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

알코올은 탄소 원자에 연결된 적어도 하나의 수산기 작용기를 가진 유기 분자의 한 종류입니다. 메탄올과 에탄올은 두 가지 친숙한 알코올입니다. 둘 다 지방족 알코올로, 탄화수소에서 파생되며 벤젠기를 포함하지 않습니다.
지방족 알코올에는 세 가지 분류가 있습니다. 첫 번째는 1차 알코올로, 하이드록실기는 하나의 탄소 기반 또는 알킬기에 연결된 탄소 원자에 연결되어 있습니다. 2차 알코올에서 수산기는 두 개의 알킬기를 가진 탄소 원자에 연결됩니다. 마지막으로, 3차 알코올에서 수산기는 3개의 알킬기를 가진 탄소 원자에 연결됩니다.
알코올은 또한 방향족일 수 있으며, 수산기(hydroxyl group)는 벤젠 고리의 탄소에 직접 연결되어 있습니다. 방향족 알코올의 가장 간단한 형태는 페놀이 있습니다. 페놀을 함유하는 화합물은 페놀 유도체 또는 페놀이 알려져 있습니다.
알코올에 의해 겪은 특정 반응은 반응 결과의 눈에 띄는 차이에 기초하여 알코올을 구별하는 데 사용할 수 있습니다. 그러한 반응 중 하나는 페놀의 존재를 테스트하는 염화제이철 테스트입니다. 염화제이철이 페놀에 첨가되면 자주색 철-3-페놀 복합체가 형성됩니다. 이것은 지방족 알코올에 첨가될 때 관찰되지 않습니다.
또 다른 유용한 반응은 1차 및 2차 지방족 알코올을 식별하는 데 사용되는 Jones Test입니다. 물에 황산과 삼산화크롬이 혼합된 Jones의 시약은 강력한 산화제입니다. 1차 알코올과 반응하여 알데히드를 형성하고(알데히드는 카르복실산을 형성함) 2차 알코올과 반응하여 케톤을 형성합니다. Jones 시약을 1차 및 2차 알코올에 첨가하면 용액의 색이 주황색에서 짙은 녹색으로 변합니다. 3차 알코올은 산화에 내성이 있기 때문에 Jones의 시약과 반응하지 않습니다.
마지막으로, 루카스 테스트로 지방족 알코올을 구별할 수 있습니다. 염화아연과 염산의 혼합물인 Lucas' 시약은 SN1 친핵성 치환 반응을 통해 2차 및 3차 알코올과 반응합니다. 염화아연은 수산기 산소와 협조하여 우수한 이탈기를 생성합니다. 일단 제거되면 양전하를 띤 탄소양이온이 남습니다. 그런 다음 염소 이온이 탄소 양이온을 공격하여 물에 녹지 않고 탁하게 보이는 염화알킬을 형성합니다.
3차 알코올은 Lucas의 시약과 즉시 반응하여 실온에서 유성 층을 형성합니다. 2차 알코올은 몇 초에서 몇 분 후에 긍정적인 결과를 제공합니다. 1차 알코올은 가열하지 않으면 부정적인 결과를 제공합니다.
이 실험실에서는 염화철 테스트, Jones 테스트 및 Lucas 테스트를 사용하여 알려지지 않은 알코올을 식별합니다.

