Name: alcohol tests for primary, secondary, and tertiary
Uploaded: 2020-03-26T07:22:29.000Z
Duration: 3 min 32 s
Channel: JoVE

K12 Standards

Florida Department of Education

High School

Physical Science

SC.912.P.8

SC.912.P.8.13

Identifying Alcohols

Спирты — это класс органических молекул, обладающих по крайней мере одной гидроксильной функциональной группой, связанной с атомом углерода. Метанол и этанол – два привычных спирта. Оба являются алифатическими спиртами, что означает, что они получены из углеводорода и не содержат бензольной группы.
Существует три классификации алифатических спиртов. Первый — это первичный спирт, в котором гидроксильная группа соединена с атомом углерода, который соединен с одной углеродной или алкильной группой. Во вторичном спирте гидроксильная группа соединена с атомом углерода, который имеет две алкильные группы. Наконец, в третичном спирте гидроксильная группа соединена с атомом углерода с тремя алкильными группами.
Спирты также могут быть ароматическими, в которых гидроксильная группа соединена непосредственно с углеродом бензольного кольца. Самой простой формой ароматического алкоголя является фенол. Соединения, содержащие фенол, известны как производные фенола или фенолы.
Определенные реакции, которым подвергаются спирты, могут быть использованы для их различения на основе видимых различий в исходе реакции. Одной из таких реакций является тест на хлорид железа, который проверяет наличие фенолов. При добавлении хлорида железа к фенолу образуется фиолетовый железо-трехфенольный комплекс. Этого не наблюдается при добавлении его в алифатический спирт.
Еще одной полезной реакцией является тест Джонса, который используется для определения первичных и вторичных алифатических спиртов. Реагент Джонса, представляющий собой смесь серной кислоты и триоксида хрома в воде, является сильным окислителем. Он реагирует с первичными спиртами с образованием альдегидов, которые затем образуют карбоновые кислоты, и реагирует со вторичными спиртами с образованием кетонов. Добавление реагента Джонса в первичные и вторичные спирты приводит к тому, что раствор меняет цвет с оранжевого на темно-зеленый. Третичные спирты не вступают в реакцию с реагентом Джонса, поскольку они устойчивы к окислению.
Наконец, мы можем различить алифатические спирты с помощью теста Лукаса. Реагент Лукаса, представляющий собой смесь хлорида цинка и соляной кислоты, реагирует со вторичными и третичными спиртами посредством реакции нуклеофильного замещения SN1. Хлорид цинка координируется с гидроксильным кислородом, образуя отличную группу ухода. После устранения положительно заряженный карбокатион остается. Затем ион хлора атакует карбокатион, образуя алкилхлорид, который нерастворим в воде и выглядит мутным.
Третичные спирты немедленно вступают в реакцию с реагентом Лукаса, образуя маслянистый слой при комнатной температуре. Вторичные спирты дают положительный результат уже через несколько секунд или нескольких минут. Первичные спирты дают отрицательный результат, если их не нагревать.
В этой лаборатории вы будете использовать тест на хлорид железа, тест Джонса и тест Лукаса для определения неизвестного алкоголя.

