Name: advanced functional groups in organic chemistry
Uploaded: 2023-04-30T18:28:33.000Z
Duration: 2 min 22 s
Channel: JoVE

K12 Standards

Minnesota Academic Standards in Science

9-12

Chemistry

3.2.2 9C.3.2.1.1

Overview of Advanced Functional Groups

Функциональные группы — это атомы или группы атомов в органическом соединении, которые придают им отличительные химические свойства. 
Одной из важных функциональных групп в органической химии является карбонильная функциональная группа, состоящая из атома углерода, дважды связанного с кислородом.
Два близкородственных органических соединения на основе карбонила — альдегиды и кетоны. В альдегидах карбонильный углерод связан с алкильной группой и атомом водорода. Исключение составляет формальдегид, в котором карбонильный углерод связан с двумя атомами водорода.
Между тем, в кетонах карбонильный атом углерода связан с двумя другими атомами углерода в углеводородном скелете.
Карбонильная группа входит в состав многих более крупных функциональных групп, таких как карбоксильная группа карбоновых кислот, которая состоит из гидроксильной группы, связанной с карбонильным углеродом.
К функциональным производным карбоновых кислот относятся сложные эфиры, в которых водород карбоксильной группы заменен алкильной группой; амиды, в которых ОН карбоксильной группы заменен на амин; и ацилхлориды, в которых ОН заменен хлоридом.
Множественные связи являются особенностью других функциональных групп, таких как нитрильная или цианофункциональная группа, в которой атом углерода трижды связан с азотом.
Бензол — это ароматический углеводород, который часто представлен в виде шести атомов углерода в кольце с чередующимися одинарными и двойными связями. Бензол минус один водород служит фенилом — функциональной группой. Гидроксильная группа, прикрепленная к ароматическому кольцу на основе фенила, образует фенол.
Амин — это неуглеродсодержащая функциональная группа, определяемая электроотрицательным атомом азота с единственной парой электронов, одиночно связанных в углеводородный каркас. Они классифицируются на первичные, вторичные и третичные, в зависимости от количества атомов углерода, связанных с азотом.
Аналогичным образом, фосфатная функциональная группа имеет атом фосфора, ковалентно связанный с четырьмя атомами кислорода. До трех углеводородных цепей могут быть присоединены к атомам кислорода, связанным по отдельности с фосфором, для получения органофосфатов.

Обзор расширенных функциональных групп

Функциональные группы — это группы атомов с определенными химическими свойствами, которые встречаются в органических молекулах и иногда обозначаются буквой «R». Функциональные группы могут «функционализировать» соединение, позволяя ему приобретать различные физические и химические свойства.

Типы расширенных функциональных групп

В таблице ниже приведены некоторые основные функциональные группы в органической химии.


<table style="margin-left: auto; margin-right: auto;">
 <tbody style="border: 1px solid black;">
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Класс органических соединений</td>
 <td style="color: black; border: 1px solid black; text-align: center;">Скелетные структуры соединений с функциональными группами, выделенными красным цветом</td>
 <td style="color: black; border: 1px solid black; text-align: center;">Названия соединений</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Ароматический углеводород</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure1" src="/files/ftp_upload/11717/11717_Figure_1.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Бензол</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Фенол</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure2" src="/files/ftp_upload/11717/11717_Figure_2.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Фенол (Гидроксибензол)</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Альдегид</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure3" src="/files/ftp_upload/11717/11717_Figure_3.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Этаналь (ацетальдегид)</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Кетон</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure4" src="/files/ftp_upload/11717/11717_Figure_4.svg" style="text-align: center; height: 70px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Ацетон</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Кислота или ацилхлорид</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure5" src="/files/ftp_upload/11717/11717_Figure_5.svg" style="text-align: center; height: 70px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Ацетилхлорид</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Карбоновая кислота</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure6" src="/files/ftp_upload/11717/11717_Figure_6.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Этановая кислота (Уксусная кислота)</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Эстер</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure7" src="/files/ftp_upload/11717/11717_Figure_7.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Ацетат этила</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Амин</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure8" src="/files/ftp_upload/11717/11717_Figure_8.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Этиламин</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Амид</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure9" src="/files/ftp_upload/11717/11717_Figure_9.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Ацетамид</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Нитрил</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure10" src="/files/ftp_upload/11717/11717_Figure_10.svg" style="text-align: center; height: 60px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Ацетонитрил</td>
 </tr>
 <tr>
 <td style="color: black; border: 1px solid black; text-align: center;">Фосфат</td>
 <td style="color: black; border: 1px solid black; text-align: center;"><img alt="Figure11" src="/files/ftp_upload/11717/11717_Figure_11.svg" style="text-align: center; height: 75px;"></td>
 <td style="color: black; border: 1px solid black; text-align: center;">Метилдигидрофосфат</td>
 </tr>
 </tbody>
</table>

