Name: why phenols are more acidic than alcohols
Uploaded: 2025-05-22T09:05:35.000Z
Duration: 2 min 36 s
Channel: JoVE

While the neutral forms of alcohols and phenols are amphoteric in nature, their corresponding anions form weak bases.
The oxygen atom of an alcohol polarizes both its adjacent bonds. While the polarization of the O&#8211;H bond makes alcohol a weak acid, the lone pairs on oxygen make it both basic and nucleophilic. 
The conjugate base of an aliphatic alcohol is an alkoxide ion, and that of a phenol is a phenoxide or phenolate ion. A negative charge is more stable on an oxygen atom than on nitrogen or carbon but most stable on a halogen atom. 
Recall that conjugate base stability is a measure of acidity. Therefore, alcohols are more acidic than terminal alkynes, amines, and alkanes but less acidic than hydrogen halides. 
Typical alcohols like methanol or ethanol are almost as acidic and basic as water. However, phenols are more acidic than alcohols but less acidic than carboxylic acids. Unlike alkoxide ions, the negative charge on the oxygen atom of phenoxide is stabilized by resonance and polarization via its aromatic ring.
Therefore, phenols can be deprotonated by a relatively weak base like hydroxide. However, alcohols can only be deprotonated by stronger bases like sodium metal or potass

