Related Experiment Video
Updated: Jun 1, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Unnatural isotopic composition of lithium reagents
1U.S. Geological Survey, 431 National Center, Reston, Virginia 20192.
Abstract:
Isotopic analysis of 39 lithium reagents from several manufacturers indicates that seven were artificially depleted in (6)Li significantly in excess of the variation found in terrestrial materials. The atomic weight of lithium in analyzed reagents ranged from 6.939 to 6.996, and δ(7)Li, reported relative to L-SVEC lithium carbonate, ranged from -11 to +3013‰. This investigation indicates that (6)Li-depleted reagents are now found on chemists' shelves, and the labels of these (6)Li-depleted reagents do not accurately reflect the atomic and (or) molecular weights of these reagents. In 1993, IUPAC issued the following statement: "Commercially available Li materials have atomic weights that range between 6.94 and 6.99; if a more accurate value is required, it must be determined for the specific material." This statement has been found to be incorrect. In two of the 39 samples analyzed, the atomic weight of Li was in excess of 6.99.
Related Concept Videos
Weak Acid Solutions
Acid Halides to Alcohols: LiAlH4 Reduction
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
Inductively Coupled Plasma-Mass Spectrometry (ICP-MS): Interferences
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Qualitative Analysis
For instance, group IV...
Ionic Bonding and Electron Transfer

