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

Los alcoholes son una clase de moléculas orgánicas que poseen al menos un grupo funcional hidroxilo conectado a un átomo de carbono. El metanol y el etanol son dos alcoholes conocidos. Ambos son alcoholes alifáticos, lo que significa que se derivan de un hidrocarburo y no contienen un grupo benceno.
Hay tres clasificaciones de alcoholes alifáticos. El primero es un alcohol primario, donde el grupo hidroxilo está conectado a un átomo de carbono que a su vez está conectado a un grupo a base de carbono, o alquilo. En un alcohol secundario, el grupo hidroxilo está conectado a un átomo de carbono que tiene dos grupos alquilo. Finalmente, en un alcohol terciario, el grupo hidroxilo está conectado a un átomo de carbono con tres grupos alquilo.
Los alcoholes también pueden ser aromáticos, en los que un grupo hidroxilo está conectado directamente al carbono de un anillo de benceno. La forma más simple de un alcohol aromático es el fenol. Los compuestos que contienen fenol se conocen como derivados del fenol o fenoles.
Ciertas reacciones sufridas por los alcoholes se pueden utilizar para distinguirlos en función de las diferencias visibles en el resultado de la reacción. Una de estas reacciones es la prueba del cloruro férrico, que comprueba la presencia de fenoles. Cuando se agrega cloruro férrico a un fenol, se forma un complejo púrpura de hierro-tres-fenol. Esto no se observa cuando se añade a un alcohol alifático.
Otra reacción útil es la prueba de Jones, que se utiliza para identificar alcoholes alifáticos primarios y secundarios. El reactivo de Jones, una mezcla de ácido sulfúrico y trióxido de cromo en agua, es un fuerte agente oxidante. Reacciona con los alcoholes primarios para formar aldehídos, que a su vez forman ácidos carboxílicos, y reacciona con alcoholes secundarios para formar cetonas. La adición del reactivo de Jones a los alcoholes primarios y secundarios hace que la solución cambie de color de naranja a verde oscuro. Los alcoholes terciarios no reaccionan con el reactivo de Jones porque son resistentes a la oxidación.
Por último, podemos distinguir los alcoholes alifáticos con la prueba de Lucas. El reactivo de Lucas, que es una mezcla de cloruro de zinc y ácido clorhídrico, reacciona con alcoholes secundarios y terciarios a través de una reacción de sustitución nucleofílica SN1. El cloruro de zinc se coordina con el oxígeno hidroxilo para generar un excelente grupo de salida. Una vez eliminado, queda un carbocatión cargado positivamente. Luego, un ion de cloro ataca el carbocatión para formar un cloruro de alquilo, que es insoluble en agua y parece turbio.
Los alcoholes terciarios reaccionan inmediatamente con el reactivo de Lucas para formar una capa aceitosa a temperatura ambiente. Los alcoholes secundarios dan un resultado positivo después de unos segundos a unos minutos. Los alcoholes primarios dan un resultado negativo a menos que se calienten.
En este laboratorio, utilizará la prueba de cloruro férrico, la prueba de Jones y la prueba de Lucas para identificar un alcohol desconocido.

