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1 vote
1 answer
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Determining the order of basicity of acetate, phenoxide, hydroperoxide, and hydroxide ions [duplicate]

Arrange the following ions in order of basicity: (1) $\ce{CH3COO-}$ (acetate) (2) $\ce{PhO-}$ (phenoxide) (3) $\ce{HOO-}$ (hydroperoxide) (4) $\ce{HO-}$ (hydroxide) The first thing I see is ...
Shubham's user avatar
  • 501
1 vote
1 answer
496 views

Acidity of phenol and carboxylic acid [duplicate]

Carboxylic acid is much more acidic than phenol ($\mathrm{pK}_\mathrm{a}$ difference of ~6). I wonder why? In terms of resonance, there are 5 resonance structures for phenol, and only 2 in carboxyl ...
user96067's user avatar
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0 votes
0 answers
139 views

Why methanoic acid is more acidic than phenol? [duplicate]

If you draw the resonatic structure, obviously, the conjugate base of phenol seems to be more stabilized than methanoic acid's. Then why this anomaly?
MrObjectOriented's user avatar
18 votes
3 answers
14k views

Why does having equivalent resonance structures give more stability?

Although the phenolate ion has more resonance structures (4) compared to acetate ion (2), acetate is more stable because it has two equivalent resonance structures of same energy. Why does having ...
Heisenberg's user avatar
4 votes
2 answers
3k views

Are aromatic amines or amides less basic?

When the lone pair of an amino group $\ce{R-NH2}$ is involved in resonance, its basicity decreases. But, between conjugation with carbonyl group $\ce{R}=\ce{R'CO}$ or resonance with benzene $\ce{R} = \...
Rajath Radhakrishnan's user avatar
4 votes
1 answer
1k views

Comparing the basicities of guanidine, acetamidine, benzamine, and dimethylamine

The following compounds were given, and I have to predict their order of basicity: Compound Name Chemical formula A Guanidine $\ce{(H2N)2C(NH)}$ B Acetamidine $\ce{(H3C)(H2N)C(NH)}$ C Benzamidine $...
Prakhar's user avatar
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0 votes
1 answer
2k views

Acidic nature comparison; benzoic acid and phenylacetic acid

The $\ce{pK_a}$ values of benzoic acid and phenylacetic acid are around 4.2 and 4.31 respectively. In benzoic acid, you have the resonance being the dominating effect, destabilizing a conjugate base ...
harry's user avatar
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5 votes
1 answer
610 views

Why is ethanoic acid more acidic than phthalimide?

Why is ethanoic acid more acidic than phthalimide? $\mathrm{p}K_\mathrm{a}$ of phthalimide is 8.3 (source), while that of ethanoic acid is 4.76 (source). Applying the logic found here would suggest ...
DefinitelyNotAPlesiosaur's user avatar
1 vote
0 answers
424 views

Acidity comparison between 4-hydroxybenzaldehyde and methanoic acid

Acidity is dependent on charge dispersal. Greater the charge dispersal in conjugate base greater the acidity (assuming that both acids being compared have similar stablities). So in the case of 4-...
Ramesh Agarwal's user avatar
0 votes
0 answers
72 views

Quantity vs quality in determining acidic strength

Consider the following order of acidity based on pKa values:- ethanoic acid > phthalimide >phenol >water >acetamide Looking towards similar questions on stack exchange such as this , the ...
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