Salicylic acid is a stronger acid than Benzoic acid. Why?

Salicylic acid is a stronger acid than benzoic acid. It is due to the fact that in salicylate ion (conjugate base of salicylic acid) intramolecular H-bond formation takes place which makes the conjugate base more stable.

Related Questions:

1.                 Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?

2.                 Benzamide is less easily hydrolysed than methyl benzoate. Why ?

3.                 Alcohols and Phenols both are acidic but phenols are more acidic. Why?

4.                 Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?

5.        Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?

6.                 What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?

7.                 Name of groups which does not show ortho effect in benzoic acid?

8.                 Why Picric acid (2,4,6-trinitrophenol) is weak acid then expected ?

9.                 What is Steric Inhibition of Deprotonation effect ? Or SID effect ?

10.           Alcohols and Phenols both are acidic but phenols are more acidic. Why?

11.           Among orthochlorophenol and orthofluorophenol, which will be a stronger acid and why?

12.           Why The phenoxide ion is more stable than phenol ?

13.           What is correct acidic strengths order of the haloforms acids ? Give correct explanation.

14.           Lower aliphatic acids having 1 to 5 carbons are soluble in water but higher fatty acids having six or more than six carbon are insoluble in water but soluble in alcohol. Explain.

15.           Phenoxide ion is more stable than an alkaoxide. why?

16.           Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?

Why 2,6-Dihydroxybenzoic acid is more acidic than 2-hydroxybenzoic acid followed by benzoic acid ?

Due to intramolecular hydrogen bonding of conjugate base of acid give extra stability to the conjugate base hence acidic strength increase for example salicylic acid (2-hydroxybenzoic acid) is more acidic than benzoic acid and 2,6-Dihydroxybenzoic acid is more acidic than  2-hydroxybenzoic acid.

Related Questions:

1. Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?
2. Benzamide is less easily hydrolysed than methyl benzoate. Why ?
3. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
4. Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?
5. Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?
6. What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?
7. Name of groups which does not show ortho effect in benzoic acid?
8. Why Picric acid (2,4,6-trinitrophenol) is weak acid then expected ?
9. What is Steric Inhibition of Deprotonation effect ? Or SID effect ?
10. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
11. Among orthochlorophenol and orthofluorophenol, which will be a stronger acid and why?
12. Why The phenoxide ion is more stable than phenol ?
13. What is correct acidic strengths order of the haloforms acids ? Give correct explanation.
14. Lower aliphatic acids having 1 to 5 carbons are soluble in water but higher fatty acids having six or more than six carbon are insoluble in water but soluble in alcohol. Explain.
15. Phenoxide ion is more stable than an alkaoxide. why?
16. Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?
17. Chloroform is more acidic than fluoroform why?
18. Fluorine is more electronegative than chlorine even then, p-flurobenzoic acid is weaker acid than p-chlorobenzoic acid explain ?

How to determine acidic strength order of following compounds?

1. Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?
2. Benzamide is less easily hydrolysed than methyl benzoate. Why ?
3. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
4. Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?
5. Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?
6. What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?
7. Name of groups which does not show ortho effect in benzoic acid?
8. Why Picric acid (2,4,6-trinitrophenol) is weak acid then expected ?
9. What is Steric Inhibition of Deprotonation effect ? Or SID effect ?
10. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
11. Among orthochlorophenol and orthofluorophenol, which will be a stronger acid and why?
12. Why The phenoxide ion is more stable than phenol ?
13. What is correct acidic strengths order of the haloforms acids ? Give correct explanation.
14. Lower aliphatic acids having 1 to 5 carbons are soluble in water but higher fatty acids having six or more than six carbon are insoluble in water but soluble in alcohol. Explain.
15. Phenoxide ion is more stable than an alkaoxide. why?
16. Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?
17. Chloroform is more acidic than fluoroform why?
18. Fluorine is more electronegative than chlorine even then, p-flurobenzoic acid is weaker acid than p-chlorobenzoic acid explain ?

Related Questions:

1. Penta-1,3-diene is more stable than penta-1,4 -diene. Why?
2. Phenoxide ion is more stable than an alkaoxide. why?
3. Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?
4. Why enol form of Beta Dicarbonyl compound more stable than those of monocarbonyl compounds?
5. Why enol form of phenol is more stable than its keto isomers?
6. Reactivity order of Pyrrole, Furan and Thiophene towards Electrophilic substitution :
7. Phenyl group is known to extract negative inductive effect, but each phenyl ring in biphenyl is more reactive than benzene towards Electrophilic substation. Why?
8. Chloroform is more acidic than fluoroform why?
9. Fluorine is more electronegative than chlorine even then, p-flurobenzoic acid is weaker acid than p-chlorobenzoic acid explain ? 
10. Trifluoroethyl carbocation is less stable than trifluromethyl carbocation why ?
11. Why is the Tropylium carbocation less stable than the tricyclopropylmethyl carbocation?

