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Phenol does not undergo nucleophilic substitution for several reasons: phenol is a relatively stable compound, OH on its own is not one of the best leaving groups, and the aromatic ring does provides an extremely high energy barrier which prevents the initiation of either the SN1 or SN2 substitution mechanisms under normal conditions. When looking at the keto-enol tautomerization resonance forms, the enolate is the major contributor due to the aromatic stabilization. In order to substitute in place of the phenol, the hydroxy group needs to be converted to a better leaving group such as a Toluenesulfonate ester. It is possible to acylate phenols to form other compounds such as aspirin (o-Acetylsalicylic acid). It is alos possible to form aryl ethers with phenols. Benzediols (quinones) can be readily oxidized, allowing even more chemistry to be done to the aromatic system.
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∙ 16y ago
Wiki User
∙ 14y agoPhenol is acidic in nature while alcohol does not, the electron pair of oxygen of phenol becomes involved in resonance so not available for the attack at carbonium ion of carboxylic acid formed with the help of sulphuric acid so esterification is not possible.
Wiki User
∙ 10y agoIn phenols the lone pair of electron of oxygen atom of 'OH' group becomes involved in process of resonance and a double bond like linkage is formed between oxygen and carbon atom so removal of 'OH' group becomes restricted and substitution is not possible.
Wiki User
∙ 13y agophenol is more electro negative than alcohol so its dissociation power is more than alcohol.
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Why phenol more acidic than aliphatic alcohol and water?
why phenol more than aliphatic alcohol and water
Is water more acidic than phenol?
No. Phenol is far more acidic than water.
Is 1-hexanol more acidic or less acidic than phenol?
1-hexanol is an alcohol so it is a neutral compound not an acid while phenol is a strong acid.
Phenol are acidic in nature but alcohol not yet?
Phenol is more acidic than alcohols since the negative charge that is acquired by removal of a hydrogen atom can be delocalised into the molecules ring structure. acyclic alcohols cannot "spread" this charge as well as conjugated systems and thus will less readily lose their hydrogen atom.
Which one have higher boiling point alcohol or phenol?
Phenol has a higher boiling point than alcohol does; it has a stronger dipole difference in its -OH group.
Why phenol more acidic than aliphatic alcohol and water?
why phenol more than aliphatic alcohol and water
Is water more acidic than phenol?
No. Phenol is far more acidic than water.
Is 1-hexanol more acidic or less acidic than phenol?
1-hexanol is an alcohol so it is a neutral compound not an acid while phenol is a strong acid.
Which is more acidic phenol or para-chloro phenol?
Phenol. Anisole doesn't have any acidic protons.
What the Difference between the alcohol and phenol?
Alcohol: C6H13OH (hydroxy-hexane) Phenol : C6H5OH (hydroxy-benzene) Phenolic -OH is acidic (4x stronger than vinegar) where s alcoholic -OH isn't acidic at all; both are NOT ionic or alkaline (OH-)
Why phenol is more acidic than ethanol?
phenol is more acidic because of the benzene ring present in the molecule,when you lose the H form the OH group it is possible to delocalise the charge around the aromatic system due to the pi electron cloud,straight chain alcohols cannot do this so it is less favourable to deprotonate them hance it is easier to deprotonate a phenol,hence we say it is more acidic
Why phenol more acidic than alcohols?
Acidity depends on the concentration of H+. Due to higher electronegativity of sp2 hybridised carbon of phenol, the electron density on the oxygen decreases and hence increases the polarity O-H making the phenol unstable compared to phenolate, so it is more acidic. The C6H5-group is a fully sp2-hybridised electron pulling group.If you have electron providing groups (sp3) in CH3-CH2-O-H, it may decrease the polarity of O-H bond and destabilize the negatively charged ethanoate group (CH3CH2O-)
Phenol are acidic in nature but alcohol not yet?
Phenol is more acidic than alcohols since the negative charge that is acquired by removal of a hydrogen atom can be delocalised into the molecules ring structure. acyclic alcohols cannot "spread" this charge as well as conjugated systems and thus will less readily lose their hydrogen atom.
Which one have higher boiling point alcohol or phenol?
Phenol has a higher boiling point than alcohol does; it has a stronger dipole difference in its -OH group.
Why are phenols acidic in nature?
Phenol can act as an acid due to it's stability as phenoxide ion. By releasing H+ ion it will form stable C6H5O- ion. The groups having +I, -I , +M , -M efffects present on phenol will effect acidic nature of phenol. As +I or +M groups which are present at ortho and at para psitions will decrease the acidic character of phenol. If they are at meta position effect is less than at para or ortho positions.Similar to this -I or -M gorups are substituted on phenol they will increase the acidic nature. so, we can say that as the stability of phenoxide ion increases acidic nature of phenol also increases.Phenol can act as an acid due to it's stability as phenoxide ion. By releasing H+ ion it will form stable C6H5O- ion. The groups having +I, -I , +M , -M efffects present on phenol will effect acidic nature of phenol. As +I or +M groups which are present at ortho and at para psitions will decrease the acidic character of phenol. If they are at meta position effect is less than at para or ortho positions.Similar to this -I or -M gorups are substituted on phenol they will increase the acidic nature. so, we can say that as the stability of phenoxide ion increases acidic nature of phenol also increases.Phenol is a weak acid because of the presence of the hydrogen ions.
Why is phenol more soluble in aqueous NaOH than in water?
Phenol is acidic in nature. The phenolate anion is stable through resonance. Hence, an acid base reaction ensues between phenol and NaOH in water resulting in the formation of sodium phenolate, which is highly soluble in water compared to phenol.
Why is the boiling point of phenol greater than alcohol?
This is because the intermolecular forces holding the molecules of phenol together are stronger than the intermolecular forces holding the molecules of alcohol together.