Адаптированная версия текста<a href="https://openstax.org/books/chemistry-2e/pages/20-3-aldehydes-ketones-carboxylic-acids-and-esters"> Openstax, Chemistry 2e, Section 20.2: Alcohols and Ethers</a> and <a href="https://openstax.org/books/chemistry-2e/pages/20-4-amines-and-amides">Section 20.3: Aldehydes, Ketones, Carboxylic Acids, and Esters.</a>


Функциональные группы — это группы атомов с определенными химическими свойствами, которые встречаются в органических молекулах и иногда обозначаются как «R». ...

Education

JoVE Core

Organic Chemistry

Органическая химия

Unit 1

Раздел 1

Covalent Bonding and Structure

Ковалентная связь и структура

KEY TERMS AND CONCEPTS

ОСНОВНЫЕ ТЕРМИНЫ И ПОНЯТИЯ

advanced functional groups in organic chemistry

Advanced functional groups are atom clusters in organic molecules that give those molecules specific chemical properties. They are sometimes shown as &quot;R&quot; in formulas. By changing the atoms attached to a carbon skeleton, a functional group can make a compound behave differently in physical and chemical reactions.

This topic covers several major classes of organic compounds with advanced functional groups. Aromatic hydrocarbons include benzene. Phenol is another example and is also called hydroxybenzene. The set also includes aldehydes such as ethanal, or acetaldehyde, and ketones such as acetone.

Other important examples are acid or acyl chlorides, carboxylic acids, esters, amines, amides, nitriles, and phosphates. Acetyl chloride is an acid or acyl chloride. Ethanoic acid, also called acetic acid, is a carboxylic acid, and ethyl acetate is an ester. Ethylamine is an amine, acetamide is an amide, acetonitrile is a nitrile, and methyl dihydrogen phosphate is a phosphate.

These examples show how the same carbon framework can belong to different compound classes depending on the functional group present. The structures in the table highlight the functional group in red so it is easy to identify the key part of each molecule. This content is adapted from OpenStax Chemistry 2e, including sections on alcohols and ethers, aldehydes and ketones, and carboxylic acids and esters.

Advanced Functional Groups in Organic Chemistry

advanced-functional-groups-in-organic-chemistry

what is organic chemistry?

Carbon Compounds in Everyday Life

Organic chemistry focuses on carbon compounds called organic compounds. These compounds may come from living things or be made by chemists. Carbon is the main element in them, and it bonds with other carbon atoms as well as hydrogen, oxygen, nitrogen, and sulfur. Carbon can form up to four strong bonds. That ability lets carbon atoms build chains and rings of many sizes, shapes, and levels of complexity. Not every carbon-containing substance is classified as organic. Carbonates, cyanides, and...

electronic structure of atoms

Atomic Orbitals and Quantum Numbers

Atomic orbitals and quantum numbers describe how electrons are arranged around the nucleus. An atom has a small, positively charged nucleus with electrons surrounding it. The nucleus contains protons and neutrons, and the quantum mechanical model gives a better picture of this structure than older models. Protons carry a +1 charge and have a mass of 1.0073 amu. Neutrons have no charge and have a mass of 1.0087 amu. Electrons carry a −1 charge and have a mass of 0.00055 amu. The number of...

electron configurations

How Electrons Fill Atomic Orbitals

Electron filling in atoms follows a set order based on orbital energy. The Aufbau principle says each new electron enters the lowest-energy subshell available. The Pauli exclusion principle says no two electrons can share the same set of four quantum numbers. Hund’s rule of maximum multiplicity says electrons stay unpaired in equal-energy orbitals when possible. The order of filling follows the relative energies of the subshells. A common sequence is 1s, 2s, 2p, 3s, 3p, 4s, 3d, 4p, and so on.

chemical bonds

Chemical Bonds: Types and Strength

Chemical bonds help atoms reach a full valence shell like the nearest noble gas. The main bond types are ionic, covalent, and metallic. Bond energy and bond length also help explain how strong a bond is. An ionic bond forms from electrostatic attraction between cations and anions. In many cases, one atom transfers electrons to another atom, and the ions form from that transfer. Ionic bonds have no defined direction because the attraction spreads evenly through three-dimensional space. A...

polar covalent bonds

Electronegativity in Polar Covalent Bonds

Polar covalent bonds form when atoms share electrons unevenly. This happens in covalent bonds between atoms that have similar, but not identical, tendencies to attract electrons. Nonmetal atoms often make these bonds with other nonmetals. Hydrogen gas, H2, is a simple example of a covalent bond between two hydrogen atoms. A covalent bond begins when two atoms move close enough for their valence orbitals to overlap. In hydrogen, the 1s orbitals overlap and the single electrons on each atom...