Alcohols and Phenols both are acidic but phenols are more acidic. Why?

(1)  alcohols fails to turn blue litmus red while phenol do so.

(2) alcohols fails to neutralize alkalies whereas phenols do so:

(3) Both phenol and phenoxide ions exhibit resonance, whereas alcohols and alkoxide ion do not.

(4) Due to resonance, positive charge 's developed over "O"of phenol, this weakens O-H bond and facilitates release of a proton. On the other hand. due to electron donating nature of alkyl group. -O-H bond is strengthened. therefore. it hinders the release of proton.      

(5) The phenoxide ion is more stable than phenol, due to o greater dispersal of  negative charge, therefore. equilibrium get shifted to forward direction. whereas alkoxide ion is less stable than alcohols due to intensification of negative charge, so equilibrium get shifted towards backward direcrion. Due to these fact it is clear that phenols are more acidic than alcohols. 

Related Questions:

(1) Benzamide is less easily hydrolysed than methyl benzoate. Why ?

(2) Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?

(3) Phenoxide ion is more stable than an alkaoxide. why?

(4) What is Steric Inhibition of Deprotonation effect ? Or SID effect ?

(5) What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?

(6) Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?

(7) Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?

What is Steric Inhibition of Deprotonation effect ? Or SID effect ?

We know that picric acid is weak acid than expected this is fact that when picric acid releases a proton it becomes an anion for which repulsion results between oxygen atoms of phenoxide ion and oxygen of nitrate group, commonly known as Steric Inhibition of Deprotonation (SID effect). This also results in slight unstability of phenoxide ion and also decrease acidity. Thus picric acid is a weak acid than expected ever.

Related Questions:

1. Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?
2. Benzamide is less easily hydrolysed than methyl benzoate. Why ?
3. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
4. Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?
5. Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?
6. What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?
7. Name of groups which does not show ortho effect in benzoic acid?
8. Why Picric acid (2,4,6-trinitrophenol) is weak acid then expected ?
9. What is Steric Inhibition of Deprotonation effect ? Or SID effect ?
10. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
11. Among orthochlorophenol and orthofluorophenol, which will be a stronger acid and why?
12. Why The phenoxide ion is more stable than phenol ?
13. What is correct acidic strengths order of the haloforms acids ? Give correct explanation.
14. Lower aliphatic acids having 1 to 5 carbons are soluble in water but higher fatty acids having six or more than six carbon are insoluble in water but soluble in alcohol. Explain.
15. Phenoxide ion is more stable than an alkaoxide. why?
16. Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?
17. Chloroform is more acidic than fluoroform why?
18. Fluorine is more electronegative than chlorine even then, p-flurobenzoic acid is weaker acid than p-chlorobenzoic acid explain ?

Why Picric acid (2,4,6-trinitrophenol) is weak acid then expected ?

Picric acid is weak acid than expected due to the presence of three Nitro groups (show strong -I as well as -M effect); this is fact that  6-membered cyclic H-bonding takes place between H of -OH and O atoms of -NO2 groups which lower acidity significantly than the expected acidity.

And second fact that when picric acid releases a proton it becomes an anion for which repulsion results between oxygen atoms of phenoxide ion and oxygen of nitrate group, commonly known as Steric Inhibition of Deprotonation (SID effect). This also results in slight unstability of phenoxide ion and also decrease acidity. Thus picric acid is a weak acid than expected ever.

Name of groups which does not show ortho effect in benzoic acid?

Mostly groups are show Ortho effect, however for groups like -NH₂ or -OH does not experience SIR effect due to small size and –CN is linear group so SIR effect not applicable.

What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?

Ortho substituted Benzoic acid is more acidic then meta or para substituted benzoic acid irrespective of nature of group (electron donating group or electron withdrawing group) 

When a group present in the ortho position with respect to carboxylic group creates steric strain resulting in rotation of the carboxylic group and shifting it out of plane of the benzene ring as a resultthe carboxylic group can no longer participate in ring resonance and thereby the acidity increases as delocalization of negative charge equally on the both oxygen atom of  conjugate base ( carboxylate ion) of the benzoic acid , hence carboxylate ion more stablised. This is  also called Ortho effect.

Note:  However for groups like -NH₂ or -OH does not experience SIR effect due to small size and –CN is linear group so SIR effect not applicable.

Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?

2-Methyl Benzoic acid (or o-toluic acid) is stronger than benzene and it's methyl derivatives because steric inhibition of resonance (SIR effect)  due to this effect the carboxyl group being out of the plane of the aromatic ring.The carboxy group being out of the plane in 2-methyl benzoic acid, which inhibiting +R effect and eliminates the factor of +H and increase acidic character of benzoic acid.

Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?

