Name: alcohols and phenols: naming basics
Uploaded: 2023-04-30T18:28:39.000Z
Duration: 2 min 23 s
Channel: JoVE

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Physical Science

Matter and its Interactions

PS.PSc.2.2

structure-and-nomenclature-of-alcohols-and-phenols

Structure and Nomenclature of Alcohols and Phenols

Alcohols, represented by the general formula CnH2n+1OH, are organic compounds with a hydroxy group attached to an sp3-hybridized carbon of an aliphatic system.
They exhibit a bent geometry around the oxygen atom, where the sp3 hybrid orbital of oxygen overlaps with the sp3 hybrid orbital of carbon, forming a sigma bond. The carbon&#8211;oxygen&#8211;hydrogen bond angle approximates the tetrahedral value of 109.5&#176;.
Alcohols are classified as primary, secondary, or tertiary depending on the number of carbon atoms attached to the carbon bearing the &#8211;OH group.
The common names for alcohols add &#39;alcohol&#39; to the name of the alkyl group attached to the hydroxy group.
The IUPAC names are derived from the name of the parent chain by replacing the final &#39;&#8211;e&#39; of the suffix with &#39;&#8211;ol&#39;. The locant may be before either the parent name or the suffix.
When identifying and numbering the parent chain, the hydroxy group takes precedence, followed by pi bonds, chain length, and lower-priority substituents.
Cyclic alcohols add the prefix &#39;cyclo&#39; to the parent chain&#39;s name. The carbon bearing the &#8211;OH group is numbered as one.
When naming polyols, the final &#39;&#8211;e&#39; of the parent chain is retained, and multiplier prefix

structure and nomenclature of alcohols and phenols

<h4>Overview </h4>
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or &#8211;OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols are named by formal and standard systems. The most adopted system is the International Union of Pure and Applied Chemistry (IUPAC).
The IUPAC names of the alcohols are derived by adding the suffix 'ol' to the name of the parent alkane. Phenols, on the other hand, are named as hydroxy derivatives of benzene. 'Phenol' is used as the parent name rather than benzene.
Like all organic compounds, alcohols and phenols have several commercial applications. For instance, ethanol is the main ingredient in alcoholic beverages like wine or beer. Phenols are widely used as antiseptics and as disinfectants.
<h4>Naming Alcohols</h4>
The table below shows the classification and nomenclature of some alcohols and phenols.
<table style="margin-left: auto; margin-right: auto;">
	<tbody style="border: 1px solid black;">
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Skeletal Structures</td>
			<td style="color: black; border: 1px solid black; text-align: center;">IUPAC Name</td>
			<td style="color: black; border: 1px solid black; text-align: center;">Common Name</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure of 1-butanol, organic compound, structural formula, hydroxyl group." src="/files/ftp_upload/11920/Figure%201.svg" style="text-align: center; height: 27px;" data-altupdatedat="1761830439000" data-alt="Figure1" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">1-butanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">n-butyl alcohol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Isobutanol chemical structure diagram, illustrating molecular arrangement and OH functional group." src="/files/ftp_upload/11920/Figure%202.svg" style="text-align: center; height: 55px;" data-altupdatedat="1761830439000" data-alt="Figure2" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">2-butanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">sec-butyl alcohol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Structural formula, butanol isomer diagram; chemical notation for organic synthesis, hydrocarbon study." src="/files/ftp_upload/11920/Figure%203.svg" style="text-align: center; height: 70px;" data-altupdatedat="1761830439000" data-alt="Figure3" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">2-methyl-2-butanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">t-amyl alcohol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure diagram, cyclopentanol derivative with bromine, chlorine; organic chemistry." src="/files/ftp_upload/11920/Figure%204.svg" style="text-align: center; height: 70px;" data-altupdatedat="1761830439000" data-alt="Figure4" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">2-bromo-4-chlorocyclopentanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">-</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Structural formula of allyl alcohol, illustrating its molecular composition." src="/files/ftp_upload/11920/Figure%205.svg" style="text-align: center; height: 30px;" data-altupdatedat="1761830439000" data-alt="Figure5" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">2-propen-1-ol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">allyl alcohol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Phenol chemical structure, benzene ring with hydroxyl group, organic chemistry diagram." src="/files/ftp_upload/11920/Figure%206.svg" style="text-align: center; height: 50px;" data-altupdatedat="1761830439000" data-alt="Figure6" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">3-cyclohexen-1-ol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">-</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Ethylene glycol structural formula; diagram for chemical study and education." src="/files/ftp_upload/11920/Figure%207.svg" style="text-align: center; height: 30px;" data-altupdatedat="1761830439000" data-alt="Figure7" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">1,2-ethanediol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">ethylene glycol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Glycerol structural formula diagram; chemical structure, organic chemistry study, C3H8O3." src="/files/ftp_upload/11920/Figure%208.svg" style="text-align: center; height: 50px;" data-altupdatedat="1761830439000" data-alt="Figure8" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">1,2,3-propanetriol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">glycerol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Phenol molecular structure; chemical formula; aromatic ring with hydroxyl group; organic chemistry." src="/files/ftp_upload/11920/Figure%209.svg" style="text-align: center; height: 50px;" data-altupdatedat="1761830439000" data-alt="Figure9" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">phenol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">phenol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure of hydroquinone showing molecular formula, aromatic ring diagram, sample analysis." src="/files/ftp_upload/11920/Figure%2010.svg" style="text-align: center; height: 60px;" data-altupdatedat="1761830439000" data-alt="Figure10" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">benzene-1,3-diol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">resorcinol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Structural formula of para-cresol, illustrating aromatic organic compound with hydroxyl group." src="/files/ftp_upload/11920/Figure%2011.svg" style="text-align: center; height: 75px;" data-altupdatedat="1761830439000" data-alt="Figure11" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">2-methylphenol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">o-cresol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure of cresol molecule; aromatic compound formula; organic chemistry diagram." src="/files/ftp_upload/11920/Figure%2012.svg" style="text-align: center; height: 60px;" data-altupdatedat="1761830439000" data-alt="Figure12" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">3-methylphenol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">m-cresol</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure diagram of para-cresol, aromatic compound with CH3 and OH groups on benzene ring." src="/files/ftp_upload/11920/Figure%2013.svg" style="text-align: center; height: 50px;" data-altupdatedat="1761830439000" data-alt="Figure13" /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">4-methylphenol</td>
			<td style="color: black; border: 1px solid black; text-align: center;">p-cresol</td>
		</tr>
	</tbody>
</table>