알코올 식별

<h4>알콜</h4>
알코올은 일상 생활에서 광범위한 응용 분야와 용도를 가지고 있기 때문에 가장 잘 알려져 있고 친숙한 유기 화합물입니다. 알코올은 알킬기 또는 아릴기(ROH)에 연결된 하이드록실 작용기를 포함하는 유기 분자입니다. 하이드록실 탄소가 단일 R기만 있는 경우 1차 알코올로 알려져 있습니다. R기가 2개 있으면 2차 알코올, R기가 3개 있으면 3차 알코올입니다. 다른 많은 유기 화합물과 마찬가지로 알코올도 벤젠 고리를 함유하여 방향족을 가질 수 있습니다. 가장 간단한 방향족 알코올은 페놀이 있습니다.
유기 화학에서 알코올을 식별하는 것은 알코올 유형의 다양한 특성을 활용하여 달성할 수 있습니다. 핵자기공명(NMR)과 같은 다양한 계측 분석 방법을 사용할 수 있지만 다른 정성 테스트도 활용할 수 있습니다. 이러한 테스트를 함께 결합하면 알데히드와 케톤을 식별할 수 있는 방법과 유사한 방식으로 알코올의 정체를 결정할 수 있습니다.
<h4>염화 제 2 철 시험</h4>
지방족 알코올과 방향족 알코올을 구별하는 한 가지 방법은 염화철(III)을 사용하는 것입니다. 염화철 화합물은 용액에 빨간색-주황색 모양을 제공합니다. 페놀과 같은 방향족 알코올이 존재하면 염화물 원자가 방향족 알코올로 대체되어 중심 철 원자의 배위 특성이 변경됩니다. 이렇게 하면 용액의 색상이 자주색으로 변경됩니다. 지방족 알코올은 염화철(III)과 반응하지 않으므로 용액은 빨간색-주황색으로 유지됩니다.
<h4>존스 테스트</h4>
Jones 테스트는 황산이 있는 상태에서 삼산화크롬을 사용하여 강력한 산화제로 작용합니다. Jones의 시약이 있는 상태에서 1차 알코올은 먼저 알데히드로 변환된 다음 카르복실산으로 전환되고 2차 알코올은 케톤으로 산화됩니다. 크롬의 산화 상태가 이 테스트의 핵심입니다. 크롬은 Jones의 시약에서 +6 산화 상태에 있습니다. 시약의 Cr(VI) 복합체는 밝은 붉은색, 주황색을 띱니다.
반응 과정에서 크롬은 Cr(VI)에서 +3 산화 상태인 Cr(III)로 환원됩니다. 첫째, 알코올과 크롬산은 크롬산염 에스테르를 형성합니다. 그런 다음, 염기 (H2O)는 알코올의 C-H 결합을 절단하여 Cr (VI)을 Cr (IV)로 환원시키면서 카르 보닐기를 형성합니다. 알코올의 탄소는 2전자 산화를 거치고 Cr(IV)은 2전자 환원을 거치므로 환원-산화 단계입니다.
Cr(IV)는 추가 산화 단계에 참여하고 결국 Cr(III)로 환원됩니다. Cr (III)은 종종 hexaaquachromium (III) 이온 ([Cr (H2O) 6] 3 + 및 Cr (III) 복합체로 존재하며, 여기서 H2O 분자는 하나 이상의 황산염 이온 ([Cr (H2O) 5 (SO4)]+로 대체됩니다. 이러한 복합체는 Cr (III)에 특징적인 녹색을 제공합니다.
3 차 알코올은 크롬과 반응하지 않으므로 침전물이 만들어지지 않아 용액을 주황색으로 유지합니다. 따라서 Jones 테스트는 1차 및 2차 알코올을 3차 알코올과 구별하는 데 도움이 될 수 있습니다.
<h4>루카스 테스트</h4>
Lucas 테스트는 염산이 있는 상태에서 염화아연(II)을 시약으로 사용합니다. 알코올이 있는 경우 Lucas 시약은 알코올을 할로겐화하여 수용액에 불용성 생성물을 만듭니다. 이에 대한 반응 속도는 수산기를 물로서 손실하여 발생하는 탄소 양이온의 형성에 크게 의존합니다. 1차 알코올에 의해 형성된 탄수화물 양이온은 불안정하므로 쉽게 발생하지 않습니다. 그 결과 실온에서 관찰할 수 있는 반응이 나타나지 않습니다. 3차 알코올은 안정적인 탄수화물 양이온을 형성하여 Lucas 시약을 첨가하면 빠른 반응을 일으킵니다. 그 결과 반응 혼합물에 두 번째 단계가 나타나는데, 이는 최종 할로겐화 생성물이 물에 불용성이기 때문입니다. 2차 알코올은 3차 알코올보다 덜 안정적인 탄소 양이온을 형성하지만 반응은 몇 분 안에 실온에서 발생합니다. 따라서 Lucas Test는 1차 알코올, 2차 알코올 및 3차 알코올을 구별하는 데 도움이 될 수 있습니다.
<h4>참조</h4>
<ol>
	<li style="font-size:17px">Streitwieser, A., Heathcock, C.H., Kosower, E.M. (1998). 유기 화학 소개. 어퍼 새들 리버, 뉴저지 : 프렌티스 홀.</li>
</ol>

알콜
알코올은 가장 잘 알아볼 수 있고 친숙한 유기 화합물로, 일상 생활에서 광범위한 응용 분야와 용도를 가지고 있습니다.

