Talk:N-Butyllithium

message: The article text says that this compound "reacts violently with water", but the NPFA 704 thing in the sidebar does not show the W symbol.  Are these both correct?  --Jonadab, 2007 Mar 17
:Its reaction with water is energetic enough to ignite it or its solvent. T-butyllithium bursts into flame in air. --Vuo 18:03, 19 March 2007 (UTC)
thread_title: Reacts with Water?

message: The equation for reaction with butyllithium with R-H to give R-Li, while in principle reversible, is in actual practice, virtually never so. I propose that the reversible arrows be replaced by a right-arrow. ChemistHans 00:11, 19 August 2007 (UTC)
thread_title: Metalation

message: The article implies butyl lithium degrades to lithium hydride (the white precipitate).  Uh well as a chemist I will have to challenge this.  Someone show me the mechanism by which it does this.  Or did they mean Lithium hydroxide?  I can tell you this, when BuLi comes into contact with "water" in the air, it goes to lithium hydroxide.  I can't imagine it going to Lithium hydride over time in the bottle.  —Preceding unsigned comment added by 72.194.216.17 (talk) 08:02, 17 November 2008 (UTC)
replies: text: Beta-hydride elimination to alkene and lithium hydride. --Vuo (talk) 08:21, 18 November 2008 (UTC)
thread_title:  Lithium Hydride? 

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thread_title:  External links modified (February 2018) 

message: Hi folks. I am not by any stretch a chemist (though I have on more than one occasion been promoted temporarily into that capacity being the only one in a room full of engineers and physicists foolish enough to admit to having some memory of my chem 101), but looking at the illustrations of n-BuLi, I see an assembly whose stoichiometric formula, for both the tetra and hexamer, comes out to C4H9Li2, so please could someone explain (in the article itself would be nice, for non-wizards like myself trying to gain some entry to the arcana) how the formula is computed to be C4H9Li?172.103.138.179 (talk) 11:42, 16 August 2018 (UTC)
replies: text: In the illustrations for both the tetramer and the hexamer, the ratio of butyl groups (C4H9) to lithium atoms is 1:1 so the formula comes out to C4H9Li in each case.  -- Ed (Edgar181) 11:53, 16 August 2018 (UTC)
thread_title:  Stoichiometry 

message: In the article it states that n-buLi is electron deificient so it readily reacts with lewis bases. How is this true if n-BuLi is itself a superbase? It should be highly reactive towards Lewis acids, no?  — Preceding unsigned comment added by Crlhermitte (talk • contribs) 01:58, 21 January 2020 (UTC)
replies: text: Lewis acidity is related to electron deficiency.  Basicity is related to the energy of the HOMO.  This thing has got both going on.  It needs electrons (it = "Li+" part) and t-Bu "anion" has high energy valence electrons.  --Smokefoot (talk) 12:59, 21 January 2020 (UTC)
thread_title:  Superbase that is electron deficient?