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JoVE Core Organic Chemistry Chapter 12.18: Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
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Organic Chemistry

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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
 
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JoVE Core Organic Chemistry Chapter 12.18: Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.

The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and the positively charged phosphorus atom in betaine undergo a ring-closure reaction to generate the four-membered oxaphosphetane ring.

Figure1

In some cases, a concerted [2 + 2] cycloaddition between the Wittig reagent and the carbonyl compound results in the oxaphosphetane intermediate.

Figure2

The unstable oxaphosphetane ring undergoes fragmentation to yield the desired alkene molecule along with a stable triphenylphosphine oxide as the by-product. The driving force for the Wittig reaction is the formation of a strong P=O bond in the phosphine oxide molecule.

Figure3

Tags

Wittig Reaction Aldehydes Ketones Alkenes Phosphorus Ylides Nucleophilic Addition Elimination Process Carbonyl Compound Phosphorus Ylide Betaine Oxaphosphetane Ring [2 + 2] Cycloaddition Alkene Molecule Triphenylphosphine Oxide P-O Bond

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