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Wittig Reaction definitions

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  • Wittig Reaction
    A transformation forming regiospecific alkenes by reacting a carbonyl compound with an ylide, allowing precise placement of R groups.
  • Alkene
    A hydrocarbon product with a carbon-carbon double bond, formed regiospecifically in this reaction from aldehydes or ketones.
  • Ylide
    A neutral molecule with adjacent positive and negative charges, typically featuring phosphorus and carbon, crucial for this reaction.
  • Carbonyl Compound
    A molecule containing a C=O group, such as an aldehyde or ketone, serving as a key reactant in this transformation.
  • Triphenylphosphine
    A phosphorus compound with three phenyl groups, used to generate the ylide via SN2 reaction with an alkyl halide.
  • Alkyl Halide
    An organic molecule containing a halogen atom bonded to an alkyl group, serving as a precursor for ylide formation.
  • Butyllithium
    A strong organometallic base, commonly used to deprotonate the phosphorus compound, enabling ylide formation.
  • SN2 Reaction
    A bimolecular nucleophilic substitution mechanism, essential for forming the phosphorus-carbon bond in ylide synthesis.
  • Betaine
    A tetrahedral intermediate with non-adjacent charges, formed after nucleophilic addition of the ylide to the carbonyl.
  • Oxaphosphetane
    A four-membered ring intermediate containing phosphorus and oxygen, formed during the rearrangement step before alkene formation.
  • Regiospecificity
    The property allowing precise control over the position of substituents on the newly formed alkene.
  • Stereoisomer
    A molecule differing in spatial arrangement, such as E and Z forms, which may both result since this reaction is not stereospecific.
  • Nucleophilic Addition
    A step where a nucleophile attacks an electrophilic carbon, leading to the formation of a tetrahedral intermediate.
  • Resonance Structure
    Alternative Lewis structures representing electron delocalization, important for depicting ylide and intermediate stability.
  • Organometallic Compound
    A molecule containing a metal-carbon bond, such as butyllithium, often used as a strong base in organic synthesis.