Comments on: The Conjugate Acid Is A Better Leaving Group https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/ Fri, 14 Jun 2024 10:02:43 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: KD https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-696681 Fri, 14 Jun 2024 10:02:43 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-696681 On the third line, i feel you messed up with tosylates and mesylates,guess the mesylates will be (MsO-) not (TsO-).
I don’t know it either.Thanks

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-690359 Thu, 11 Apr 2024 16:27:43 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-690359 In reply to Soham Saha.

What really happens in a reaction like this is that there is a large excess of acid, and any H2O that is formed is quickly protonated to give H3O+. H3O+ is not a good nucleophile, so the reaction stops there.

CH3CH2Br *will* react with H2O to give CH3CH2OH, but it is fairly slow and tends to require heat.

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By: Soham Saha https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-690350 Thu, 11 Apr 2024 15:24:20 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-690350 Thanks for this awesome content! I have finally found the ultimate place for learning O-Chem.
I have a little doubt though:
H2O is a much stronger base than Br-, which makes it a worse leaving group than Br-. Then how come this reaction (part of our school syllabus) is possible:
C2H5OH+HBr ——> C2H5Br+H2O ?
Shouldn’t this reaction refuse to go forward (but it’s refusal will be less strong than if the case was C2H5OH+NaBr) ?

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By: Maria https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-646979 Sun, 29 Jan 2023 20:31:02 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-646979 *Is this the correct order : OTS>I>Br>Cl>F?

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By: Maria https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-646978 Sun, 29 Jan 2023 20:27:00 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-646978 If there is MsO- or TsO- and Br- as leaving groups , which of them is weaker base and better leaving groub ?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-557316 Tue, 02 Jul 2019 02:00:49 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-557316 In reply to Karol.

You’ve seen this before, if you think about it. Take water, H2O. Water can act as a base (donating its lone pair of electrons) and also it can act as an acid (donating H+ to give HO-, if you think of it as a Bronsted acid, or accepting a pair of electrons on the H if you think of it as a Lewis acid )

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By: Karol https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-538598 Tue, 25 Sep 2018 09:21:44 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-538598 Hi, i don’t see the bigger picture here.. How can be a conjugate acid a weaker base? How can be acid a base?

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By: Hinesh https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-435300 Fri, 13 Nov 2015 12:09:00 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-435300 In the reaction where the silver cation is used to make Cl a better leaving group, you have an electron pair moving from the chlorine to the silver ion in the mechanism. In the next step, you then have what looks like a covalent bond between silver and chlorine in silver chloride next to the carbcation. I just wanted to check that this is indeed an ionic compound formed (silver chloride) as I thought.

I also want to ask if the first step of the mechanism for that reaction is Lewis acid-base because a covalent bond is initially formed between the chlorine atom and the silver ion. I’m asking this because I think that ordinarily when silver and chloride ions bond ionically to form silver chloride it is not considered lewis acid-base because an electron pair hasn’t been transferred to form a covalent bond. In this case, however, am I right in thinking that the chlorine is part of a bigger molecule and so the bond it forms is covalent and hence that step can be considered Lewis acid-base?

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By: James https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-359972 Mon, 02 Feb 2015 22:47:25 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-359972 In reply to A.

Protonation will be quick, relative to loss of leaving group. The rate limiting step is still first order.

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By: A https://www.masterorganicchemistry.com/2012/08/07/the-conjugate-acid-is-a-better-leaving-group/#comment-359398 Sun, 01 Feb 2015 13:17:03 +0000 https://www.masterorganicchemistry.com/?p=5444#comment-359398 in the example you gave which is sn1, hcl will be in the rate law. So is it the case that sn1 can be 2nd order?

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