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

Les alcools sont une classe de molécules organiques possédant au moins un groupe fonctionnel hydroxyle lié à un atome de carbone. Le méthanol et l’éthanol sont deux alcools familiers. Les deux sont des alcools aliphatiques, c’est-à-dire qu’ils sont dérivés d’un hydrocarbure et ne contiennent pas de groupe benzène.
Il existe trois classifications d’alcools aliphatiques. Le premier est un alcool primaire, où le groupe hydroxyle est connecté à un atome de carbone qui est connecté à un groupe à base de carbone, ou alkyle. Dans un alcool secondaire, le groupe hydroxyle est lié à un atome de carbone qui a deux groupes alkyles. Enfin, dans un alcool tertiaire, le groupe hydroxyle est relié à un atome de carbone avec trois groupes alkyle.
Les alcools peuvent également être aromatiques, dans lesquels un groupe hydroxyle est relié directement au carbone d’un cycle benzénique. La forme la plus simple d’un alcool aromatique est le phénol. Les composés qui contiennent du phénol sont connus sous le nom de dérivés de phénol ou phénols.
Certaines réactions subies par les alcools peuvent être utilisées pour les distinguer en fonction des différences visibles dans le résultat de la réaction. L’une de ces réactions est le test au chlorure ferrique, qui teste la présence de phénols. Lorsque du chlorure ferrique est ajouté à un phénol, un complexe fer-trois-phénol violet se forme. Cela n’est pas observé lorsqu’il est ajouté à un alcool aliphatique.
Une autre réaction utile est le test de Jones, qui est utilisé pour identifier les alcools aliphatiques primaires et secondaires. Le réactif de Jones, un mélange d’acide sulfurique et de trioxyde de chrome dans l’eau, est un puissant agent oxydant. Il réagit avec les alcools primaires pour former des aldéhydes - qui forment ensuite des acides carboxyliques - et il réagit avec les alcools secondaires pour former des cétones. L’ajout du réactif Jones aux alcools primaires et secondaires fait changer la couleur de la solution, passant de l’orange au vert foncé. Les alcools tertiaires ne réagissent pas avec le réactif de Jones car ils résistent à l’oxydation.
Enfin, on peut distinguer les alcools aliphatiques avec le test de Lucas. Le réactif de Lucas, qui est un mélange de chlorure de zinc et d’acide chlorhydrique, réagit avec les alcools secondaires et tertiaires par une réaction de substitution nucléophile SN1. Le chlorure de zinc se coordonne avec l’hydroxyle oxygène pour générer un excellent groupe de départ. Une fois éliminé, il reste une carbocation chargée positivement. Ensuite, un ion chlore attaque le carbocation pour former un chlorure d’alkyle, qui est insoluble dans l’eau et semble trouble.
Les alcools tertiaires réagissent immédiatement avec le réactif de Lucas pour former une couche huileuse à température ambiante. Les alcools secondaires donnent un résultat positif après quelques secondes à quelques minutes. Les alcools primaires donnent un résultat négatif à moins qu’ils ne soient chauffés.
Dans ce laboratoire, vous utiliserez le test du chlorure ferrique, le test de Jones et le test de Lucas pour identifier un alcool inconnu.