acidity and basicity of alcohols and phenols

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O&#8211;H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water&#8212;a good one. The two acid&#8211;base equilibria corresponding to ethanol are depicted below.
<img alt="Chemical equilibrium diagram with radicals, showing ethanol and hydroxyl radicals; pKa values given." src="/files/ftp_upload/11922/11922_PT_Figure_1.svg" style="text-align: center; height: 50px;" data-altupdatedat="1754904545000" data-alt="Acid-base equilibrium, EtO&#8315; + HO&#183; &#8652; EtOH + O&#183;H&#8315;, chemical formula, pKa values: 15.9, 15.7." />
Figure 1. Loss of proton
<img alt="Acid-base reaction equation, equilibrium diagram, pKa values, organic chemistry concept." src="/files/ftp_upload/11922/11922_PT_Figure_2.svg" style="text-align: center; height: 70px;" data-altupdatedat="1754904545000" data-alt="Acid-base reaction mechanism, chemical equation diagram with pKa values, equilibrium process." />
Figure 2. Gain of proton
Methanol (pKa = 15.5) is the only alcohol that is slightly stronger than water (pKa = 15.7). Ethanol (pKa = 15.9), tert-butanol (pKa = 18.0), and others are weaker acids. However, all alcohols are stronger acids than terminal alkynes, and they are much stronger than hydrogen, ammonia, and alkanes.
<img alt="Chemical reaction sequence showing transformation of H2O to RH with intermediates, formula diagram." src="/files/ftp_upload/11922/11922_PT_Figure_3.svg" style="text-align: center; height: 22px;" data-altupdatedat="1754904545000" data-alt="Chemical reaction pathway diagram, showcasing transformation from H&#8322;O to RH via ROH, R&#8801;H, H&#8322;, NH&#8323;." />
Figure 3. Relative acidity
Since alcohols are weaker acids than water, their conjugate base alkoxide ions are stronger bases than the hydroxide ion. Alcohol can be converted into metal alkoxide using strong bases such as sodium/potassium hydride or sodium/potassium metal, which react violently but controllably with alcohol. When the alkyl substitution is bulky, the alkoxide ion is not solvated enough due to the steric effect, leading to less stabilization. Additionally, destabilization is favored by inductive effects. Consequently, the equilibrium lies predominantly towards alcohol.
Alcohols can also act as a base and accept protons from strong acids. Notably, conjugate bases of compounds with higher pKa than an alcohol will deprotonate that alcohol.
<img alt="Radical reactions pathway; chemical reaction sequence diagram; NH&#8322; to HO&#8315; transformation." src="/files/ftp_upload/11922/11922_PT_Figure_4.svg" style="text-align: center; height: 30px;" data-altupdatedat="1754904545000" data-alt="Free radical reaction pathway diagram showing stepwise chemical transformations." />
Figure 4. Relative basicity
Phenols are more acidic than alcohols. The conjugate base of a phenol is a phenoxide or phenolate ion. Resonance stabilization of the phenoxide ion coupled with the polar effect of the benzene ring enhances the acidity of phenols by eight orders of magnitude (100,000,000 times) over cyclohexanol. Therefore, phenol does not need to be deprotonated with a base as strong as sodium hydride. Instead, it can be deprotonated by hydroxide, unlike an alcohol.
Although phenol is a million-fold higher in acidity than ethanol, it is a hundred thousand-fold less acidic than acetic acid. Their relative acid&#8211;base properties can be used to separate each other from a mixture. When an ether solution of a mixture of alcohol and phenol is extracted with dilute sodium hydroxide, phenol gets completely partitioned into the aqueous phase as its sodium salt, while alcohol stays in the ether layer. On the other hand, dilute sodium bicarbonate is used to extract phenol and carboxylic acid from an ether solution of their mixture. Carboxylic acid gets quantitatively converted into its sodium salt and gets extracted from water while phenol remains in the ether phase.
<img alt="Acid-base equilibrium formulas in chemical reactions; diagram with equilibrium constants K&#62;1, K&#60;1." src="/files/ftp_upload/11922/11922_PT_Figure_5.svg" style="text-align: center; height: 170px;" data-altupdatedat="1754904545000" data-alt="Acid-base reactions diagram; equations show equilibrium constant K and strength of acids/bases." />
Figure 5. Acid&#8211;base equilibria of phenol
A phenoxide ion can be stabilized by delocalization of the oxygen's negative charge on the benzene ring. This is reinforced by electron-withdrawing functional groups like nitro, halide, etc. A substantial change in acidity is noted in phenols with an electron-withdrawing substituent, like a nitro group. An ortho- or para-nitro group stabilizes the phenoxide ion by delocalizing the negative charge on its own oxygen atoms. On the other hand, a meta-nitro group, being not directly conjugated to the phenoxide oxygen, stabilizes the phenolate ion to a lesser extent. Therefore, m-nitrophenol (pKa = 8.4) is more acidic than phenol but less acidic than o- or p-nitrophenol (pKa = 7.2). This also explains the extremely high acidity of 2,4-&#8288;dinitrophenol (pKa = 4.0) and 2,4,6-trinitrophenol (pKa = 0.4).
Table 1. The acidity constants (pKa) of acids (blue) and their conjugate bases.
<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;">Compound</td>
			<td style="color: black; border: 1px solid black; text-align: center;">Acid</td>
			<td style="color: black; border: 1px solid black; text-align: center;">Conjugate base</td>
