Comments on: How to Use a pKa Table https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/ Mon, 05 Aug 2024 09:36:01 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-702143 Mon, 05 Aug 2024 09:36:01 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-702143 In reply to xiao liu.

Good catch. Thank you. I re-worded the sentence to make it more clear. Much appreciated!

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By: James Ashenhurst https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-702138 Mon, 05 Aug 2024 09:17:05 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-702138 In reply to xiao liu.

Yes. While it’s true that a weaker base forms a stronger base, it’s still an equilibrium, where the concentration of deprotonated ester is about 1 x 10-9 relative to the concentration of alkoxide. However, that deprotonated ester is then immediately consumed in a reaction (the Claisen condensation, which results in formation of an alkoxide base). As deprotonated ester is consumed, the equilibrium then re-establishes itself (Le Chatelier’s principle). In this way eventually all the ester is converted into the final reaction product.

It goes to show how fast chemical reactions can be when an equilibrium difference of 1 x 10-9 can still result in a reaction going to completion.

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By: xiao liu https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-702096 Mon, 05 Aug 2024 02:32:41 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-702096 Can I ask a question about this sentence? “One example of this rule of thumb in practice is the Claisen Condensation, where alkoxide bases (pKa of alcohols = 15-16) are capable of deprotonating esters (pKa = 25).” It seems that a weaker base forms a stronger base because the esters is a weaker acid compared with alcohols so its conjugated base is stronger.

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By: xiao liu https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-701989 Sat, 03 Aug 2024 14:02:05 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-701989 “Since pretty much everything is less acidic than a deprotonated alkane, this means that they can deprotonate, well, pretty much anything. [Note 7]”. Should we replace the acid with alkalinity in this sentence?

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By: pKa Table of Common acids https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-669214 Wed, 30 Aug 2023 08:31:26 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-669214 […] https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#five […]

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By: James Ashenhurst https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-652291 Thu, 13 Apr 2023 22:44:20 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-652291 In reply to brandon mcevoy.

Where’s the typo? That’s what the reaction is called, but neither the name or mechanism is important for comparing the relative strengths of the bases.

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By: brandon mcevoy https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-652288 Thu, 13 Apr 2023 22:00:23 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-652288 “Here is another examnple of a substitution reaction, known as nucleophilic acyl substitution. Don’t worry about the name or the mechanism for now.” corect ur typo

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By: James Ashenhurst https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-646694 Tue, 24 Jan 2023 19:51:07 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-646694 In reply to Jamie Batten.

Fixed. Grateful to you for spotting the typo!

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By: Jamie Batten https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-646641 Tue, 24 Jan 2023 00:47:52 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-646641 Hi James, marvellous post as usual. I think I’ve spotted a tiny error. At the end of section 3 you state that “Acid base reactions will favor formation of the acid with the lower pKa value”. I think this shoudl read “…the acid with the HIGHER pKa value”, as weaker acids have higher pKa values (and lower Ka values), right? Cheers, Jamie.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/#comment-641215 Thu, 27 Oct 2022 15:50:03 +0000 http://masterorganicchemistry.wordpress.com/?p=906#comment-641215 In reply to Purushotham.

I don’t have a good value for that. If you find one let me know.

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