Идентификация спиртов

<h4>Спирты</h4>
Спирты — это органические соединения, которые являются одними из самых узнаваемых и знакомых, поскольку они имеют широкий спектр применения и использования в повседневной жизни. Спирты представляют собой органические молекулы, содержащие гидроксильную функциональную группу, связанную с алкильной или арильной группой (ROH). Если гидроксильный углерод имеет только одну R-группу, он известен как первичный спирт. Если у него есть две Р-группы, то это вторичный спирт, а если три Р-группы, то это третичный спирт. Как и многие другие органические соединения, спирты также могут быть ароматическими, поскольку содержат бензольное кольцо. Самым простым ароматическим алкоголем является фенол.
Идентификация спирта в органической химии может быть достигнута путем использования различных свойств типов спиртов. В то время как можно использовать различные методы анализа приборов, такие как ядерный магнитный резонанс (ЯМР), можно использовать и другие качественные тесты. Объединив эти тесты вместе, идентичность алкоголя может быть определена таким же образом, как и альдегиды и кетоны.
<h4>Тест на хлорид железа</h4>
Одним из методов дифференциации между алифатическим спиртом и ароматическим спиртом является использование хлорида железа (III). Соединение хлорида железа придает раствору красно-оранжевый вид. В присутствии ароматического спирта, такого как фенол, атомы хлорида заменяются ароматическим спиртом, изменяя координационное свойство центрального атома железа. При этом цвет раствора меняется на фиолетовый. Алифатические спирты не вступают в реакцию с хлоридом железа (III) и, таким образом, раствор остается красно-оранжевым.
<h4>Тест Джонса</h4>
В тесте Джонса триоксид хрома используется в присутствии серной кислоты, которая действует как мощный окислитель. В присутствии реагента Джонса первичный спирт сначала превращается в альдегид, а затем в карбоновую кислоту, в то время как вторичный спирт окисляется в кетон. Степень окисления хрома является ключом к этому испытанию. Хром находится в степени окисления +6 в реагенте Джонса. Комплексы Cr(VI) в составе реагента придают ему яркий красноватый, оранжевый цвет.
В процессе реакции хром восстанавливается из Cr(VI) до +3 степени окисления — Cr(III). Во-первых, спирт и хромовая кислота образуют сложный эфир хромата. Затем основание (H2O) расщепляет связь C-H спирта, образуя карбонильную группу, восстанавливая Cr(VI) до Cr(IV). Углерод спирта подвергается 2-электронному окислению, а Cr(IV) — 2-электронному восстановлению, так что это стадия восстановления-окисления.
Cr(IV) участвует в дальнейших стадиях окисления и в конечном итоге восстанавливается до Cr(III). Cr(III) часто присутствует в виде ионов гексааквахромия(III) — [Cr(H2O)6]3+ — и комплексов Cr(III), где молекулы H2O замещены одним или несколькими сульфатными ионами — [Cr(H2O)5(SO4)]+. Эти комплексы придают Cr(III) характерный зеленый цвет.
Третичные спирты не вступают в реакцию с хромом, и поэтому осадок не образуется, сохраняя раствор оранжевым. Таким образом, тест Джонса может помочь дифференцировать первичные и вторичные спирты от третичных.
<h4>Тест Лукаса</h4>
В тесте Лукаса в качестве реагента используется хлорид цинка(II) в присутствии соляной кислоты. В присутствии спирта реагент Лукаса будет галогенировать спирт, превращая его в нерастворимый продукт в водных растворах. Скорость реакции при этом сильно зависит от образования карбокатиона, вызванного потерей гидроксила в виде воды. Карбокатион, образованный первичным спиртом, нестабилен и, следовательно, не может быть быстрым. Это приводит к отсутствию наблюдаемой реакции при комнатной температуре. Третичный спирт образует стабильный карбокатион, что приводит к быстрой реакции при добавлении реагента Лукаса. Это приводит к появлению второй фазы в реакционной смеси, поскольку конечный галогенированный продукт нерастворим в воде. Вторичные спирты образуют менее устойчивый карбокатион, чем третичные спирты, но реакция произойдет при комнатной температуре в считанные минуты. Таким образом, тест Лукаса может помочь дифференцировать первичные, вторичные и третичные спирты.
<h4>Ссылки</h4>
<ol>
	<li style="font-size:17px">Streitwieser, A., Heathcock, C.H., Kosower, E.M. (1998). Введение в органическую химию. Аппер Сэддл Ривер, Нью-Джерси: Прентис Холл.</li>
</ol>

Спирты
Спирты - это органические соединения, которые являются одними из самых узнаваемых и знакомых, поскольку они имеют широкий спектр применения и использования в повседневной жизни.

