Comments on: What Makes A Good Nucleophile?

By: What Makes A Good Nucleophile? | Straight A Mindset

What Makes A Good Nucleophile? | Straight A Mindset — Thu, 07 Dec 2023 22:33:09 +0000

[…] Electronegativity: Across The Periodic Table, Nucleophilicity Increases With Decreasing Electronegat… […]

By: Rohan Khan

Rohan Khan — Tue, 22 Sep 2020 09:23:36 +0000

Dear Sir.
You are the best.
I love the way in which you explain these terms in correct order and sequence….starting from the very basic terms.
You have cleared, all my confusion.
Everyone can easily understand,as you have explained in very proper manner.

By: James Ashenhurst

James Ashenhurst — Thu, 21 Nov 2019 21:41:09 +0000

In reply to Raj. Cyanide ion is more nucleophilic, and the lone pair that is transferred is the carbon. Otherwise the result would have a positively charged nitrogen and a negatively charged carbon.

By: Raj

Raj — Thu, 21 Nov 2019 19:07:29 +0000

This was life saving for me!
But, tell me which one has more nucleophilicity CN(-) or OH(-)…and which electron pair is actually transferred in CN(-)..that of carbon or nitrogen?

By: James Ashenhurst

James Ashenhurst — Wed, 18 Sep 2019 20:55:46 +0000

In reply to karthika. I think you mean hydride source? The isopropyl C-H bond is weaker.

By: James Ashenhurst

James Ashenhurst — Wed, 18 Sep 2019 16:15:23 +0000

In reply to Hosni Elwan. Hydroxide ion - it is a stronger base.

By: James Ashenhurst

James Ashenhurst — Fri, 13 Sep 2019 17:08:53 +0000

In reply to AAKASH. Which will be a stronger base? Can you find a pKa table to give you the values for H2O and CH3OH? That will tell you which will be a stronger base, since the weaker the acid, the stronger the conjugate base.

By: James Ashenhurst

James Ashenhurst — Fri, 13 Sep 2019 16:25:56 +0000

In reply to piku singh. 1. Charged species generally more nucleophilic than neutral species ("the conjugate base is always a stronger nucleophile"). 2. The more basic a species is, generally, the more nucleophilic it is. Lots of exceptions, but not within the series you mention here.

By: James Ashenhurst

James Ashenhurst — Thu, 05 Sep 2019 18:09:30 +0000

In reply to arun. If one follows the same logic that the higher one goes on the periodic table, the more it will hydrogen-bond, then (CH3)3P will be more nucleophilic than (CH3)3N in polar protic solvents, and (CH3)3N will be more nucleophilic in polar aprotic solvents.

By: James Ashenhurst

James Ashenhurst — Thu, 05 Sep 2019 18:04:01 +0000

In reply to Varun. In polar protic solvents, the order of nucleophilicity will be I- > Br- > Cl- > F- . This reflects the extent of hydrogen bonding around each ion (I- least, F- most). In polar aprotic solvents, the order reverses: F- > Cl > Br- > I- , since hydrogen bonding is not a factor, and F- tends to be more basic, as well as forms stronger bonds.