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Lithium aluminium hydride (LAH) is widely used in organic chemistry as a reducing agent. [5] It is more powerful than the related reagent sodium borohydride owing to the weaker Al-H bond compared to the B-H bond. [23]
Reductions of α,β-unsaturated carbonyl compounds may occur in a 1,2 sense (direct addition) or a 1,4 sense (conjugate addition). The tendency to add in a 1,4 sense is correlated with the softness of the hydride reagent according to Pearson's hard-soft acid-base theory. [7]
Stoichiometric reducing agents to accomplish this task include lithium aluminium hydride, sodium borohydride, alkoxy borohydrides, alkoxy aluminium hydrides, and boranes. Although stoichiometric chiral reducing agents often afford products with high enantioselectivity, the necessity of a stoichiometric amount of chiral material is a disadvantage.
The central metal (usually B vs Al) strongly influences reducing agent's strength. Aluminum hydrides are more nucleophilic and better reducing agents relative to borohydrides. [5] The relatively weak reducer sodium borohydride is typically used for reducing ketones and aldehydes. It tolerates many functional groups (nitro group, nitrile, ester ...
The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry.
Hydrogen gas is a reducing agent when it reacts with non-metals and an oxidizing agent when it reacts with metals. 2 Li (s) + H 2(g) → 2 LiH (s) [ a ] Hydrogen (whose reduction potential is 0.0) acts as an oxidizing agent because it accepts an electron donation from the reducing agent lithium (whose reduction potential is -3.04), which causes ...
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Some amides can be reduced to aldehydes in the Sonn-Müller method, but most routes to aldehydes involve a well-chosen organometallic reductant.. Lithium aluminum hydride reduces an excess of N,N-disubstituted amides to an aldehyde: [citation needed]