lewis structures and formal charges

Lewis Structures, Bonds, and Formal Charge

Lewis structures show how atoms share electrons in covalent bonds and in polyatomic ions. Lewis symbols help draw these structures, and the periodic table helps predict how many valence electrons an atom has and how many bonds it can form to reach an octet. Group 18 elements, such as argon and helium, already have filled electron configurations. They rarely take part in chemical bonding. Atoms in group 17, such as bromine and iodine, need one more electron to reach an octet, so they can form...

vsepr theory

Molecular Shapes from Electron Pairs

Molecular shape can be predicted from the way electron pairs arrange around a central atom. Valence shell electron-pair repulsion theory, or VSEPR theory, uses a Lewis structure to count bonding pairs and lone electron pairs. The main idea is simple: electron pairs spread out as far as possible to reduce repulsion. In a molecule, the valence electrons around the central atom can be bonding pairs or lone pairs. Bonding pairs are found mainly between bonded atoms. Lone pairs stay on one atom and...

molecular geometry and dipole moments

Predicting Shape and Molecular Polarity

Molecular shape and molecular polarity can be predicted with VSEPR theory and dipole moments. Start by writing the Lewis structure of the molecule or polyatomic ion. Then count the electron groups around the central atom. Lone pairs and bonds both count as electron groups, and a single, double, or triple bond each counts as one region of electron density. Use that count to identify the electron-pair geometry. Next, use the number of lone pairs to determine the molecular structure. If more than...

resonance and hybrid structures

Resonance in Nitrite and Carbonate Ions

Resonance explains why some Lewis structures do not match the measured properties of a molecule or ion. When two or more Lewis structures have the same atom arrangement, the real electron distribution is an average of the structures shown. The nitrite anion, NO2−, is one example. It can be drawn in two ways, with the N–O and N=O bonds in different places. If nitrite had one single bond and one double bond, the two bond lengths should be different, because a double bond is shorter and stronger...

valence bond theory and hybridized orbitals

valence-bond-theory-and-hybridized-orbitals

Covalent Bond Overlap and Orbital Hybridization

Covalent bonds form when orbitals on two atoms overlap and their single electrons pair up. The bond is stronger when the overlap is greater. Maximum overlap happens when the orbitals meet along a direct line between the two nuclei. A sigma bond, or σ bond, is the kind of covalent bond found in a single bond in a Lewis structure. In a σ bond, electron density is concentrated along the internuclear axis. A pi bond, or π bond, forms when two p orbitals overlap side by side. In a π bond, the...

mo theory and covalent bonding

Bond Order and Molecular Orbitals

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intermolecular forces and physical properties

intermolecular-forces-and-physical-properties

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solubility

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Solution formation depends on how solutes and solvents interact. A solution is a homogeneous mixture made of a solvent, which is the larger part, and a solute, which is the smaller part. The physical state of a solution is usually the same as the solvent. Concentration is often described as dilute for a low amount of solute or concentrated for a high amount of solute. When a solute dissolves, its particles are surrounded by solvent species. This process is called solvation. If water is the...

introduction to functional groups

Functional Groups and Organic Molecules

Functional groups are groups of atoms with specific chemical properties that appear within organic molecules. They are sometimes shown as "R." These groups sit along the carbon backbone of macromolecules, which can form chains or rings of carbon atoms. Functional groups help functionalize a compound. That means they can give the molecule different physical and chemical properties. In organic chemistry, this change in group structure can strongly affect how a compound behaves. Common...

overview of advanced functional groups

Advanced functional groups are atom clusters in organic molecules that give those molecules specific chemical properties. They are sometimes shown as "R" in formulas. By changing the atoms attached to a carbon skeleton, a functional group can make a compound behave differently in physical and chemical reactions. This topic covers several major classes of organic compounds with advanced functional groups. Aromatic hydrocarbons include benzene. Phenol is another example and is also called...

key terms and concepts

Learn how advanced functional groups change the properties of organic molecules, with examples including aldehydes, ketones, esters, amines, and more.

Advanced Functional Groups in Organic Chemistry | JoVE K12

organic chemistry

JoVE Core Organic Chemistry explains basic concepts of stereochemistry, reactions, and mechanisms using concise and easy-to-understand animated video lessons. Additionally, the scientist-in-action videos demonstrate the application of related concepts in classical and original research experiments performed in today's laboratories worldwide.

Florida Department of Education

High School

Physical Science

SC.912.P.8

SC.912.P.8.13

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Advanced Functional Groups in Organic Chemistry

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