identification des alcools

<h4>Alcools</h4>
Les alcools sont des composés organiques qui sont parmi les plus reconnaissables et les plus familiers, car ils ont un large éventail d’applications et d’utilisations dans la vie quotidienne. Les alcools sont des molécules organiques contenant un groupe fonctionnel hydroxyle lié à un groupe alkyle ou aryle (ROH). Si le carbone hydroxyle n’a qu’un seul groupe R, il est connu sous le nom d’alcool primaire. S’il a deux groupes R, c’est un alcool secondaire, et s’il a trois groupes R, c’est un alcool tertiaire. Comme beaucoup d’autres composés organiques, les alcools peuvent également être aromatiques en contenant un cycle benzénique. L’alcool aromatique le plus simple est le phénol.
L’identification d’un alcool en chimie organique peut être réalisée en exploitant les différentes propriétés des types d’alcools. Bien que diverses méthodes d’analyse d’instruments, telles que la résonance magnétique nucléaire (RMN), puissent être utilisées, d’autres tests qualitatifs peuvent également être utilisés. En couplant ces tests, l’identité d’un alcool peut être déterminée de la même manière que les aldéhydes et les cétones peuvent être identifiés.
<h4>Test de chlorure ferrique</h4>
Une méthode pour différencier un alcool aliphatique d’un alcool aromatique consiste à utiliser du chlorure de fer(III). Le composé de chlorure de fer donne à la solution un aspect rouge-orange. En présence d’un alcool aromatique, comme le phénol, les atomes de chlorure sont remplacés par l’alcool aromatique, modifiant la propriété de coordination de l’atome de fer central. Cela change la couleur de la solution en une couleur violette. Les alcools aliphatiques ne réagissent pas avec le chlorure de fer(III) et, par conséquent, la solution reste rouge-orange.
<h4>Test de Jones</h4>
Le test de Jones utilise du trioxyde de chrome en présence d’acide sulfurique pour agir comme un puissant agent oxydant. En présence du réactif de Jones, un alcool primaire est d'abord converti en aldéhyde, puis en acide carboxylique, tandis qu'un alcool secondaire sera oxydé en cétone. L’état d’oxydation du chrome est la clé de ce test. Le chrome est à l'état d'oxydation +6 dans le réactif de Jones. Les complexes Cr(VI) présents dans le réactif lui donnent sa couleur rougeâtre et orange vif.
Au cours de la réaction, le chrome est réduit de Cr(VI) à l’état d’oxydation +3 - Cr(III). Tout d’abord, l’alcool et l’acide chromique forment un ester de chromate. Ensuite, une base (H2O) clive la liaison C-H de l’alcool, formant le groupe carbonyle tout en réduisant Cr(VI) en Cr(IV). Le carbone de l’alcool subit une oxydation à 2 électrons, et le Cr(IV) subit une réduction à 2 électrons, il s’agit donc d’une étape d’oxydation réductrice.
Le Cr(IV) participe à d’autres étapes d’oxydation et est finalement réduit en Cr(III). Cr(III) est souvent présent sous forme d’ions hexaaquachrome(III) — [Cr(H2O)6]3+ — et de complexes Cr(III), où les molécules H2O sont remplacées par un ou plusieurs ions sulfates — [Cr(H2O)5(SO4)]+. Ces complexes donnent au Cr(III) la couleur verte caractéristique.
Les alcools tertiaires ne réagissent pas avec le chrome, et donc aucun précipité n’est fabriqué, ce qui maintient la solution orange. Par conséquent, le test de Jones peut aider à différencier les alcools primaires et secondaires des alcools tertiaires.
<h4>Test de Lucas</h4>
Le test Lucas utilise du chlorure de zinc(II) en présence d’acide chlorhydrique comme réactif. En présence d’un alcool, le réactif Lucas va halogéner l’alcool, produisant un produit insoluble dans des solutions aqueuses. La vitesse de réaction pour cela dépend fortement de la formation d’un carbocation causé par la perte de l’hydroxyle sous forme d’eau. Un carbocation formé par un alcool primaire est instable et ne se produira donc pas facilement. Il n’en résulte aucune réaction observable à température ambiante. Un alcool tertiaire formera un carbocation stable, entraînant une réaction rapide lors de l’ajout du réactif Lucas. Il en résulte l’apparition d’une deuxième phase dans le mélange réactionnel car le produit halogéné final est insoluble dans l’eau. Les alcools secondaires formeront un carbocation moins stable que les alcools tertiaires, mais la réaction se produira à température ambiante en quelques minutes. Par conséquent, le test Lucas peut aider à différencier les alcools primaires, secondaires et tertiaires.
<h4>références</h4>
<ol>
	<li style="font-size :17px">Streitwieser, A., Heathcock, C.H., Kosower, E.M. (1998). Introduction à la chimie organique. Upper Saddle River, NJ : Prentice Hall.</li>
</ol>

Identification des alcools

Alcools
Les alcools sont des composés organiques qui sont parmi les plus reconnaissables et les plus familiers, car ils ont un large éventail d’applications et d’utilisations dans la vie quotidienne ...

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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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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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