Linked Questions

9 votes
2 answers
23k views

Why is o-toluic acid (2-methylbenzoic acid) more acidic than benzoic acid? [duplicate]

Why does the methyl group at the ortho-position stabilize the carboxylate ion? I recognize that there will be a steric clash between the carboxyl group and the methyl group but I don't understand why ...
RobChem's user avatar
  • 9,784
1 vote
1 answer
2k views

Effect of steric effect on acidic and basic strength [duplicate]

I found a sentence given in my textbook: More is steric effect more is acidic strength of carboxylic acids and more is steric effect less is basic strength of aniline and other amines. Could someone ...
Charlie's user avatar
  • 294
0 votes
0 answers
189 views

H-bonding in o-hydroxybenzoic acid [duplicate]

Amongst all hydroxybenzoic acids the ortho isomer is most acidic and the major reason is intramolecular H-bonding in the anion. My question is that isn't the loss of proton destabilising the molecule ...
FullBridge's user avatar
1 vote
0 answers
78 views

Comparing basicity using inductive effect [duplicate]

In the following two compounds . 1) 2) We have to compare basicity . According to me CH$_3$ is an electron donating compound so in second compound it will increase charge density in nitrogen so ...
Icandoahandstand99's user avatar
1 vote
0 answers
54 views

Methyl group and acidic nature [duplicate]

After reading various answers here on StackExchange (like Why is the methyl group electron-donating via the inductive effect? and Strongest negative inductive effect group between trimethylammonium, ...
gauri agrawal's user avatar
1 vote
0 answers
30 views

Ortho effect and the relative acidity in aromatic acids [duplicate]

What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid? I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
Krish Chaudhari's user avatar
22 votes
4 answers
39k views

Acidity order of nitrophenols

As in other posts I have seen and learnt that, if one is given four compounds, namely para-nitrophenol, ortho-nitrophenol, meta-nitrophenol and phenol and is told to arrange them in order of acidity, ...
Aneek's user avatar
  • 830
15 votes
3 answers
1k views

Why can the lone pair not align with the phenyl moiety in 2,6-xylidine?

I am told that for 2,6-xylidine (2,6-dimethylaniline), the amino group cannot line up in such a way that its p-orbital is parallel with respect to the p-orbitals of the carbons in the ring. I've ...
Dissenter's user avatar
  • 18.8k
16 votes
1 answer
18k views

Basicity Alteration Due To Ortho Effect In Methoxy Aniline System

I wanted to ask something more in reference to this question. Suppose instead of toluidine, 2-methoxyaniline and 3-methoxyaniline are present. Now, why is 2-methoxyaniline more basic than 3-...
user avatar
15 votes
2 answers
17k views

Is steric inhibition of resonance or steric inhibition of protonation dominant in o-toluidine?

I wish to know which effect out of steric inhibition of resonance (SIR) or steric inhibition of protonation (SIP) is dominant over the other when comparing basicities of o-toluidine and aniline: ...
Shrish Shankar's user avatar
12 votes
2 answers
2k views

Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?

If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows: Even after deprotonation, it has intramolecular hydrogen bonding as follows: My question: p-...
Neha's user avatar
  • 452
16 votes
1 answer
36k views

Why is benzoic acid a stronger acid than acetic acid?

Why is benzoic acid ($\mathrm{p}K_\mathrm{a} = 4.20$) a stronger acid than acetic acid ($\mathrm{p}K_\mathrm{a} = 4.76$), even though the conjugate base in case of benzoic acid is destabilized due to ...
Abhirikshma's user avatar
  • 1,906
8 votes
2 answers
10k views

Why is ortho-hydroxybenzoic acid more acidic than its para-isomer?

Why is ortho-hydroxybenzoic acid $(\mathrm{p}K_\mathrm{a} = 2.98)$ more acidic than its para-isomer $(\mathrm{p}K_\mathrm{a} = 4.58)$? March's Advanced Organic Chemistry (7th ed) gives the reason to ...
Archer's user avatar
  • 5,463
6 votes
1 answer
24k views

Acidic Strength of Nitrobenzoic Acid

The Correct acidic strength of the following : But according to me pK value of 2-nitro benzoic acid should be more than 4-nitro benzoic acid because NO2 might have H-bonding with COOH as NO2 have it ...
TheNewGenGamer's user avatar
2 votes
2 answers
3k views

How to rationalise the basicity order of phenylenediamine?

Why is the basicity of para- > meta- > aniline > ortho- for phenylenediamine? ($\mathrm pK_\mathrm a$: ortho: 9.53, meta: 9.12, para: 7.96) I tried deducing it using resonance and inductive effects ...
user avatar

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