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

K12 Standards

north-carolina-k-12-science-standard-course-of-study

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

Secondo la nomenclatura IUPAC, i derivati del benzene monosostituiti sono denominati anteponendo il nome del sostituente al benzene genitore.
La IUPAC ha anche accettato nomi comuni per semplici derivati del benzene monosostituiti. Ad esempio, il toluene per il metilbenzene e il fenolo per l'idrossibenzene.
Il benzene e i suoi derivati alchil-sostituiti sono spesso indicati come areni. Prendono il nome in base alle dimensioni del gruppo alchilico.
Se il gruppo alchilico ha sei o meno atomi di carbonio, allora l'arene è definito benzene alchil-sostituito.
Al contrario, quando il gruppo alchilico ha più di sei atomi di carbonio o è costituito da altri gruppi funzionali, l'anello benzenico viene trattato come un sostituente. E l'arene è definito un composto fenil-sostituito.
Il nome fenile, abbreviato in Ph–, rappresenta il gruppo C6H5 del benzene come sostituente, come nel 2-fenileptano.
Allo stesso modo, il benzile, abbreviato in Bn–, rappresenta il gruppo fenilmetilico come sostituente, come nel cloruro di benzile.
L'aril, abbreviato in Ar–, è il sostituente derivato da un arene dopo la rimozione di un atomo di idrogeno dall'anello aromatico.

nomenclatura dei composti aromatici con un sostituente singolo

Il benzene è l'idrocarburo aromatico o arene più semplice. I nomi IUPAC per semplici derivati del benzene monosostituito vengono derivati aggiungendo il nome del sostituente come prefisso al benzene genitore. Ad esempio, alobenzene, dove l'alogeno potrebbe essere fluoro (F), cloro (Cl), bromo (Br) e iodio (I).

<img alt="Figure1" src="/files/ftp_upload/12449/12449_PT_Figure_1.svg" style="text-align: center; height: 100px;">

La denominazione dei composti aromatici dipende anche dalla lunghezza della catena del gruppo alchilico attaccato all'anello benzenico. Se la catena alchilica ha sei o meno atomi di carbonio, il composto è chiamato benzene alchil-sostituito. Ad esempio, il propilbenzene, dove il gruppo alchilico ha tre atomi di carbonio.

<img alt="Figure2" src="/files/ftp_upload/12449/12449_PT_Figure_2.svg" style="text-align: center; height: 125px;">

Tuttavia, se la catena alchilica ha più di sei atomi di carbonio o contiene altri gruppi funzionali preferenziali, il composto viene denominato derivato fenil-sostituito. Il sostituente ottenuto dal benzene è chiamato fenile (Ph-), mentre quello derivato dal toluene è chiamato gruppo benzilico (Bn-). Ad esempio, 1-fenileptano, dove la catena alchilica ha sette atomi di carbonio,

<img alt="Figure3" src="/files/ftp_upload/12449/12449_PT_Figure_3.svg" style="text-align: center; height: 120px;">

1-fenil-1-pentanone con un gruppo funzionale chetone,

<img alt="Figure4" src="/files/ftp_upload/12449/12449_PT_Figure_4.svg" style="text-align: center; height: 100px;">

etere difenilico, dove il gruppo funzionale chiave è l'etere,

<img alt="Figure5" src="/files/ftp_upload/12449/12449_PT_Figure_5.svg" style="text-align: center; height: 80px;">

e bromuro di benzile derivato dal toluene.

<img alt="Figure6" src="/files/ftp_upload/12449/12449_PT_Figure_6.svg" style="text-align: center; height: 100px;">

In generale, i sostituenti derivati dagli areni per perdita di idrogeno sono chiamati arili. Alcuni dei derivati semplici del benzene monosostituito hanno acquisito nomi comuni accettati dalla nomenclatura IUPAC. Ad esempio, il vinilbenzene è lo stirene e l'isopropilbenzene è il cumene. Altri esempi sono la benzaldeide e l'acido benzoico.

<img alt="Figure7" src="/files/ftp_upload/12449/12449_PT_Figure_7.svg" style="text-align: center; height: 120px;">

Nomenclatura dei Composti Aromatici con un sostituente singolo

Il benzene è l'idrocarburo aromatico più semplice o arene. I nomi IUPAC per semplici derivati del benzene monosostituito sono derivati aggiungendo il ...

