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

Alkoller, bir karbon atomuna bağlı en az bir hidroksil fonksiyonel grubuna sahip bir organik molekül sınıfıdır. Metanol ve etanol iki tanıdık alkoldür. Her ikisi de alifatik alkollerdir, yani bir hidrokarbondan türetilirler ve bir benzen grubu içermezler.
Alifatik alkollerin üç sınıflandırması vardır. Birincisi, hidroksil grubunun bir karbon bazlı veya alkil grubuna bağlı bir karbon atomuna bağlı olduğu bir birincil alkoldür. İkincil bir alkolde, hidroksil grubu, iki alkil grubuna sahip bir karbon atomuna bağlanır. Son olarak, üçüncül bir alkolde, hidroksil grubu, üç alkil grubu olan bir karbon atomuna bağlanır.
Alkoller ayrıca, bir hidroksil grubunun doğrudan bir benzen halkasının karbonuna bağlandığı aromatik olabilir. Aromatik bir alkolün en basit şekli fenoldür. Fenol içeren bileşikler, fenol türevleri veya fenoller olarak bilinir.
Alkollerin maruz kaldığı belirli reaksiyonlar, reaksiyonun sonucundaki gözle görülür farklılıklara dayanarak onları ayırt etmek için kullanılabilir. Böyle bir reaksiyon, fenollerin varlığını test eden ferrik klorür testidir. Bir fenole ferrik klorür eklendiğinde, mor bir demir-üç fenol kompleksi oluşur. Bu, bir alifatik alkole eklendiğinde gözlenmez.
Bir başka yararlı reaksiyon, birincil ve ikincil alifatik alkolleri tanımlamak için kullanılan Jones Testidir. Sudaki sülfürik asit ve krom trioksit karışımı olan Jones reaktifi, güçlü bir oksitleyici ajandır. Aldehitler oluşturmak için birincil alkollerle reaksiyona girer - daha sonra karboksilik asitler oluşturur - ve ketonlar oluşturmak için ikincil alkollerle reaksiyona girer. Jones reaktifinin birincil ve ikincil alkollere eklenmesi, çözeltinin renklerin turuncudan koyu yeşile değişmesine neden olur. Üçüncül alkoller, oksidasyona dirençli oldukları için Jones reaktifi ile reaksiyona girmezler.
Son olarak Lucas testi ile alifatik alkolleri ayırt edebiliriz. Çinko klorür ve hidroklorik asidin bir karışımı olan Lucas reaktifi,bir SN1nükleofilik ikame reaksiyonu yoluyla ikincil ve üçüncül alkollerle reaksiyona girer. Çinko klorür, mükemmel bir ayrılma grubu oluşturmak için hidroksil oksijene koordine olur. Bir kez elimine edildikten sonra, pozitif yüklü bir karbokatyon kalır. Daha sonra, bir klor iyonu, suda çözünmeyen ve bulanık görünen bir alkil klorür oluşturmak için karbokatyona saldırır.
Üçüncül alkoller, oda sıcaklığında yağlı bir tabaka oluşturmak için Lucas reaktifi ile hemen reaksiyona girer. İkincil alkoller birkaç saniye ila birkaç dakika sonra pozitif sonuç verir. Birincil alkoller ısıtılmadıkları sürece olumsuz sonuç verir.
Bu laboratuvarda, bilinmeyen bir alkolü tanımlamak için ferrik klorür testi, Jones testi ve Lucas testini kullanacaksınız.

