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### 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 ...
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### 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 ...
28 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 ...
656 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 ...
19k 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, ...
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### Basicity Alteration Due To Ortho Effect In Methoxy Aniline System

I wanted to ask something more in reference to this question Ortho-effect in substituted aromatic acids and bases Suppose instead of toluidine, 2-methoxyaniline and 3-methoxyaniline are present. Now ...
20k 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 ...
6k 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: ...
15k 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 ...
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### 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 ...
2k 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 ...
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### Why is p-toluidine more basic than m-toluidine?

https://en.wikipedia.org/wiki/Toluidine In m-toluidine the $\ce{CH3}$ group is closer to $\ce{N}$ so shouldn't that increase the electron density on $\ce{N}$ and make it a stronger base?