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

Gli alcoli sono una classe di molecole organiche che possiedono almeno un gruppo funzionale ossidrile collegato a un atomo di carbonio. Il metanolo e l'etanolo sono due alcoli familiari. Entrambi sono alcoli alifatici, il che significa che derivano da un idrocarburo e non contengono un gruppo benzenico.
Esistono tre classificazioni di alcoli alifatici. Il primo è un alcol primario, in cui il gruppo ossidrile è collegato a un atomo di carbonio che è collegato a un gruppo a base di carbonio, o alchilico. In un alcol secondario, il gruppo ossidrile è collegato a un atomo di carbonio che ha due gruppi alchilici. Infine, in un alcol terziario, il gruppo ossidrile è collegato a un atomo di carbonio con tre gruppi alchilici.
Gli alcoli possono anche essere aromatici, in cui un gruppo ossidrile è collegato direttamente al carbonio di un anello benzenico. La forma più semplice di alcol aromatico è il fenolo. I composti che contengono fenolo sono noti come derivati del fenolo o fenoli.
Alcune reazioni subite dagli alcoli possono essere utilizzate per distinguerle in base a differenze visibili nell'esito della reazione. Una di queste reazioni è il test del cloruro ferrico, che verifica la presenza di fenoli. Quando il cloruro ferrico viene aggiunto a un fenolo, si forma un complesso di ferro e tre fenoli viola. Questo non si osserva quando viene aggiunto a un alcol alifatico.
Un'altra reazione utile è il test di Jones, che viene utilizzato per identificare gli alcoli alifatici primari e secondari. Il reagente di Jones, una miscela di acido solforico e triossido di cromo in acqua, è un forte agente ossidante. Reagisce con gli alcoli primari per formare aldeidi, che poi formano acidi carbossilici, e reagisce con gli alcoli secondari per formare chetoni. L'aggiunta del reagente di Jones agli alcoli primari e secondari fa sì che la soluzione cambi colore da arancione a verde scuro. Gli alcoli terziari non reagiscono con il reagente di Jones perché sono resistenti all'ossidazione.
Infine, possiamo distinguere gli alcoli alifatici con il test di Lucas. Il reagente di Lucas, che è una miscela di cloruro di zinco e acido cloridrico, reagisce con alcoli secondari e terziari attraverso una reazione di sostituzione nucleofila SN1. Il cloruro di zinco si coordina con l'ossigeno ossidrile per generare un eccellente gruppo uscente. Una volta eliminato, rimane un carbocatione caricato positivamente. Quindi, uno ione cloro attacca il carbocatione per formare un cloruro alchilico, che è insolubile in acqua e appare torbido.
Gli alcoli terziari reagiscono immediatamente con il reagente di Lucas per formare uno strato oleoso a temperatura ambiente. Gli alcoli secondari danno un risultato positivo dopo pochi secondi o pochi minuti. Gli alcoli primari danno un risultato negativo a meno che non vengano riscaldati.
In questo laboratorio, utilizzerai il test del cloruro ferrico, il test di Jones e il test di Lucas per identificare un alcol sconosciuto.

