Why is Acetic acid (pKa = 4.76) stronger than carbonic acid (pKa = 6.36)?Why is carbonic acid a weaker acid...
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Why is Acetic acid (pKa = 4.76) stronger than carbonic acid (pKa = 6.36)?
Why is carbonic acid a weaker acid than acetic acid?Is oxygen with a positive charge more stable? (comparison of canonical structures)Why is formic acid a stronger acid than acetic acid?Why is o-toluic acid (2-methylbenzoic acid) more acidic than benzoic acid?Why is benzyl alcohol a slightly stronger acid than cyclohexanol?Find the order of acidic strengthExtent of dehydration by conc sulphuric acidWhy is benzoic acid a stronger acid than acetic acid?I am confused about the stability of carbanion III and IV in the imageWhy is carbonic acid a weaker acid than acetic acid?Which of these carbocations are more stable?
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In order to try and understand this, I evaluated it via stability of conjugate bases. The acetate vs carbonate ion. The only difference is what's attached to the carboxyl group, the -CH3 and the -OH. Both anions seem to have equal resonance structures as I think resonance mainly only happens on the carboxyl group.
I think that because the methyl group is just larger than the hydroxyl group, it is able to better stabilize the negative charge on the molecule overall. But I also remember hearing that carbon can have a positive inductive effect, meaning it pushes electron density toward the carboxyl group, which would make it less stable.
I originally thought that carbonate would be more stable because the oxygen would pull the electron density toward itself, making the charge more evenly distributed.
If somebody could explain with diagrams I would appreciate it. I lost access to my software that did electron modeling functions for me :(.
organic-chemistry stability
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
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$endgroup$
add a comment |
$begingroup$
In order to try and understand this, I evaluated it via stability of conjugate bases. The acetate vs carbonate ion. The only difference is what's attached to the carboxyl group, the -CH3 and the -OH. Both anions seem to have equal resonance structures as I think resonance mainly only happens on the carboxyl group.
I think that because the methyl group is just larger than the hydroxyl group, it is able to better stabilize the negative charge on the molecule overall. But I also remember hearing that carbon can have a positive inductive effect, meaning it pushes electron density toward the carboxyl group, which would make it less stable.
I originally thought that carbonate would be more stable because the oxygen would pull the electron density toward itself, making the charge more evenly distributed.
If somebody could explain with diagrams I would appreciate it. I lost access to my software that did electron modeling functions for me :(.
organic-chemistry stability
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
2
$begingroup$
Possible duplicate of Why is carbonic acid a weaker acid than acetic acid?
$endgroup$
– Mithoron
1 hour ago
add a comment |
$begingroup$
In order to try and understand this, I evaluated it via stability of conjugate bases. The acetate vs carbonate ion. The only difference is what's attached to the carboxyl group, the -CH3 and the -OH. Both anions seem to have equal resonance structures as I think resonance mainly only happens on the carboxyl group.
I think that because the methyl group is just larger than the hydroxyl group, it is able to better stabilize the negative charge on the molecule overall. But I also remember hearing that carbon can have a positive inductive effect, meaning it pushes electron density toward the carboxyl group, which would make it less stable.
I originally thought that carbonate would be more stable because the oxygen would pull the electron density toward itself, making the charge more evenly distributed.
If somebody could explain with diagrams I would appreciate it. I lost access to my software that did electron modeling functions for me :(.
organic-chemistry stability
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
In order to try and understand this, I evaluated it via stability of conjugate bases. The acetate vs carbonate ion. The only difference is what's attached to the carboxyl group, the -CH3 and the -OH. Both anions seem to have equal resonance structures as I think resonance mainly only happens on the carboxyl group.
I think that because the methyl group is just larger than the hydroxyl group, it is able to better stabilize the negative charge on the molecule overall. But I also remember hearing that carbon can have a positive inductive effect, meaning it pushes electron density toward the carboxyl group, which would make it less stable.
I originally thought that carbonate would be more stable because the oxygen would pull the electron density toward itself, making the charge more evenly distributed.
If somebody could explain with diagrams I would appreciate it. I lost access to my software that did electron modeling functions for me :(.
organic-chemistry stability
organic-chemistry stability
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
asked 2 hours ago
Abdullah AfridiAbdullah Afridi
111
111
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
New contributor
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
Abdullah Afridi is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
2
$begingroup$
Possible duplicate of Why is carbonic acid a weaker acid than acetic acid?
$endgroup$
– Mithoron
1 hour ago
add a comment |
2
$begingroup$
Possible duplicate of Why is carbonic acid a weaker acid than acetic acid?
$endgroup$
– Mithoron
1 hour ago
2
2
$begingroup$
Possible duplicate of Why is carbonic acid a weaker acid than acetic acid?
$endgroup$
– Mithoron
1 hour ago
$begingroup$
Possible duplicate of Why is carbonic acid a weaker acid than acetic acid?
$endgroup$
– Mithoron
1 hour ago
add a comment |
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Well actually the $mathrm{pK}_mathrm{a1}$ for carbonic acid at 25 °C is 3.6. The pka = 6.36 is also including the equilibrium with dissolved $ce{CO2}$ in aqueous solution.
answered 2 hours ago
MaxWMaxW
14.8k12158
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1 Answer
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$begingroup$
Well actually the $mathrm{pK}_mathrm{a1}$ for carbonic acid at 25 °C is 3.6. The pka = 6.36 is also including the equilibrium with dissolved $ce{CO2}$ in aqueous solution.
answered 2 hours ago
MaxWMaxW
14.8k12158
$endgroup$
add a comment |
$begingroup$
Well actually the $mathrm{pK}_mathrm{a1}$ for carbonic acid at 25 °C is 3.6. The pka = 6.36 is also including the equilibrium with dissolved $ce{CO2}$ in aqueous solution.
answered 2 hours ago
MaxWMaxW
14.8k12158
$endgroup$
add a comment |
$begingroup$
Well actually the $mathrm{pK}_mathrm{a1}$ for carbonic acid at 25 °C is 3.6. The pka = 6.36 is also including the equilibrium with dissolved $ce{CO2}$ in aqueous solution.
answered 2 hours ago
MaxWMaxW
14.8k12158
$endgroup$
Well actually the $mathrm{pK}_mathrm{a1}$ for carbonic acid at 25 °C is 3.6. The pka = 6.36 is also including the equilibrium with dissolved $ce{CO2}$ in aqueous solution.
answered 2 hours ago
MaxWMaxW
14.8k12158
answered 2 hours ago
MaxWMaxW
14.8k12158
answered 2 hours ago
MaxWMaxW
14.8k12158
answered 2 hours ago
MaxWMaxW
14.8k12158
14.8k12158
add a comment |
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$begingroup$
Possible duplicate of Why is carbonic acid a weaker acid than acetic acid?
$endgroup$
– Mithoron
1 hour ago