449/12449_PT_Figure_7.svg" style="text-align: center; height: 120px;">

벤젠은 가장 단순한 방향족 탄화수소 또는 아렌입니다. 간단한 monosubstituted 벤젠 유래물을 위한 IUPAC 이름은 다음을 추가해서 파생됩니다 ...

Education

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JoVE Core

Organic Chemistry

유기 화학

Unit 1

제1단원

Aromatic Compounds

방향족 화합물

KEY TERMS AND CONCEPTS

주요 용어 및 개념

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 has six or fewer carbons, the compound is named as an alkyl-substituted benzene. Propylbenzene is one example, and its alkyl group has three carbons. If the alkyl chain has more than six carbons, or if another preferred functional group is present, the compound is named as a phenyl-substituted derivative.

The benzene-derived substituent is called phenyl, written as Ph-. The group derived from toluene is called benzyl, written as Bn-. Examples include 1-phenylheptane, 1-phenyl-1-pentanone, diphenyl ether, and benzyl bromide. In general, substituents formed from arenes by loss of hydrogen are called aryl groups. Some simple monosubstituted benzene derivatives also have common names accepted by IUPAC, including styrene for vinylbenzene, cumene for isopropylbenzene, benzaldehyde, and benzoic acid.

Naming Benzene Derivatives with One Group

naming-benzene-derivatives-with-one-group

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

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

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

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,...

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 benzene derivatives with one substituent are named, including halobenzene, alkylbenzene, phenyl, benzyl, and common IUPAC names.

Naming Benzene Derivatives with One Group | JoVE K12

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Naming Benzene Derivatives with One Group

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