PPh3 Br nBuLi pentane/hexane, r.t. PPh3

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Show a complete arrow pushing reaction mechanism for the reaction below.

The image depicts a chemical reaction scheme involving the transformation of a brominated compound into a product using n-butyllithium (nBuLi) as a reagent. 

### Reaction Details

- **Starting Material:**
  - The starting compound is a brominated aromatic compound with a triphenylphosphine cation (PPh₃⁺) and a bromide anion (Br⁻) attached to a carbon chain linked to a benzene ring.

- **Reagent:**
  - **nBuLi (n-butyllithium):** This is a strong base and organolithium reagent used for deprotonation and metalation reactions.

- **Solvent and Conditions:**
  - **Pentane/Hexane:** A mixture of these nonpolar solvents is used.
  - **r.t. (room temperature):** The reaction takes place at ambient temperature.

- **Product:**
  - The product is an alkene formed by eliminating the bromide group from the starting material, resulting in a compound where the carbon chain is now a vinyl group (CH=CH) linked to an aromatic ring with a triphenylphosphine group (PPh₃).

This reaction illustrates a typical application of n-butyllithium in organic synthesis for the dehalogenation and formation of carbon-carbon double bonds.
Transcribed Image Text:The image depicts a chemical reaction scheme involving the transformation of a brominated compound into a product using n-butyllithium (nBuLi) as a reagent. ### Reaction Details - **Starting Material:** - The starting compound is a brominated aromatic compound with a triphenylphosphine cation (PPh₃⁺) and a bromide anion (Br⁻) attached to a carbon chain linked to a benzene ring. - **Reagent:** - **nBuLi (n-butyllithium):** This is a strong base and organolithium reagent used for deprotonation and metalation reactions. - **Solvent and Conditions:** - **Pentane/Hexane:** A mixture of these nonpolar solvents is used. - **r.t. (room temperature):** The reaction takes place at ambient temperature. - **Product:** - The product is an alkene formed by eliminating the bromide group from the starting material, resulting in a compound where the carbon chain is now a vinyl group (CH=CH) linked to an aromatic ring with a triphenylphosphine group (PPh₃). This reaction illustrates a typical application of n-butyllithium in organic synthesis for the dehalogenation and formation of carbon-carbon double bonds.
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