alkollerin tanımlanması

<h4>Alkol</h4>
Alkoller, günlük yaşamda geniş kapsamlı uygulamalara ve kullanımlara sahip oldukları için en tanınmış ve tanıdık olanlar arasında yer alan organik bileşiklerdir. Alkoller, bir alkil veya aril grubuna (ROH) bağlı bir hidroksil fonksiyonel grubu içeren organik moleküllerdir. Hidroksil karbonun yalnızca tek bir R grubu varsa, birincil alkol olarak bilinir. İki R grubuna sahipse ikincil alkoldür ve üç R grubuna sahipse üçüncül alkoldür. Diğer birçok organik bileşik gibi, alkoller de bir benzen halkası içererek aromatik olabilir. En basit aromatik alkol fenoldür.
Organik kimyada bir alkolün tanımlanması, alkol türlerinin farklı özelliklerinden yararlanılarak sağlanabilir. Nükleer manyetik rezonans (NMR) gibi çeşitli enstrümantasyon analiz yöntemleri kullanılabilirken, diğer kalitatif testler de kullanılabilir. Bu testleri bir araya getirerek, bir alkolün kimliği, aldehitlerin ve ketonların tanımlanma şekline benzer bir şekilde belirlenebilir.
<h4>Ferrik Klorür Testi</h4>
Alifatik alkol ile aromatik alkol arasında ayrım yapmanın bir yöntemi demir(III) klorür kullanmaktır. Demir klorür bileşiği çözeltiye kırmızı-turuncu bir görünüm verir. Fenol gibi bir aromatik alkolün varlığında, klorür atomları, merkez demir atomunun koordinasyon özelliğini değiştirerek aromatik alkol ile değiştirilir. Bu, çözeltinin rengini mor bir renge dönüştürür. Alifatik alkoller demir(III) klorür ile reaksiyona girmez ve bu nedenle çözelti kırmızı-turuncu kalır.
<h4>Jones Testi</h4>
Jones testi, güçlü bir oksitleyici ajan olarak işlev görmek için sülfürik asit varlığında krom trioksit kullanır. Jones reaktifinin varlığında, bir birincil alkol önce bir aldehite ve daha sonra bir karboksilik aside dönüştürülürken, ikincil bir alkol bir ketona oksitlenir. Kromun oksidasyon durumu bu testin anahtarıdır. Krom, Jones reaktifinde +6 oksidasyon durumundadır. Reaktifteki Cr(VI) kompleksleri ona parlak kırmızımsı, turuncu rengini verir.
Reaksiyon sürecinde, krom Cr (VI) 'dan +3 oksidasyon durumuna — Cr (III) indirgenir. İlk olarak, alkol ve kromik asit bir kromat ester oluşturur. Daha sonra, bir baz (H2O) alkolün CH bağını parçalayarak Cr (VI) 'yı Cr (IV) 'e indirerken karbonil grubunu oluşturur. Alkolün karbonu 2 elektronlu bir oksidasyona uğrar ve Cr(IV) 2 elektronlu bir indirgenmeye uğrar, bu nedenle bu bir indirgeme-oksidasyon aşamasıdır.
Cr(IV) daha ileri oksidasyon adımlarına katılır ve sonunda Cr(III)'e indirgenir. Cr(III) genellikle hekzaakuakrom (III) iyonları — [Cr(H2O)6]3+ — ve Cr (III) kompleksleri olarak bulunur, burada H2O molekülleri bir veya daha fazla sülfat iyonu ile değiştirilir - [Cr (H2O) 5 (SO4)]+. Bu kompleksler Cr (III)'e karakteristik yeşil rengi verir.
Üçüncül alkoller krom ile reaksiyona girmez ve bu nedenle çözeltiyi turuncu tutarak çökelti oluşmaz. Bu nedenle, Jones testi, birincil ve ikincil alkolleri üçüncül alkollerden ayırt etmeye yardımcı olabilir.
<h4>Lucas Testi</h4>
Lucas testi, reaktif olarak hidroklorik asit varlığında çinko(II) klorür kullanır. Bir alkolün varlığında, Lucas reaktifi alkolü halojenleştirerek sulu çözeltilerde çözünmeyen bir ürün haline getirecektir. Bunun için reaksiyon hızı, hidroksilin su olarak kaybının neden olduğu bir karbokatyon oluşumuna büyük ölçüde bağlıdır. Birincil alkol tarafından oluşturulan bir karbokatyon kararsızdır ve bu nedenle kolayca meydana gelmez. Bu, oda sıcaklığında gözlemlenebilir bir reaksiyonla sonuçlanmaz. Üçüncül bir alkol, stabil bir karbokatyon oluşturacak ve Lucas reaktifinin eklenmesi üzerine hızlı bir reaksiyona neden olacaktır. Bu, reaksiyon karışımında ikinci bir fazın ortaya çıkmasına neden olur, çünkü nihai halojenlenmiş ürün suda çözünmez. İkincil alkoller, üçüncül alkollerden daha az kararlı bir karbokatyon oluşturacaktır, ancak reaksiyon birkaç dakika içinde oda sıcaklığında gerçekleşecektir. Bu nedenle, Lucas Testi birincil, ikincil ve üçüncül alkoller arasında ayrım yapmaya yardımcı olabilir.
<h4>Başvuru</h4>
<ol>
	<li style="font-size:17px">Streitwieser, A., Heathcock, C.H., Kosower, E.M. (1998). Organik Kimyaya Giriş. Yukarı Saddle Nehri, NJ: Prentice Salonu.</li>
</ol>

Alkollerin Tanımlanması

Alkol
Alkoller, günlük yaşamda geniş kapsamlı uygulamalara ve kullanımlara sahip oldukları için en tanınmış ve tanıdık olanlar arasında yer alan organik bileşiklerdir ...

Education

JoVE Lab Manual

Chemistry

Kimya

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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Kimya laboratuvar temelleri için, hem eğitmenlere hem de öğrencilere yönelik, kapsamlı ve müfredat odaklı vidolar.

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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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Chemistry içinde Alkollerin Tanımlanması Eğitmen Hazırlığı - 13K+ Görüntülenme | JoVE Lab Manual

12 dakikalık bu öğrenci protokol videosunda Alkollerin Tanımlanması prosedürlerini adım adım takip edin. JoVE Lab Manual üzerindeki Chemistry koleksiyonunun bir parçasıdır.

Chemistry içinde Alkollerin Tanımlanması Öğrenci Protokolü - 87K+ Görüntülenme | JoVE Lab Manual

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SC.912.P.8.1

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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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