Education

JoVE Lab Manual

Chemistry

Химия

alcohol tests for primary, secondary, and tertiary

Alcohol tests can help sort alcohols by structure and reactivity. Alcohols are organic molecules with a hydroxyl group attached to an alkyl or aryl group, written as ROH. If the carbon with the hydroxyl group has one R group, the alcohol is primary. If it has two R groups, it is secondary. If it has three R groups, it is tertiary.

Alcohols can also be aromatic when they contain a benzene ring. Phenol is the simplest aromatic alcohol. To identify an alcohol, chemists can use its chemical behavior instead of relying only on instrument-based methods such as NMR. By combining several qualitative tests, the identity of an alcohol can be determined in a way similar to how aldehydes and ketones are identified.

The ferric chloride test helps tell aromatic alcohols from aliphatic alcohols. Iron(III) chloride starts as a red-orange solution. If an aromatic alcohol such as phenol is present, the chloride atoms are replaced and the solution turns purple. Aliphatic alcohols do not react in this test, so the color stays red-orange.

The Jones test uses chromium trioxide with sulfuric acid as a strong oxidizing reagent. A primary alcohol is oxidized first to an aldehyde and then to a carboxylic acid. A secondary alcohol is oxidized to a ketone. Chromium starts in the +6 oxidation state, which gives the reagent its reddish-orange color, and is reduced to Cr(III), which is green. Tertiary alcohols do not react, so the solution remains orange. This makes the Jones test useful for separating primary and secondary alcohols from tertiary alcohols.

The Lucas test uses zinc(II) chloride in hydrochloric acid. It halogenates the alcohol and produces an insoluble product in water. The test depends on carbocation formation when the hydroxyl group leaves as water. Primary alcohols do not show a visible reaction at room temperature because their carbocations are unstable. Tertiary alcohols react quickly because their carbocations are more stable, and a second layer appears. Secondary alcohols react more slowly and usually take a few minutes. This test helps distinguish primary, secondary, and tertiary alcohols.

Alcohol Tests for Primary, Secondary, and Tertiary

alcohol-tests-for-primary-secondary-and-tertiary

lab techniques

Measuring with Accuracy in the Lab

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Balancing Equations and Reactant Limits

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Oxidation States in Redox Reactions

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acid and base concentrations

Acids, Bases, and pH in Titration

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enthalpy of reaction

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solubility

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beer's law

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concentration dependence

Reaction Order and Rate Constants

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temperature dependence

Reaction Rate, Arrhenius, and Catalysts

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galvanic cells

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basic organic chemistry techniques

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melting points

How Impurities Change Melting Points

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boiling points

Boiling Point and Vapor Pressure

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recrystallization

Purifying Crystals by Solubility

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extraction

Separating Mixtures with Solvent Extraction

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simple distillation

Separating Liquids by Boiling Point

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steam distillation

Steam Distillation and Low-Boiling Separation

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thin-layer chromatography

TLC Separation by Polarity

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column chromatography

Separating Mixtures by Polarity

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hydrolysis of an ester

Soap Formation from Triglycerides

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synthesis of luminol

Luminol Chemiluminescence in Forensics

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esterification

Ester Formation and Everyday Fragrances

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identification of unknown aldehydes and ketones

identification-of-unknown-aldehydes-and-ketones

Carbonyl Tests for Aldehydes and Ketones

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uv-vis spectroscopy of dyes

How Dyes Absorb Visible Light

Dyes absorb visible light because their molecular structure lets them interact with specific wavelengths. When light hits a substance, some light is absorbed and the rest is reflected or transmitted. The color we see depends on the wavelength that is reflected. A blue substance reflects blue light, around 430 to 480 nm, and absorbs the complementary orange region, around 590 to 630 nm. Compounds that do not absorb in the visible range appear colorless to the human eye. Light also has energy and...

identifying alcohols

Alcohol tests can help sort alcohols by structure and reactivity. Alcohols are organic molecules with a hydroxyl group attached to an alkyl or aryl group, written as ROH. If the carbon with the hydroxyl group has one R group, the alcohol is primary. If it has two R groups, it is secondary. If it has three R groups, it is tertiary. Alcohols can also be aromatic when they contain a benzene ring. Phenol is the simplest aromatic alcohol. To identify an alcohol, chemists can use its chemical...

chemistry

Comprehensive, curriculum-focused videos for both instructors and students in introductory chemistry lab courses.