Education

Didattica

JoVE Core

Organic Chemistry

Chimica Organica

Unit 1

Unità 1

Aromatic Compounds

Composti aromatici

KEY TERMS AND CONCEPTS

TERMINI E CONCETTI CHIAVE

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 Organic Chemistry spiega i concetti di base della stereochimica, delle reazioni e dei meccanismi usando video-lezioni concise e facili da capire. Inoltre, i video scientist-in-action dimostrano l'applicazione di tali concetti in esperimenti di ricerca classici e originali eseguiti al giorno d'oggi nei laboratori in tutto il mondo.

Classifying Matter by State

Chemistry is the study of matter and the changes it undergoes. Matter is anything that has mass and occupies space. Matter is all around us; the air, ...

Classifying Matter by Composition

Matter: Pure Substances and Mixtures
According to its composition, the matter can be classified into two broad categories &mdash; pure substances and ...

Elements: Chemical Symbols and Isotopes

A chemical symbol is an abbreviation used to indicate an element or an atom of an element. For example, the symbol for mercury is Hg. The same symbol is ...

Molecules and Compounds

Atoms and Molecules

Everything in the universe is made up of matter, and matter is composed of a combination of elements. An atom is the smallest unit of ...

Solution Formation

There is no one solvent that can dissolve every type of solute. Some substances that readily dissolve in a certain solvent might be insoluble in a ...

Colloids

Children at play often make suspensions such as mixtures of mud and water, flour and water, or a suspension of solid pigments in water known as tempera ...

Construct an explanation to classify matter as a pure substance or mixture; homogeneous or heterogeneous; element or compound; solution, colloid or suspension.

PS.PSc.1.1

Phase Transitions

Whether solid, liquid, or gas, a substance&#39;s state depends on the order and arrangement of its particles (atoms, molecules, or ions). Particles in the ...

phase-transitions-vaporization-and-condensation

Phase Transitions: Vaporization and Condensation

The physical form of a substance changes on changing its temperature. For example, raising the temperature of a liquid causes the liquid to vaporize ...

Vapor Pressure

When a liquid vaporizes in a closed container, gas molecules cannot escape. As these gas phase molecules move randomly about, they will occasionally ...

Clausius-Clapeyron Equation

The equilibrium between a liquid and its vapor depends on the temperature of the system; a rise in temperature causes a corresponding rise in the vapor ...

Phase Transitions: Melting and Freezing

Heating a crystalline solid increases the average energy of its atoms, molecules, or ions, and the solid gets hotter. At some point, the added energy ...

phase-transitions-sublimation-and-deposition

Phase Transitions: Sublimation and Deposition

Some solids can transition directly into the gaseous state, bypassing the liquid state, via a process known as sublimation. At room temperature and ...

Heating and Cooling Curves

When a substance&#8212;isolated from its environment&#8212;is subjected to heat changes, corresponding changes in temperature and phase of the substance ...

Phase Diagrams

A phase diagram combines plots of pressure versus temperature for the liquid-gas, solid-liquid, and solid-gas phase-transition equilibria of a substance. ...

Use models to compare the phases of matter and the physical changes they undergo.

PS.PSc.1.2

physical-and-chemical-properties-of-matter

Physical and Chemical Properties of Matter

The characteristics that enable us to distinguish one substance from another are called properties.

Physical Properties of Matter

A physical property is ...

molecular-comparison-of-gases-liquids-and-solids

Molecular Comparison of Gases, Liquids, and Solids

Particles in a solid are tightly packed together (fixed shape) and often arranged in a regular pattern; in a liquid, they are close together with no ...

Intermolecular vs Intramolecular Forces

Intermolecular forces (IMF) are electrostatic attractions arising from charge-charge interactions between molecules. The strength of the intermolecular ...

Intermolecular Forces

Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions ...

comparing-intermolecular-forces-melting-point-boiling-point

Comparing Intermolecular Forces: Melting Point, Boiling Point, and Miscibility

Intermolecular forces are attractive forces that exist between molecules. They dictate several bulk properties, such as melting points, boiling points, ...

Carry out investigations to compare physical and chemical properties of matter.

PS.PSc.1.3

The Atomic Theory of Matter

The earliest recorded discussion of the basic structure of matter comes from ancient Greek philosophers. Leucippus and Democritus argued that all matter ...

Subatomic Particles

Dalton was only partially correct about the particles that make up matter. All matter is composed of atoms, and atoms are composed of three smaller ...

