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Draw the reaction mechanism for the Wittig reaction of benzyltriphenylphosphonium chloride and...

Question:

Draw the reaction mechanism for the Wittig reaction of benzyltriphenylphosphonium chloride and cinnamaldehyde. Pay special attention to the phospho-oxetene intermediate.

Predict which isomer, cis or trans, will be produced in the greater amount.

Witting Reaction:

Wittig reaction is one of the crucial organic synthesis reactions. It yields an olefinic bond, starting from a phosphonium halide and a carbonyl compound. It carefully switches the {eq}{\rm{C}} = {\rm{O}} {/eq} , {eq}{\rm{C}} = {\rm{P}} {/eq} bond to {eq}{\rm{C}} = {\rm{C}} {/eq} and {eq}{\rm{O}} = {\rm{P}} {/eq} bonds.

Answer and Explanation:


The substrate for the given reaction is benzyltriphenylphosphonium chloride. The molecular formula for benzyltriphenylphosphonium chloride is...

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Learn more about this topic:

The Wittig Reaction & Alkene Synthesis: Definition & Examples
The Wittig Reaction & Alkene Synthesis: Definition & Examples

from Chemistry 304: Organic Chemistry II

Chapter 2 / Lesson 14
543

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