Name: naming benzene derivatives with one group
Uploaded: 2023-04-30T10:30:47.000Z
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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

根据IUPAC命名法，单取代苯衍生物的命名是将取代基的名称作为前缀加在母体苯的名称之前。
国际纯粹与应用化学联合会（IUPAC）也接受了简单单取代苯衍生物的常见名称。例如，甲基苯称为甲苯，羟基苯称为苯酚。
苯及其烷基取代衍生物通常被称为芳烃。它们的命名取决于烷基的大小。
如果烷基含有六个或更少的碳原子，则该芳烃称为烷基取代苯。
相反，当烷基含有超过六个碳原子或包含其他官能团时，苯环被视为取代基，该芳烃称为苯基取代化合物。
苯基的缩写为Ph–，表示苯分子中的C6H5基团作为取代基，例如在2-苯基庚烷中。
同样，苄基（缩写为 Bn–）作为取代基时代表苯甲基，例如在氯化苄中。
芳基（简写为Ar–）是指从芳香环上移除一个氢原子后得到的、源自芳烃的取代基。

具有单一取代基的芳香族化合物的命名法

苯是最简单的芳香烃或芳烃。 简单单取代苯衍生物的 IUPAC 名称是通过将取代基名称作为前缀添加到母体苯而得出的。 例如，卤代苯，其中卤素可以是氟 (F)、氯 (Cl)、溴 (Br) 和碘 (I)。

 <img alt="Figure1" src="/files/ftp_upload/12449/12449_PT_Figure_1.svg" style="text-align: center; height: 100px;">

 芳香族化合物的命名还取决于苯环上连接的烷基的链长。 如果烷基链有六个或更少的碳，则该化合物被称为烷基取代的苯。 例如，丙苯，其中烷基具有三个碳。

 <img alt="Figure2" src="/files/ftp_upload/12449/12449_PT_Figure_2.svg" style="text-align: center; height: 125px;">

 然而，如果烷基链具有超过六个碳或含有其他优先官能团，则该化合物被称为苯基取代的衍生物。 从苯获得的取代基称为苯基（Ph-），而从甲苯获得的取代基称为苄基（Bn-）。 例如，1-苯基庚烷，其中烷基链有七个碳，

 <img alt="Figure3" src="/files/ftp_upload/12449/12449_PT_Figure_3.svg" style="text-align: center; height: 120px;">

 具有酮官能团的1-苯基-1-戊酮，

 <img alt="Figure4" src="/files/ftp_upload/12449/12449_PT_Figure_4.svg" style="text-align: center; height: 100px;">

 二苯醚，其中关键官能团是醚，

 <img alt="Figure5" src="/files/ftp_upload/12449/12449_PT_Figure_5.svg" style="text-align: center; height: 80px;">

 和由甲苯衍生的苄基溴。

 <img alt="Figure6" src="/files/ftp_upload/12449/12449_PT_Figure_6.svg" style="text-align: center; height: 100px;">

 一般来说，由芳烃失去氢而衍生的取代基称为芳基。 一些简单的单取代苯衍生物已获得 IUPAC 命名法所接受的通用名称。 例如，乙烯基苯是苯乙烯，异丙苯是枯烯。 苯甲醛和苯甲酸是其他例子。

 <img alt="Figure7" src="/files/ftp_upload/12449/12449_PT_Figure_7.svg" style="text-align: center; height: 120px;">

苯是最简单的芳香烃或芳烃。简单单取代苯衍生物的IUPAC名称是通过在……的基础上添加……而得到的。

Education

教育

JoVE Core

Organic Chemistry

有机化学

Unit 1

第一单元

Aromatic Compounds

芳香族化合物

KEY TERMS AND CONCEPTS

关键术语与概念

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

organic chemistry

JoVE Core 有机化学（Organic Chemistry）使用简明易懂的动画视频课程解释立体化学、反应和机制的基本概念。 此外，科学家在行动视频展示了相关概念在当今世界各地实验室进行的经典和原创研究实验中的应用。

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Naming Benzene Derivatives with One Group

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