AIcohols and phenols. borh are acidic in nature because they Iiberate H+ with active metals. But alcohols are weaker acids than phenols because,  

Experimentally the pKa value of 4-Methylbenzoic acid (Pka= 4.362), 3 -Methylbenzoic acid (Pka=4.269), Benzoic acid (pKa=4.19), 2-Methylbenzoic (Pka=3.90).

Hence acidic order is :

2-Methyl Benzoic acid > benzoic acid > 3–Methylbenzoic acid > 4-Methylbenzoic acid 

The methyl group at ortho (2nd position) and para (4-position) destabilises Negative charge of corresponding Carboxylate ion by both +I effect (ERG)) as well as by +H (hyperconjugation). But at meta position only +H effect by methyl  does not affect the carboxylate.(From here only +I effect operates). So we can easily understand that m-isomer is more acidic than para-isomer.

2-Methyl Benzoic acid (or o-toluic acid) is stronger than benzene and it's methyl derivatives because steric inhibition of resonance (SIR effect) due to this effect the carboxyl group being out of the plane of the aromatic ring. The carboxy group being out of the plane in 2-methyl benzoic acid, which inhibiting +R effect and eliminates the factor of +H and increase acidic character of benzoic acid.

What is Steric Inhibition of Deprotonation effect ? Or SID effect ?

We know that picric acid is weak acid than expected this is fact that when picric acid releases a proton it becomes an anion for which repulsion results between oxygen atoms of phenoxide ion and oxygen of nitrate group, commonly known as Steric Inhibition of Deprotonation (SID effect). This also results in slight unstability of phenoxide ion and also decrease acidity. Thus picric acid is a weak acid than expected ever.

Related Questions:

1. Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?
2. Benzamide is less easily hydrolysed than methyl benzoate. Why ?
3. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
4. Which is more acidic 2-methyl benzoic acid , 3-methyl benzoic acid or 4-methyl benzoic acid.?
5. Why is o-toluic acid (2-methyl benzoic acid) stronger than benzoic acid ?
6. What is the ortho effect? Why are nearly all ortho substitute benzoic acids (except some groups) stronger acid than benzoic acid?
7. Name of groups which does not show ortho effect in benzoic acid?
8. Why Picric acid (2,4,6-trinitrophenol) is weak acid then expected ?
9. What is Steric Inhibition of Deprotonation effect ? Or SID effect ?
10. Alcohols and Phenols both are acidic but phenols are more acidic. Why?
11. Among orthochlorophenol and orthofluorophenol, which will be a stronger acid and why?
12. Why The phenoxide ion is more stable than phenol ?
13. What is correct acidic strengths order of the haloforms acids ? Give correct explanation.
14. Lower aliphatic acids having 1 to 5 carbons are soluble in water but higher fatty acids having six or more than six carbon are insoluble in water but soluble in alcohol. Explain.
15. Phenoxide ion is more stable than an alkaoxide. why?
16. Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?
17. Chloroform is more acidic than fluoroform why?
18. Fluorine is more electronegative than chlorine even then, p-flurobenzoic acid is weaker acid than p-chlorobenzoic acid explain ?

Alcohols and Phenols both are acidic but phenols are more acidic. Why?

Alcohols and phenols both are acidic in nature because they Liberate H2 with active metals. But alcohols are weaker acids than phenols because,  

(i) Alcohols fail to turn blue litmus red:

(ii) Alcohols fail to neutralize alkalies whereas phenols do so:

(1) Both phenol and phenoxide ions exhibit resonance, whereas alcohols and alkoxide ion do not.
(2) Due to resonance, positive charge 's developed over "O" of phenol this weakens O-H bond and facilitates release of a proton. On the other hand due to electron donating nature of alkyl group -O-H bond is strengthened. Therefore it hinders the release of proton.      

(3) The phenoxide ion is more stable than phenol, due to greater dispersal of negative charge, therefore. Equilibrium get shifted to forward direction. whereas alkoxide ion is less stable than alcohols due to intensification of negative charge, so equilibrium get shifted towards backward direction. Hence phenols are more acidic than alcohols. 

Related Questions:

Benzamide is less easily hydrolysed than methyl benzoate. Why ?

Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?

Phenoxide ion is more stable than an alkaoxide. why?

Benzamide is less easily hydrolysed than methyl benzoate. Why ?

We know that N is less electronegative than oxygen therefore. N can donate a pair of electrons more readily than oxygen.  Therefore, magnitude of positive charge on carbonyl carbon in benzamide is less than in methyl benzoate. Thus during hydrolysis, attack of -OH- ion on carbonyl carbon in benzamide is difficult than in methyl benzoate. Thus benzamide is less easily hydrolysed than methyl benzoate.

Highly branched carboxylic acids are less acidic than unbranched acids. Explain why?

The carboxylate ion of the branched chain acids is shielded from solvent molecules and thus resists for resonance whereas unbranched acids having lesser solvation effect shows resonance stabilized anion to show more acidic character.