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This requires a slightly advanced knowledge of acid base theory. To answer this question, I'll be going with the Bronsted-Lowry acid-base theory.

Remember, there are two factors to consider when determining acid strength - the ease with which a hydrogen atom leaves the molecule and the stability of the ions being formed.

In both cases, the hydrogen is attached to an oxygen, which, being electronegative, will attract the electrons from the hydrogen atom. This makes the hydrogen positively charged, which will allow it to be attracted to lone pairs on some other molecule. Therefore, since the bonds being broken are identical, let us examine the stability of the ions being formed.

In phenol, the oxygen (which was formerly attached to the lone pair), will now have a charge of -1. Electron delocalization now takes place - the new lone pair on the oxygen will overlap with the p-orbitals on the benzene ring. As a result, the negative charge is no longer entirely localized on the oxygen, but is spread around the whole ion. HOWEVER, the oxygen is still by far the most electronegative thing on the ion (carbons and hydrogens aren't really too keen to steal electrons ...). Thus, the delocalized electrons will still be heavily distorted towards it, leaving the oxygen with a negative charge ... which will, as you can imagine, attract the positive hydrogen ion towards it.

On the other hand, when a carboxylic acid loses an electron, the negative charge will distribute itself evenly between the two oxygens in the carboxylic group (which are, of course, equally electronegative). If you're wondering why, it's again because of electron delocalization and the overlap of the orbitals containing the lone pairs on the oxygen atoms. Don't confuse this with pi bonds and the overlap of p-orbitals - it is not the same thing. Anyway, since the charge is more spread out, the oxygen from which the hydrogen left is going to less attractive to hydrogen ions ... and so the bond is less likely to reform.

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Q: Why phenol is less acidic than carboxylic acid?
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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.


What is the difference between phenol and carboxylic acid?

The release of the H+ ion or (the proton) is much easier in the carboxylic acid as the Phenoxide ion is more electron dense than the Carboxy ion. this is because of to the lone pairs of electrons on the oxygen atom delocalising into the benzene pi ring activating the ring and making the phenoxide ion more electron dense make in it harder for it to donate a proton. on the coboxy ion the negative charge is Shared between the two oxygen's making it less electron dense. Making it easier for the carboxylic acid to donate a proton making it a stronger acid.


What is the acid part of an amino acid?

An acidic acid is something with a pH of less than 7.0. Actually this term is used for Amino acids having carboxylic groups higher than amino groups.


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.


Which is more acidic p-chloro phenol or p-fluoro phenol?

p-chloro phenol is more acidic thisi is because in p-fluoro phenol as fluorine and carbon have identical 2p orbitals, the overlapping is perfect Hence the +r effect and -I effect cancels thus making it less acidic

Related questions

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.


What is the difference between phenol and carboxylic acid?

The release of the H+ ion or (the proton) is much easier in the carboxylic acid as the Phenoxide ion is more electron dense than the Carboxy ion. this is because of to the lone pairs of electrons on the oxygen atom delocalising into the benzene pi ring activating the ring and making the phenoxide ion more electron dense make in it harder for it to donate a proton. on the coboxy ion the negative charge is Shared between the two oxygen's making it less electron dense. Making it easier for the carboxylic acid to donate a proton making it a stronger acid.


What is the acid part of an amino acid?

An acidic acid is something with a pH of less than 7.0. Actually this term is used for Amino acids having carboxylic groups higher than amino groups.


To make an organic molecule less acidic what functional groups should be added to the molecule in order to do so?

carboxylic acid and its derivatives


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.


Which is more acidic p-chloro phenol or p-fluoro phenol?

p-chloro phenol is more acidic thisi is because in p-fluoro phenol as fluorine and carbon have identical 2p orbitals, the overlapping is perfect Hence the +r effect and -I effect cancels thus making it less acidic


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


Does a base make an acid less acidic?

oo kasi ang base hindi acidic so less acidic na ung acid


Which is more acidic phenol or para-chloro phenol?

Phenol. Anisole doesn't have any acidic protons.


What is acid acidic?

acidic acid is the nucleic level found on sodas or cleaning products and do forth. its all acidic but the higher the acidic level is ITS LESS ACIDIC then lower number.


What is a slightly acidic pH?

An acid pH is anything less than 7 including zero.


If you add water to an acid will it weaken the acid?

Yes. It will dilute the acid and increase its pH value (less acidic).