Comments on: Acid Base Reactions Are Fast https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/ Sun, 22 Jun 2025 18:45:54 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-754979 Sun, 22 Jun 2025 18:45:54 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-754979 In reply to Hopy J.

That’s principle of least action. This is principle of least nuclear motion. Different thing.

https://www.sciencedirect.com/science/article/abs/pii/S0065316008601173?via%3Dihub

In many acid-base reactions, the structure of the transition state greatly resembles that of the reactants; very little atomic reorganization is required.

In nucleophilic substitution (and other) reactions, there is re-organization of the atoms in the transition state versus the starting materials. That re-organization requires more energy.

That said, I should probably re-write this to clarify.

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By: Hopy J https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-754951 Sun, 22 Jun 2025 12:43:19 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-754951 The essence of Richard Feynman’s path integral formulation is that every possible trajectory contributes to the particle’s behaviour with a certain probability amplitude. Only when the contributions of paths interfere with each other in the classical limit lead to principle of least action? How can the principle of least action be applied to atomic motion if they are at the quantum scale?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-582092 Thu, 09 Jul 2020 17:25:02 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-582092 In reply to Deepansh Kalra.

Grignard reagents add to the carbonyl – irreversibly. Hydroxide can add to the carbonyl to form a hemiacetal but it is reversible, and eventually deprotonation occurs to give the enolate.
With Grignards, deprotonation at the alpha position only tends to occur when there is a lot of steric bulk around the carbonyl carbon. The C-H bond has to be oriented at 90° in order for deprotonation to occur, otherwise the resulting carbanion won’t be in resonance with the carbonyl pi bond

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By: Deepansh Kalra https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-581939 Sun, 05 Jul 2020 13:43:59 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-581939 Why in Aldol Condensation OH- being a weaker base than Grignard Reagent able to deprotonate alpha H and Grignard Reagent Isn’t

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By: Jade https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-511374 Mon, 17 Apr 2017 21:56:40 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-511374 In reply to James.

Thank you James for your reply!

I purchased the summary, and realized I wasn’t ready for summary yet, and going through the posts now, and it’s really helpful. I just thought it will be really good if you can put together these post contents into printable pdf. I would definitely pay a reasonable price to have this contents easier to read, carry, and make notes..!

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By: James https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-511371 Mon, 17 Apr 2017 21:37:34 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-511371 In reply to Alyssa Sak.

Any time you form a carbocation, watch out for rearrangements.

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By: James https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-511370 Mon, 17 Apr 2017 21:36:59 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-511370 In reply to Jade.

Hi, if you deprotonate C-H adjacent to a ketone, the carbon will not be sp3 hybridized for long. It is energetically favourable for the carbon to re-hybridize to sp2, which puts the lone pair in a p orbital and can then be conjugated with the p orbitals in the C=O group.

It’s this atomic motion which makes deprotonation of C-H “slow”.

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By: Jade https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-511330 Mon, 17 Apr 2017 05:55:15 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-511330 Thank you so much for all your work on the website. I got orgo 1 summary sheet and finding it very helpful.
Just a question. Why breakage of C-H bond results in rehybridazation om aldehyde and ketone?
Wouldn’t it be still sp3 with the lone pair after deprotonation?
There is no
Thank you again.

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By: Diana https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-449183 Thu, 03 Mar 2016 22:46:06 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-449183 Thanks so much for summarizing!
I’ve always had trouble understanding why certain actions are preferred over others. It’s an important point that you clarified so well!
Thank you!

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By: Alyssa Sak https://www.masterorganicchemistry.com/2012/05/21/acid-base-reactions-are-fast/#comment-93852 Fri, 09 May 2014 12:41:31 +0000 https://www.masterorganicchemistry.com/?p=5073#comment-93852 Forgot to add that yes, I realize the shifts can be used in SN1 / SN2 reactions…maybe it’s best if I keep an eye out for any potential carbocation rearrangements that could make a carbon center more stable.

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