Overview 
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is ...

Education

JoVE Core

Organic Chemistry

Unit 1

Alcohols and Phenols

KEY TERMS AND CONCEPTS

alcohols and phenols: naming basics

Alcohols and phenols are important organic compounds with simple naming rules. Alcohols contain a hydroxyl group, or –OH group, directly bonded to carbon. Phenols also contain an OH group, but it is attached directly to a benzene ring.

Alcohols are usually colorless. Phenol is a white crystalline compound with a characteristic hospital smell. These compounds are named using formal and standard systems. The most widely used system is the International Union of Pure and Applied Chemistry, or IUPAC.

In IUPAC naming, alcohols are named from the parent alkane. The suffix &quot;ol&quot; is added to the alkane name. Phenols are named as hydroxy derivatives of benzene. In this system, &quot;phenol&quot; is used as the parent name instead of benzene.

These compounds also have practical uses. Ethanol is the main ingredient in alcoholic drinks such as wine and beer. Phenols are used as antiseptics and disinfectants. The examples in the table show both IUPAC names and common names, including 1-butanol, 2-butanol, 2-methyl-2-butanol, allyl alcohol, ethylene glycol, glycerol, phenol, resorcinol, and cresol isomers.

Alcohols and Phenols: Naming Basics

Alcohols and phenols are important organic compounds with simple naming rules. Alcohols contain a hydroxyl group, or –OH group, directly bonded to carbon. Phenols also contain an OH group, but it is attached directly to a benzene ring. Alcohols are usually colorless. Phenol is a white crystalline compound with a characteristic hospital smell. These compounds are named using formal and standard systems. The most widely used system is the International Union of Pure and Applied Chemistry, or...

physical properties of alcohols and phenols

physical-properties-of-alcohols-and-phenols

Alcohols and Phenols: Boiling Point Trends

Alcohols and phenols are organic compounds whose physical properties depend on structure. In alcohols, a hydroxy group is attached to a saturated carbon. In phenols, the hydroxy group is attached to an aromatic ring. Their boiling points and water solubility are shaped by hydrogen bonding and dispersion forces. The oxygen-hydrogen dipole in the hydroxy group allows intermolecular hydrogen bonding. This gives alcohols a higher boiling point than aliphatic hydrocarbons with similar molecular...

acidity and basicity of alcohols and phenols

acidity-and-basicity-of-alcohols-and-phenols

Why Phenols Are More Acidic Than Alcohols

Alcohols are weak acids and weak bases because the O–H bond is polar and the oxygen atom has lone pairs. The partially positive hydrogen can be lost as a proton, and the oxygen can also accept a proton. When an alcohol is protonated, hydroxide changes into water, which is a much better leaving group. Alcohols vary a little in acidity. Methanol, with a pKa of 15.5, is slightly stronger as an acid than water, which has a pKa of 15.7. Ethanol, tert-butanol, and many other alcohols are weaker...

preparation of alcohols via addition reactions

preparation-of-alcohols-via-addition-reactions

Alcohol Synthesis from Alkenes

Alcohol synthesis from alkenes can follow three addition reactions: acid-catalyzed hydration, oxymercuration-demercuration, and hydroboration-oxidation. These methods all add across the double bond, but they give different alcohol products from the same alkene. In acid-catalyzed hydration, water adds to the double bond in an acidic atmosphere. The acid lets the hydrogen in water act as an electrophile and attack the alkene. A proton first adds to the double bond and forms a carbocation, which...