identificación de alcoholes

<h4>alcoholes</h4>
Los alcoholes son compuestos orgánicos que se encuentran entre los más reconocibles y familiares, ya que tienen una amplia gama de aplicaciones y usos en la vida cotidiana. Los alcoholes son moléculas orgánicas que contienen un grupo funcional hidroxilo conectado a un grupo alquilo o arilo (ROH). Si el carbono hidroxilo solo tiene un solo grupo R, se conoce como alcohol primario. Si tiene dos grupos R, es un alcohol secundario, y si tiene tres grupos R, es un alcohol terciario. Al igual que muchos otros compuestos orgánicos, los alcoholes también pueden ser aromáticos al contener un anillo de benceno. El alcohol aromático más simple es el fenol.
La identificación de un alcohol en química orgánica se puede lograr explotando las diferentes propiedades de los tipos de alcoholes. Si bien se pueden utilizar varios métodos de análisis de instrumentación, como la resonancia magnética nuclear (RMN), también se pueden utilizar otras pruebas cualitativas. Al acoplar estas pruebas, la identidad de un alcohol se puede determinar de manera similar a la forma en que se pueden identificar los aldehídos y las cetonas.
<h4>Prueba de cloruro férrico</h4>
Un método para diferenciar entre un alcohol alifático y un alcohol aromático es mediante el uso de cloruro de hierro (III). El compuesto de cloruro de hierro le da a la solución una apariencia de color rojo anaranjado. En presencia de un alcohol aromático, como el fenol, los átomos de cloruro son reemplazados por el alcohol aromático, cambiando la propiedad de coordinación del átomo de hierro central. Esto cambia el color de la solución a un color púrpura. Los alcoholes alifáticos no reaccionarán con el cloruro de hierro (III) y, por lo tanto, la solución permanece de color rojo anaranjado.
<h4>Prueba de Jones</h4>
La prueba de Jones utiliza trióxido de cromo en presencia de ácido sulfúrico para actuar como un poderoso agente oxidante. En presencia del reactivo de Jones, un alcohol primario se convierte primero en un aldehído y luego en un ácido carboxílico, mientras que un alcohol secundario se oxidará en una cetona. El estado de oxidación del cromo es la clave de esta prueba. El cromo se encuentra en el estado de oxidación +6 en el reactivo de Jones. Los complejos Cr(VI) en el reactivo le dan su color rojizo brillante y anaranjado.
En el proceso de la reacción, el cromo se reduce de Cr (VI) al estado de oxidación +3 — Cr (III). Primero, el alcohol y el ácido crómico forman un éster de cromato. Luego, una base (H2O) rompe el enlace C-H del alcohol, formando el grupo carbonilo mientras reduce Cr (VI) a Cr (IV). El carbono del alcohol se somete a una oxidación de 2 electrones y el Cr (IV) se somete a una reducción de 2 electrones, por lo que se trata de un paso de reducción-oxidación.
El Cr(IV) participa en las siguientes etapas de oxidación y finalmente se reduce a Cr(III). El Cr(III) suele estar presente en forma de iones hexaaquacromo(III) — [Cr(H2O)6]3+ — y complejos Cr(III), donde las moléculas de H2O son reemplazadas por uno o más iones sulfato — [Cr(H2O)5(SO4)]+. Estos complejos le dan al Cr(III) el característico color verde.
Los alcoholes terciarios no reaccionan con el cromo y, por lo tanto, no se produce precipitado, lo que mantiene la solución naranja. Por lo tanto, la prueba de Jones puede ayudar a diferenciar los alcoholes primarios y secundarios de los alcoholes terciarios.
<h4>Prueba de Lucas</h4>
La prueba de Lucas utiliza cloruro de zinc (II) en presencia de ácido clorhídrico como reactivo. En presencia de un alcohol, el reactivo de Lucas halogenará el alcohol, creando un producto insoluble en soluciones acuosas. La velocidad de reacción para esto depende en gran medida de la formación de un carbocatión causado por la pérdida del hidroxilo en forma de agua. Un carbocatión formado por un alcohol primario es inestable y, por lo tanto, no se producirá fácilmente. Esto da como resultado que no se observe ninguna reacción a temperatura ambiente. Un alcohol terciario formará un carbocatión estable, lo que dará lugar a una reacción rápida tras la adición del reactivo de Lucas. Esto da lugar a la aparición de una segunda fase en la mezcla de reacción porque el producto halogenado final es insoluble en agua. Los alcoholes secundarios formarán un carbocatión menos estable que los alcoholes terciarios, pero la reacción se producirá a temperatura ambiente en cuestión de minutos. Por lo tanto, la prueba de Lucas puede ayudar a diferenciar entre alcoholes primarios, secundarios y terciarios.
<h4>Referencias</h4>
<ol>
	<li style="font-size:17px">Streitwieser, A., Heathcock, C.H., Kosower, E.M. (1998). Introducción a la Química Orgánica. Upper Saddle River, Nueva Jersey: Prentice Hall.</li>
</ol>

Identificación de alcoholes

Alcoholes
Los alcoholes son compuestos orgánicos que se encuentran entre los más reconocibles y familiares, ya que tienen una amplia gama de aplicaciones y usos en la vida cotidiana ...

Education

Educación

JoVE Lab Manual

Chemistry

Química

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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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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