JoVE Science Education
Organic Chemistry II
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Source: Vy M. Dong and Diane Le, Department of Chemistry, University of California, Irvine, CA
This experiment will demonstrate a simple technique to titrate and obtain an accurate concentration of the organolithium reagent, n-butyllithium (n-BuLi). Organolithium reagents are extremely air- and moisture-sensitive and proper care must be taken to maintain the quality of the reagent so that it may be used successfully in a reaction. The n-BuLi titration experiments should be performed regularly to obtain accurate concentrations prior to use in a chemical reaction. Subsequently, we will demonstrate the addition of the titrated n-BuLi to benzaldehyde.
1. Preparation of Titrant
2. Titration of n-BuLi
Representative results for the titration of n-BuLi for Procedures 1-3
Procedure Step | Color of reaction mixture |
1.1 | Colorless |
2.1 | Yellow, then colorless |
2.2 | Deep yellow |
3.1 | 1.18 mmol diphenylacetic acid/1 mL n-BuLi |
In this experiment, we have demonstrated how to determine the concentration of an n-BuLi solution by using diphenylacetic acid. We have also performed a reaction by adding n-BuLi to benzaldehyde.
Accurate concentrations of n-BuLi are important for its successful application in a number of reactions. n-BuLi is commonly used in lithium-halogen exchange reactions to prepare aryllithium or vinyllithium reagents, which can be subsequently used in C-C bond forming
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