Comments on: The Three Classes of Nucleophiles https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/ Fri, 17 Jan 2025 11:23:45 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-720344 Wed, 18 Dec 2024 16:45:44 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-720344 In reply to Aditya Srivastava.

The problem with NH2(-) as a nucleophile is that it is extremely basic and often performs side reactions.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-720343 Wed, 18 Dec 2024 16:45:02 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-720343 In reply to Charlie.

It is more difficult for triple bonds to undergo reaction with strong acids such as H-Cl since it would result in a vinyl cation, which, being sp-hybridized, is a less stable carbocation than alkyl carbocations. Essentially you want to avoid having empty orbitals with a lot of s-character.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-720341 Wed, 18 Dec 2024 16:43:40 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-720341 In reply to ALY Hassan.

Ethene can be a nucleophile, yes. It can react with dihalogens such as Cl2, Br2, and I2 for example.

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By: ALY Hassan https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-621010 Thu, 17 Feb 2022 23:42:49 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-621010 Is ch2ch2 neucleophiles?

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By: Charlie https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-608343 Mon, 25 Oct 2021 10:50:00 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-608343 Why triple bond is weak nucleophile than double bond?

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By: Aditya Srivastava https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-593770 Fri, 08 Jan 2021 18:07:58 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-593770 Can you explain why OH- is a stronger nucleophile than NH2- in a polar aprotic solvent like DMF?

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By: BJ https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-582062 Thu, 09 Jul 2020 07:25:10 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-582062 Ok, after further research let me see if I have my thought processes in order.
1.) when moving across a row nucleophilicity follows basicity. The less electronegative an atom is the more basic it is.

2.)When going down a group it is not so simple. Nucleophilicity does not necessarily mirror basicity. This idea stems from the fact that when we consider an negatively charged ion as a nucleophile we must take into consideration the type of solvent used.If a polar protic solvent is used, the nucleophile will be hindered from being able to share its electrons in attacking an electrophile because the protic solvent will hydrogen bond and form a solvation shell around the nucleophile. Basically, this means that larger anions, which are more polarizable, will be more nucleophilic because their electrons will be less hindered when compared to smaller anions in their group.Thus, in this case nucleophilicity increases as you go down a group, not up a group.

3.)However, if you use a polar apriotic solvent on a negatively charged ion no hydrogen bonding occurs.Thus, no solvation shell. In consequence, you will have nucleophilicty following basicity up or down the column(Note: I have read that even then this is not always the case.Could you elaborate?)

4.)When it concerns nucleophiles that are uncharged size dicatates nucleophilicity.The larger the atom the greater a nucleophile it is.
5.) Sterically hindered nucleophiles react more slowly.

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By: BJ https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-582034 Wed, 08 Jul 2020 13:23:05 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-582034 The third trend of nucleophilicity of lone pairs states-nucleophilicity increases as you go down the periodic table .Do we always assume nucleophilicity always increases as we go down any group in the periodic table or must we always consider the solvent along with this trend?Please explain.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-579667 Mon, 27 Apr 2020 16:29:25 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-579667 In reply to Dezső.

Nucleophilicity is solvent-dependent. Polar protic solvents can hydrogen bond with halides. F- is most basic, but also forms strongest hydrogen bonds, and will carry around with it a shell of solvent molecules which hinder nucleophilicity. That is why F- is the worst nucleophile among halides in polar protic solvents.

In polar aprotic solvents trend is reversed; F- is best nucleophile, I- worst. See this post on solvents:
https://www.masterorganicchemistry.com/2012/04/27/polar-protic-polar-aprotic-nonpolar-all-about-solvents/

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By: Dezső https://www.masterorganicchemistry.com/2011/03/04/the-three-classes-of-nucleophiles/#comment-579632 Sun, 26 Apr 2020 16:04:18 +0000 https://www.masterorganicchemistry.com/?p=1380#comment-579632 (I know this post is really old but trying does no harm)
In a previous post you mentioned that electronegativity increases the stability of negative charge (therefore basicity as well)
But as you said in this post, F(-) is the worst nucleophile despite havint the most basicity (if I’m not mistaken)
So does it mean that nucleophility DEcreases with basicity? (Sorry if I’m asking nonsense, I’m just a high school student interested in org chem ><)

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