JoVE Science Education

Organic Chemistry II

Aby wyświetlić tę treść, wymagana jest subskrypcja JoVE.

English

n-Butyllithium Titration

Przegląd

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.

Procedura

1. Preparation of Titrant

  1. To a flame-dried round bottom flask equipped with a stir bar under N2, add diphenylacetic acid (250 mg, 1.18 mmol) and anhydrous THF (5 mL).

2. Titration of n-BuLi

  1. Calculate the approximate amount of n-BuLi solution (in hexanes) needed to consume the diphenylacetic acid. Using a syringe, slowly adda solution of n-BuLi dropwise. The reaction mixture will turn temporarily yellow and back to a colorless

Log in or to access full content. Learn more about your institution’s access to JoVE content here

Wyniki

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

Log in or to access full content. Learn more about your institution’s access to JoVE content here

Wniosek i Podsumowanie

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

Log in or to access full content. Learn more about your institution’s access to JoVE content here

Używamy plików cookie, aby ulepszyć Twoje wrażenia z korzystania z naszej witryny.

Kontynuując korzystanie z naszej witryny lub klikając „Kontynuuj”, wyrażasz zgodę na akceptację naszych plików cookie.