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Learn how ferric chloride, Jones, and Lucas tests distinguish aromatic, primary, secondary, and tertiary alcohols using color change and reaction rate.

Alcohol Tests for Primary, Secondary, and Tertiary | JoVE K12

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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, ...

States of Matter

Solids, liquids, and gases are the three states of matter commonly found on Earth. A solid is rigid and possesses a definite shape. A liquid flows and ...

States of Matter and Phase Changes

The internal energy of a substance&#8212;the total kinetic energy of all its molecules and the potential energy of their associated forces&#8212;depends ...

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 ...

Differentiate between physical and chemical properties and physical and chemical changes of matter.

SC.912.P.8.1

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 ...

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. ...

SC.912.P.8.2

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 Wave Nature of Light

The nature of light has been a subject of inquiry since antiquity. In the seventeenth century, Isaac Newton performed experiments with lenses and prisms ...

The Electromagnetic Spectrum

The electromagnetic spectrum consists of all the types of electromagnetic radiation arranged according to their frequency and wavelength. Each of the ...

Interference and Diffraction

Interference is a characteristic phenomenon exhibited by waves. When two electromagnetic waves interact with their peaks and troughs coinciding, a ...

Photoelectric Effect

When light of a particular wavelength strikes a metal surface, electrons are emitted. This is called the photoelectric effect. The minimum frequency of ...

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 ...

The Quantum-Mechanical Model of an Atom

Shortly after de Broglie published his ideas that the electron in a hydrogen atom could be better thought of as being a circular standing wave instead of ...

Explore the scientific theory of atoms (also known as atomic theory) by describing changes in the atomic model over time and why those changes were necessitated by experimental evidence.

SC.912.P.8.3

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 ...

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 ...

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 ...

Atomic Mass

Atoms &mdash; and the protons, neutrons, and electrons that compose them &mdash; are extremely small. For example, a carbon atom weighs less than 2 ...

Atomic Number and Mass Number

The number of protons in the nucleus of an atom is its atomic number (Z). This is the defining trait of an element. Its value determines the identity of ...

Explore the scientific theory of atoms (also known as atomic theory) by describing the structure of atoms in terms of protons, neutrons and electrons, and differentiate among these particles in terms of their mass, electrical charges and locations within the atom.

SC.912.P.8.4

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 ...

Electron Configurations

Electron configurations and orbital diagrams can be determined by applying the Aufbau principle (each added electron occupies the subshell of lowest ...

Electronic Structure of Atoms


An atom comprises protons and neutrons, which are contained inside the dense, central&#160;core called the nucleus, with electrons present around the ...

Electron Behavior

Electrons are negatively charged subatomic particles that are attracted to an orbit around the positively-charged nucleus of an atom. They reside in ...

Relate properties of atoms and their position in the periodic table to the arrangement of their electrons.

SC.912.P.8.5

A. A working definition of matter is that it takes up space, has mass, and has measurable properties. Matter is comprised of atomic, subatomic, and elementary particles.

B. Electrons are key to defining chemical and some physical properties, reactivity, and molecular structures. Repeating (periodic) patterns of physical and chemical properties occur among elements that define groups of elements with similar properties. The periodic table displays the repeating patterns, which are related to the atom's outermost electrons. Atoms bond with each other to form compounds.

C. In a chemical reaction, one or more reactants are transformed into one or more new products. Many factors shape the nature of products and the rates of reaction. 

D. Carbon-based compounds are building-blocks of known life forms on earth and numerous useful natural and synthetic products.

Alcohol Tests for Primary, Secondary, and Tertiary

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