Education

교육

JoVE Lab Manual

Chemistry

화학

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

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Acids, Bases, and pH in Titration

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simple distillation

Separating Liquids by Boiling Point

Separating liquids by boiling point is the goal of distillation. A miscible mixture contains liquids that mix evenly, and it can be heated so that the more volatile liquid evaporates first. Volatility is a liquid’s tendency to vaporize, and boiling begins when bubbles form in the liquid phase. In a closed container, liquid and vapor can reach equilibrium, which means the rate of vaporization equals the rate of condensation. The pressure from the vapor above the liquid is called vapor pressure.

steam distillation

Steam Distillation and Low-Boiling Separation

Steam distillation is a separation method for temperature-sensitive organic compounds. It works best when the organic compound is immiscible in water, meaning the two liquids do not mix. The method helps remove the organic molecule from a non-volatile contaminant without using the higher temperatures needed for many other separations. In steam distillation, the immiscible mixture is heated until both water and the volatile organic compound distill together. The vapor rises to a condenser,...

thin-layer chromatography

TLC Separation by Polarity

Thin-layer chromatography (TLC) separates compounds in a mixture by polarity. It uses the same basic parts as other chromatography methods: a stationary phase, a mobile phase, and the solute. In TLC, the stationary phase is a thin coating on a plate instead of material packed into a column. The stationary phase in most TLC systems is polar silica gel, a form of silicon dioxide. Its surface has OH groups that can form hydrogen bonds. The sample is first spotted on a pencil start line with a...

column chromatography

Separating Mixtures by Polarity

Column chromatography separates compounds in an organic chemistry lab by using differences in physical properties. It is especially useful for microscale separations when less than 10 grams of material is available for analysis. The method can separate a mixture based on solubility, polarity, hydrophobicity, size, and charge. Any chromatography system has three main parts: the stationary phase, the mobile phase, and the sample mixture. In column chromatography, the stationary phase is usually...

hydrolysis of an ester

Soap Formation from Triglycerides

Triglycerides are lipids made of a glycerol backbone linked to three fatty acids. They are common in vegetable oils and animal fats. Plant lipids are the basis of vegetable oils, while animal lipids are used as lard or general sources of fats. A fatty acid has a long carbon chain, usually between 12 and 20 carbons, with a weak organic acid at one end. Some fatty acids contain double bonds. These are unsaturated fats. The double bond usually gives the chain a bent, cis shape. As a result,...

synthesis of luminol

Luminol Chemiluminescence in Forensics

Luminol chemiluminescence shows how a chemical reaction can produce light and help with blood detection. Chemical reactions may be endothermic or exothermic, depending on whether they absorb or release heat as reactants become products. The enthalpy of a reaction is the energy difference between reactants and products, or ΔH. A positive ΔH means the reaction is endothermic. A negative ΔH means it is exothermic. Many reactions do not happen in a single step. They can pass through intermediates...

esterification

Ester Formation and Everyday Fragrances

Esters are organic compounds with a carbonyl group attached to an oxygen that connects to another alkyl or aryl group. Their general formula is RCOOR'. They are often made by reacting a carboxylic acid with an alcohol in an esterification reaction. In this process, the hydroxyl group of the acid is replaced by an alkyl or aryl group. Many simple esters have familiar fruit and flower smells because their structures are small and less complex. Formic acid and methanol can combine to form methyl...

identification of unknown aldehydes and ketones

identification-of-unknown-aldehydes-and-ketones

Carbonyl Tests for Aldehydes and Ketones

Aldehydes and ketones are carbonyl compounds, which means they contain a C=O functional group. A ketone has two alkyl or aryl groups attached to the carbonyl carbon. Acetone is the simplest ketone, with two methyl groups. An aldehyde is similar, but it has at least one hydrogen attached to the carbonyl carbon. Formaldehyde is the simplest aldehyde, and acetaldehyde has one hydrogen and one methyl group. The carbonyl carbon in both aldehydes and ketones is electrophilic because the oxygen atom...

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

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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

7분 길이의 강사용 가이드를 통해 알코올 식별 수업을 준비하세요. JoVE Lab Manual의 Chemistry 실험을 위한 핵심 준비 단계를 다룹니다.

Chemistry의 알코올 식별 강사용 준비 - 13K+ 조회수 | JoVE Lab Manual

12분 길이의 학생 프로토콜 영상을 통해 알코올 식별 절차를 단계별로 따라 해보세요. JoVE Lab Manual의 Chemistry 컬렉션의 일부입니다.

Chemistry의 알코올 식별 학생 프로토콜 - 87K+ 조회수 | JoVE Lab Manual

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 ...

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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