The Bohr Model

Following the work of Ernest Rutherford and his colleagues in the early twentieth century, the picture of atoms consisting of tiny dense nuclei surrounded ...

Emission Spectra

When solids, liquids, or condensed gases are heated sufficiently, they radiate some of the excess energy as light. Photons produced in this manner have a ...

The de Broglie Wavelength

In the macroscopic world, objects that are large enough to be seen by the naked eye follow the rules of classical physics. A billiard ball moving on a ...

The Uncertainty Principle

Werner Heisenberg considered the limits of how accurately one can measure properties of an electron or other microscopic particles. He determined that ...

Use models to interpret the data presented in Bohr diagrams and electron dot diagrams for neutral atoms of elements 1 through 18.

PS.PSc.1.4

Ions and Ionic Charges

In ordinary chemical reactions, the nucleus &mdash; which contains the protons and neutrons of each atom and thus identifies the element &mdash; remains ...

Use models to compare representations of atoms, ions, and isotopes.

PS.PSc.1.5

The Periodic Table

As early chemists discovered more elements, they realized that various elements could be grouped by their similar chemical behaviors. One such grouping ...

Periodic Classification of the Elements

The periodic table arranges atoms based on increasing atomic number so that elements with the same chemical properties recur periodically. When their ...

atomic-radii-and-effective-nuclear-charge

Atomic Radii and Effective Nuclear Charge

The elements in groups of the periodic table exhibit similar chemical behavior. This similarity occurs because the members of a group have the same number ...

Ionic Radii

Ionic radius is the measure used to describe the size of an ion. A cation always has fewer electrons and the same number of protons as the parent atom; it ...

Ionization Energy

The amount of energy required to remove the most loosely bound electron from a gaseous atom in its ground state is called its first ionization energy ...

Electron Affinity

The electron affinity (EA) is the energy change for adding an electron to a gaseous atom to form an anion (negative ion).



This process can be either ...

Alkali Metals

Group 1 elements are soft and shiny metallic solids. They are malleable, ductile, and good conductors of heat and electricity. The melting points of the ...

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. ...

Noble Gases


The elements in group 18 are noble gases (helium, neon, argon, krypton, xenon, and radon). They earned the name &ldquo;noble&rdquo; because they were ...

Use the Periodic Table as a model to predict the relative properties (metallic/nonmetallic character, ionic charge, and reactivity) and arrangement of elements based on the pattern of valence electrons in the outermost energy levels of atoms.

PS.PSc.1.6

Types of Chemical Bonds

Chemical bonding theories were pioneered by American chemist Gilbert&#xA0;N. Lewis. He developed a model called the Lewis model to explain the type and ...

Ionic Bonding and Electron Transfer

Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence ...

Covalent Bonding and Lewis Structures

Compared to ionic bonds, which results from the transfer of electrons between metallic and nonmetallic atoms, covalent bonds result from the mutual ...

Bonding in Metals

Metallic bonds are formed between two metal atoms. A simplified model to describe metallic bonding has been developed by Paul Dr&#xFC;de called the ...

Construct an explanation to classify the type of chemical bond that occurs (covalent, ionic, or metallic) in a given substance.

PS.PSc.2.1

Nomenclature of Alkanes

In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system ...

Nomenclature of Alkenes

The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of ...

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of ...

structure-and-nomenclature-of-alcohols-and-phenols

Structure and Nomenclature of Alcohols and Phenols

Overview 
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is ...

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two &#8212; ...

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic ...

IUPAC Nomenclature of Ketones

Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing &#8220;e&#8221; in the name of the longest hydrocarbon chain with ...

IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest ...

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the ...

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted ...

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (&#8211;NH2), ...

nomenclature-of-secondary-and-tertiary-amines

Nomenclature of Secondary and Tertiary Amines

The secondary and tertiary amines are derivatives of ammonia, where two and three of its hydrogens are replaced by alkyl groups, respectively. Secondary ...

nomenclature-of-aryl-and-heterocyclic-amines

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an &#8211;NH2 functionality directly attached to an aromatic ring. The name aniline is ...

Use models to apply International Union of Pure and Applied Chemistry (IUPAC) conventions to name and write formulas for simple compounds.

Understand types, properties, and structure of matter.

Naming Benzene Derivatives with One Group

Description

Transcript

Tags

More videos by Standards