			<td style="color: black; border: 1px solid black; text-align: center;">pKa</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Hydrogen chloride</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="HCl molecular structure, chemical bond diagram, illustrating hydrogen-chlorine bonding." src="/files/ftp_upload/11922/11922_PT_Figure_6.svg" style="text-align: center; height: 18px;" data-altupdatedat="1754904545000" data-alt="Hydrochloric acid molecule diagram H-Cl single bond, covalent structure, chemistry education." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chloride ion symbol Cl&#8315;, representing anions in chemical formulas and reactions." src="/files/ftp_upload/11922/11922_PT_Figure_7.svg" style="text-align: center; height: 18px;" data-altupdatedat="1754904545000" data-alt="Static equilibrium diagram; &#931;Fx=0, demonstrating force balance, vector components." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">&#8722;6.30</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Nitrophenol</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure of nitrophenol; aromatic ring, OH group, NO2 substituent; structural formula." src="/files/ftp_upload/11922/11922_PT_Figure_8.svg" style="text-align: center; height: 130px;" data-altupdatedat="1754904545000" data-alt="Chemical structure of para-nitrophenol molecule, formula diagram for organic chemistry study." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure of 4-nitrophenolate ion, formula diagram, used in organic chemistry studies." src="/files/ftp_upload/11922/11922_PT_Figure_9.svg" style="text-align: center; height: 130px;" data-altupdatedat="1754904545000" data-alt="Structure of p-nitrophenolate ion, chemical formula diagram, aromatic compound, organic chemistry." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">7.07</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Phenol</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Phenol chemical structure formula; aromatic molecule diagram, hydroxyl group, benzene ring." src="/files/ftp_upload/11922/11922_PT_Figure_10.svg" style="text-align: center; height: 90px;" data-altupdatedat="1754904545000" data-alt="Phenol structure diagram with hydroxyl group attached to benzene ring." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Phenoxide ion structure; aromatic ring, O with negative charge, chemical diagram, molecular chemistry." src="/files/ftp_upload/11922/11922_PT_Figure_11.svg" style="text-align: center; height: 90px;" data-altupdatedat="1754904545000" data-alt="Phenoxide ion structure; aromatic compound with negative oxygen; chemical diagram; organic chemistry." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">9.89</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">m-Cresol</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure, para-cresol, compound diagram, molecular formula C7H8O, hydroxyl and methyl groups." src="/files/ftp_upload/11922/11922_PT_Figure_12.svg" style="text-align: center; height: 90px;" data-altupdatedat="1754904545000" data-alt="Chemical structure of cresol formula; aromatic ring with OH and CH3 groups; organic chemistry." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure of cresolate ion, aromatic ring, structural formula for educational analysis." src="/files/ftp_upload/11922/11922_PT_Figure_13.svg" style="text-align: center; height: 90px;" data-altupdatedat="1754904545000" data-alt="Chemical structure of para-cresol ion, shown as chemical formula diagram for organic chemistry." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">10.1</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">2,2,2-Trifluoroethanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Organic chemistry, 2,2,2-trifluoroethanol structure, molecular diagram, alcohol functional group." src="/files/ftp_upload/11922/11922_PT_Figure_14.svg" style="text-align: center; height: 60px;" data-altupdatedat="1754904545000" data-alt="Chemical structure of 2,2,2-trifluoroethanol, molecular formula: C2H3F3O, structural diagram." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Chemical structure diagram of trifluoromethoxide anion (CF3O&#8722;), organic chemistry concept." src="/files/ftp_upload/11922/11922_PT_Figure_15.svg" style="text-align: center; height: 60px;" data-altupdatedat="1754904545000" data-alt="Alt text: Chemical structure of trifluoromethoxide ion, showing molecular formula COF3." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">12.0</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Water</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Water molecule structure, H2O, ball-and-stick diagram, chemistry, molecular model." src="/files/ftp_upload/11922/11922_PT_Figure_16.svg" style="text-align: center; height: 30px;" data-altupdatedat="1754904545000" data-alt="Water molecule structure, H2O, diagram showing atomic bonds and angles in chemistry." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Hydroxide ion chemical structure, formula H-O^-, molecular chemistry diagram." src="/files/ftp_upload/11922/11922_PT_Figure_17.svg" style="text-align: center; height: 18px;" data-altupdatedat="1754904545000" data-alt="Hydroxide ion chemical structure, formula illustration, educational chemistry diagram." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">15.7</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Ethanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Ethanol chemical structure, OH functional group, molecular diagram, organic chemistry." src="/files/ftp_upload/11922/11922_PT_Figure_18.svg" style="text-align: center; height: 25px;" data-altupdatedat="1754904545000" data-alt="Ethanol molecule structure; chemical formula C2H5OH; organic compound diagram." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Ether structural formula, chemical compound diagram, oxygen anion representation." src="/files/ftp_upload/11922/11922_PT_Figure_19.svg" style="text-align: center; height: 25px;" data-altupdatedat="1754904545000" data-alt="Ethoxide ion chemical structure, showing anionic oxygen in molecular formula." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">15.9</td>
		</tr>
		<tr>
			<td style="color: black; border: 1px solid black; text-align: center;">Cyclohexanol</td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Cyclohexanol structure, molecular formula C6H12O, hydroxyl group attached to cyclohexane ring." src="/files/ftp_upload/11922/11922_PT_Figure_20.svg" style="text-align: center; height: 90px;" data-altupdatedat="1754904545000" data-alt="Cyclohexanol chemical structure; hexagonal ring with OH group diagram for organic chemistry analysis." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;"><img alt="Cyclohexanone molecular structure, chemical diagram for organic chemistry visualization." src="/files/ftp_upload/11922/11922_PT_Figure_21.svg" style="text-align: center; height: 90px;" data-altupdatedat="1754904545000" data-alt="Cyclohexanone molecular structure; chemical formula diagram; organic chemistry educational use." /></td>
			<td style="color: black; border: 1px solid black; text-align: center;">16.0</td>
		</tr>
	</tbody>
</table>

