Linked Questions

7
votes
2answers
14k 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 ...
2
votes
0answers
66 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 ...
0
votes
0answers
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 ...
10
votes
3answers
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 ...
15
votes
4answers
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, ...
12
votes
1answer
12k views

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 ...
8
votes
2answers
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 ...
7
votes
2answers
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: ...
2
votes
1answer
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 ...
6
votes
2answers
3k 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 ...
2
votes
2answers
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 ...
2
votes
1answer
3k views

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?
3
votes
1answer
2k views

Comparing the basicity of aniline and ortho anisidine

In my worksheet there is a question that asks for the comparison of basicities of the three anisidine isomers and aniline: After my analysis using: $\text{Basicity} \propto \text{+M effect (except ...
4
votes
0answers
1k views

Why is o-fluorophenol a stronger acid than p-fluorophenol?

The $\mathrm{p}K_\mathrm{a}$ value of o-fluorophenol is $8.7$, while that of the p-fluorophenol is $9.9$. It's obvious that the inductive effect is more dominant at ortho-position, which results in a ...
6
votes
1answer
834 views

Steric inhibition of resonance vs. hydrogen bonding

I have to compare the acidic strength of these compounds: Now, in A and B hydrogen bonding will be present which will help stabilize the negative charge of the conjugate base. However, the hydroxyl ...

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