identificazione degli alcoli

<h4>alcoli</h4>
Gli alcoli sono composti organici tra i più riconoscibili e familiari, in quanto hanno applicazioni e usi ad ampio raggio nella vita di tutti i giorni. Gli alcoli sono molecole organiche contenenti un gruppo funzionale ossidrilico collegato a un gruppo alchilico o arilico (ROH). Se il carbonio ossidrile ha un solo gruppo R, è noto come alcol primario. Se ha due gruppi R, è un alcol secondario e se ha tre gruppi R, è un alcol terziario. Come molti altri composti organici, anche gli alcoli possono essere aromatici contenendo un anello benzenico. L'alcol aromatico più semplice è il fenolo.
L'identificazione di un alcol in chimica organica può essere ottenuta sfruttando le diverse proprietà dei tipi di alcoli. Sebbene sia possibile utilizzare vari metodi di analisi della strumentazione, come la risonanza magnetica nucleare (NMR), è possibile utilizzare anche altri test qualitativi. Accoppiando questi test, l'identità di un alcol può essere determinata in modo simile al modo in cui possono essere identificati aldeidi e chetoni.
<h4>Test del cloruro ferrico</h4>
Un metodo per distinguere tra un alcol alifatico e un alcol aromatico è l'uso del cloruro di ferro (III). Il composto di cloruro di ferro conferisce alla soluzione un aspetto rosso-arancio. In presenza di un alcol aromatico, come il fenolo, gli atomi di cloruro vengono sostituiti dall'alcol aromatico, modificando la proprietà di coordinazione dell'atomo di ferro centrale. Questo cambia il colore della soluzione in un colore viola. Gli alcoli alifatici non reagiscono con il cloruro di ferro (III) e, quindi, la soluzione rimane rosso-arancio.
<h4>Test di Jones</h4>
Il test di Jones utilizza il triossido di cromo in presenza di acido solforico per agire come un potente agente ossidante. In presenza del reagente di Jones, un alcol primario viene prima convertito in un'aldeide e poi in un acido carbossilico, mentre un alcol secondario viene ossidato in un chetone. Lo stato di ossidazione del cromo è la chiave di questo test. Il cromo è nello stato di ossidazione +6 nel reagente di Jones. I complessi di Cr(VI) nel reagente gli conferiscono il suo colore rossastro e arancione brillante.
Nel processo della reazione, il cromo viene ridotto da Cr(VI) allo stato di ossidazione +3 - Cr(III). Innanzitutto, l'alcol e l'acido cromico formano un estere cromato. Quindi, una base (H2O) scinde il legame C-H dell'alcol, formando il gruppo carbonilico mentre riduce Cr(VI) a Cr(IV). Il carbonio dell'alcol subisce un'ossidazione a 2 elettroni e il Cr(IV) subisce una riduzione a 2 elettroni, quindi questa è una fase di riduzione-ossidazione.
Il Cr(IV) partecipa a ulteriori fasi di ossidazione e viene infine ridotto a Cr(III). Il Cr(III) è spesso presente come ioni esaacquacromo(III) — [Cr(H2O)6]3+ — e complessi Cr(III), dove le molecole di H2O sono sostituite da uno o più ioni solfato — [Cr(H2O)5(SO4)]+. Questi complessi conferiscono al Cr(III) il caratteristico colore verde.
Gli alcoli terziari non reagiscono con il cromo e quindi non viene prodotto alcun precipitato, mantenendo la soluzione arancione. Pertanto, il test di Jones può aiutare a differenziare gli alcoli primari e secondari dagli alcoli terziari.
<h4>Test di Lucas</h4>
Il test di Lucas utilizza il cloruro di zinco (II) in presenza di acido cloridrico come reagente. In presenza di un alcol, il reagente Lucas alogena l'alcol, formando un prodotto insolubile in soluzioni acquose. La velocità di reazione per questo dipende fortemente dalla formazione di un carbocatione causata dalla perdita dell'ossidrile sotto forma di acqua. Un carbocatione formato da un alcol primario è instabile e quindi non si verificherà facilmente. Ciò si traduce in nessuna reazione osservabile a temperatura ambiente. Un alcol terziario formerà un carbocatione stabile, determinando una reazione rapida all'aggiunta del reagente Lucas. Ciò si traduce in una seconda fase che appare nella miscela di reazione perché il prodotto alogenato finale è insolubile in acqua. Gli alcoli secondari formeranno un carbocatione meno stabile rispetto agli alcoli terziari, ma la reazione avverrà a temperatura ambiente in pochi minuti. Pertanto, il test di Lucas può aiutare a distinguere tra alcoli primari, secondari e terziari.
<h4>referenze</h4>
<ol>
	<li style="font-size:17px">Streitwieser, A., Heathcock, C.H., Kosower, E.M. (1998). Introduzione alla Chimica Organica. Upper Saddle River, NJ: Prentice Hall.</li>
</ol>

Identificazione degli alcoli

Alcoli
Gli alcoli sono composti organici tra i più riconoscibili e familiari, in quanto hanno applicazioni e usi ad ampio raggio ...

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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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Video completi e incentrati sul curriculum sia per gli istruttori che per gli studenti nei corsi di laboratorio di Chimica introduttiva.

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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

Preparati a insegnare Identificazione degli alcoli con questa guida per istruttori di 7 minuti. Copre i passaggi chiave di preparazione per il laboratorio Chemistry su JoVE Lab Manual.

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Segui le procedure passo dopo passo di Identificazione degli alcoli in questo video di protocollo studente di 12 minuti. Parte della collezione Chemistry su JoVE Lab Manual.

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SC.912.P.8.1

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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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