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O&#8211;H bond making the hydrogen partially positive. ...

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

Education

JoVE Core

Organic Chemistry

Unit 1

Alcohols and Phenols

KEY TERMS AND CONCEPTS

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 acids than methanol. Even so, alcohols are still more acidic than terminal alkynes, and they are much more acidic than hydrogen, ammonia, and alkanes.

Because alcohols are weaker acids than water, their conjugate bases, called alkoxide ions, are stronger bases than hydroxide. Alcohols can be converted into metal alkoxides using strong bases such as sodium hydride or potassium hydride, or with sodium or potassium metal. These reactions can be violent but still controlled. Bulky alkyl groups can also make the alkoxide less stabilized because of steric effects and inductive effects, so the equilibrium stays mostly on the alcohol side.

Alcohols can also act as bases. They accept protons from strong acids. In general, conjugate bases of compounds with a higher pKa than an alcohol can deprotonate that alcohol. This is why alcohols take part in both acid-base directions, depending on the partner.

Phenols are more acidic than alcohols. Their conjugate base is the phenoxide, or phenolate, ion. Resonance spreads out the negative charge over the benzene ring, and the benzene ring also has a polar effect. Together, these effects make phenols about 100,000,000 times more acidic than cyclohexanol. Phenol can therefore be deprotonated by hydroxide, unlike most alcohols.

Phenol is still much less acidic than acetic acid, even though it is about a million times more acidic than ethanol. This difference can be used to separate mixtures. In an ether solution, dilute sodium hydroxide pulls phenol into the aqueous layer as its sodium salt, while the alcohol remains in the ether layer. Dilute sodium bicarbonate can separate phenol from a carboxylic acid mixture as well. The carboxylic acid becomes its sodium salt and moves into water, while phenol stays in the ether phase.

The acidity of phenols changes when electron-withdrawing groups are added. Nitro groups, halides, and similar groups help stabilize the phenoxide ion. An ortho- or para-nitro group can delocalize the negative charge through the ring and onto its own oxygen atoms, so these phenols are more acidic. A meta-nitro group is less effective because it is not directly conjugated with the phenoxide oxygen.

This pattern explains the pKa values of nitrophenols. m-Nitrophenol has a pKa of 8.4, so it is more acidic than phenol but less acidic than o- or p-nitrophenol, which have a pKa of 7.2. The same effect makes 2,4-dinitrophenol very acidic, with a pKa of 4.0, and 2,4,6-trinitrophenol even stronger, with a pKa of 0.4. These examples show how structure can shift the acid-base behavior of phenols.

Why Phenols Are More Acidic Than Alcohols

why-phenols-are-more-acidic-than-alcohols

structure and nomenclature of alcohols and phenols

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

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...

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 why phenols are more acidic than alcohols, how alkoxides form, and how pKa values and resonance explain acid-base separation and reactivity.

Why Phenols Are More Acidic Than Alcohols | JoVE K12

organic chemistry

JoVE Core Organic Chemistry explains basic concepts of stereochemistry, reactions, and mechanisms using concise and easy-to-understand animated video lessons. Additionally, the scientist-in-action videos demonstrate the application of related concepts in classical and original research experiments performed in today's laboratories worldwide.

Why Phenols Are More Acidic Than Alcohols

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