acid-catalyzed dehydration of alcohols to alkenes

acid-catalyzed-dehydration-of-alcohols-to-alkenes

Alcohol Dehydration Pathways to Alkene Products

Alcohol dehydration forms alkenes and water by removing a hydroxyl group and a hydrogen from a neighboring carbon. This reaction is usually done by heating the alcohol with an acid catalyst. Primary alcohols need higher temperatures and stronger acid conditions, while secondary and tertiary alcohols can react under milder conditions. Secondary and tertiary alcohols usually dehydrate through an E1 mechanism. In the first fast step, the alcohol is protonated and becomes an alkyloxonium ion. Then...

alcohols from carbonyl compounds: reduction

alcohols-from-carbonyl-compounds-reduction

Making Alcohols by Carbonyl Reduction

Making alcohols by carbonyl reduction is a key reaction in organic chemistry. It converts a carbonyl group into a hydroxyl group. The main routes are catalytic hydrogenation, hydride reduction, and borane reduction. Catalytic hydrogenation works by adding H2 across the pi bond of the carbonyl group. It uses transition metal catalysts such as Raney Ni, Pd-C, Pt, or Ru. Aldehydes and ketones can be reduced this way under mild to moderate heat, usually 25–100°C, and H2 pressure of about 1–5 atm.

alcohols from carbonyl compounds: grignard reaction

alcohols-from-carbonyl-compounds-grignard-reaction

Grignard Reagents in Alcohol Synthesis

Grignard reagents are key tools for making alcohols from carbonyl compounds. They are organomagnesium halides with a highly polar carbon–magnesium bond. Because this bond is partly ionic, the carbon acts as a strong nucleophile. It attacks the carbonyl carbon, which is the electrophilic part of a carbonyl group. Magnesium in the reagent also helps the reaction move forward. It coordinates with the carbonyl oxygen and lowers the electron density on the carbonyl carbon. This makes the carbonyl...

protection of alcohols

Alcohol Protecting Groups in Synthesis

Alcohol protecting groups help control which part of an organic molecule reacts during synthesis. A protecting group is a masking agent that makes a more reactive species inert under a chosen set of conditions. The lesson uses a pipe-flow analogy to show how this improves reaction selectivity. It also shows how protecting an alcohol can allow an organolithium alkylation of a halide to occur when the alcohol would otherwise compete. Common protecting groups for alcohols include trialkylsilyl...

preparation of diols and pinacol rearrangement

preparation-of-diols-and-pinacol-rearrangement

Pinacol Rearrangement of Vicinal Diols

Vicinal diols are compounds with two hydroxyl groups on adjacent carbon atoms. They are also called glycols. Under acidic conditions, these diols can undergo a pinacol rearrangement. The reaction starts when the acid catalyst transfers a proton to one hydroxyl group. This forms an oxonium ion. The oxonium ion then loses water and creates a tertiary carbocation intermediate. Next, a methyl group migrates from one carbon to the neighboring carbon. This step forms a resonance-stabilized cation...

conversion of alcohols to alkyl halides

Alcohols to Halides: Reagents and Mechanisms

Alcohols can be turned into alkyl halides by using reagents that make the hydroxyl group a better leaving group. The hydroxyl group is first protonated, which helps the reaction move forward. From there, the pathway can follow either an SN1 or SN2 substitution, depending on the starting alcohol and the reaction conditions. Tertiary alcohols usually form tertiary alkyl halides through a two-step SN1 mechanism. This route goes through a carbocation intermediate, and hyperconjugation helps...

oxidation of alcohols

Alcohol Oxidation Reagents and Products

Alcohol oxidation changes primary and secondary alcohols into carbonyl compounds. The reaction can mean loss of electrons, loss of hydrogen, or addition of oxygen. Oxidation is the opposite of reduction, so carbonyls can be reduced to alcohols, and alcohols can be oxidized back to carbonyls. The product depends on the alcohol type and the hydrogens on the alpha-carbon, the carbon next to the hydroxyl group. Primary alcohols can become aldehydes and then carboxylic acids. Secondary alcohols can...

preparation of alcohols via substitution reactions

preparation-of-alcohols-via-substitution-reactions

Alcohol Formation from Alkyl Halides

Alcohols can be made from alkyl halides by nucleophilic substitution. In these reactions, the carbon-halogen bond is highly polar, so the halide can leave the molecule. A nucleophile such as hydroxide ion or water then replaces the halide and forms an alcohol. The reaction path depends on the alkyl halide. Primary alkyl halides usually form primary alcohols through the SN2 mechanism. In SN2, the nucleophile attacks the halogen-bearing carbon from the side opposite the carbon-halogen bond. With...

key terms and concepts

Learn how alcohols and phenols are identified and named with IUPAC rules, key structures, and real-world examples like ethanol and phenol.

Alcohols and Phenols: Naming Basics | JoVE K12

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Alcohols and Phenols: Naming Basics

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