19.7b Wittig Reaction | Organic Chemistry

Chad provides a comprehensive lesson on the Wittig reaction (aka Wittig Alkene Synthesis), which converts ketones and aldehydes to alkenes. The entire Wittig reaction mechanism is covered both for the nucleophilic addition of triphenylphosphine, for the formation of the phosphoylide, and for the formation of the alkene. The Wittig reaction is also examined from the standpoint of retrosynthesis, to help you determine which side of the product alkene is more likely derived from a ketone/aldehyde and which side from the ylide (and ultimately an alkyl halide).
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00:00 Lesson Introduction
00:51 Introduction to the Wittig Reaction
03:57 Wittig Reaction Mechanism
06:47 Formation of Phosphoylides
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Пікірлер: 28

  • @ryanjeong6128
    @ryanjeong612811 ай бұрын

    Thank you Chad for organizing these videos in a simple and easy way to understand.

  • @ChadsPrep

    @ChadsPrep

    11 ай бұрын

    You're welcome - glad they are helpful.

  • @laura5878
    @laura5878 Жыл бұрын

    You're the oxygen to my phosphorus

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    😆😆😆

  • @breathbadminton
    @breathbadminton Жыл бұрын

    I love all your videos!!

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    Glad to hear it :) Happy studying!

  • @user-mf7pd1df4y
    @user-mf7pd1df4y7 ай бұрын

    thank you Chad! you are the besttt!!

  • @ChadsPrep

    @ChadsPrep

    7 ай бұрын

    Thank YOU!

  • @user-tu1fb1hr3u
    @user-tu1fb1hr3u2 ай бұрын

    Hi Chad , did you do a lesson on kinetic acidity and thermodynamic acidity ? Also on the enolate and enol?

  • @shinn-tyanwu4155
    @shinn-tyanwu41558 ай бұрын

    Clearly presented😊

  • @ChadsPrep

    @ChadsPrep

    8 ай бұрын

    Thanks!

  • @alaaammar4462
    @alaaammar4462 Жыл бұрын

    Hi can I ask why carboxylic has to be converted into esters during alkylation and wittig reaction please? Thank you.

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    Hey - is this in reference to something said in the video?

  • @alaaammar4462

    @alaaammar4462

    Жыл бұрын

    @@ChadsPrep Hi Mr Chad. No you didn't say that in the video. But I do always solve many organic questions and I've seen that carboxylic acid has been converted into esters during alkylation, wittig reaction and many other things. I'm not sure why?

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    Many strong nucleophiles are also strong bases and would be protonated in a protic solvent (think Grignard) let alone if you had an actual acid present. In the case of a carboxylic acid, you can convert it into an ester before reaction with certain nucleophiles and then convert it back to an acid afterwards. Otherwise, you might/would protonate the nucleophile at which point it would no longer be as strong a nucleophile (or even a nucleophile at all). Hope this helps!

  • @alaaammar4462

    @alaaammar4462

    Жыл бұрын

    @@ChadsPrep cheers Chad

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    @@alaaammar4462 👍

  • @Capt.DonSylvesteropele
    @Capt.DonSylvesteropele Жыл бұрын

    Great

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    Thank you

  • @maryamriaz6774
    @maryamriaz6774 Жыл бұрын

    Why strong base is used in this reaction?

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    Hey Marya, do you mean the ylide? We need a good nucleophile to attack the carbonyl carbon in which case. It is the nucleophillic qualities rather than basicity which is important.

  • @maryamriaz6774

    @maryamriaz6774

    Жыл бұрын

    ​@@ChadsPrep No Sir.i am talking when we form a ylide from alkyltriphosphonium salt then we use strong base to remove hydrogen from adjacent to phosphorus.

  • @ChadsPrep

    @ChadsPrep

    Жыл бұрын

    Maryam, note that the ylide is somewhat carbanion-like (look at one of its resonance structures). Carbanions are super strong bases themselves and it will require an even stronger base (BuLi) to deprotonate and form the ylide. If you look at butyl lithium it is even more carbanion-like which is why it is a stronger base than the ylide which is why it works here. For reference, the pKa of the conjugate acid of the ylide is ~35 whereas the pKa of butane (which is the conjugate acid of BuLi) is ~50. Hope this helps!

  • @maryamriaz6774

    @maryamriaz6774

    Жыл бұрын

    @@ChadsPrep okay accept my big thanks.

  • @fakhrulnawawi9681
    @fakhrulnawawi96813 жыл бұрын

    PPh3 is so bulky ..how it performed sn2?

  • @ChadsPrep

    @ChadsPrep

    3 жыл бұрын

    Hello fakhrul! You would think so, and if instead of phosphorous you put any element from the second period (like Nitrogen) with 3 phenyl groups attached and it would struggle to do backside attack. But the period 3 elements like phosphorus and sulfur have a much larger radius. For one this spreads out the phenyl groups farther from each other and farther from the side of the atom that will be attacking as a nucleophile. But it also results in them being much more polarizable. This means that their electron clouds are 'squishier' which allows them to change their shape to aid in nucleophilic attack. It might not be inuitive upon initial inspection but PPh3 is actually a pretty decent nucleophile. Hope this helps!

  • @fakhrulnawawi9681

    @fakhrulnawawi9681

    3 жыл бұрын

    @@ChadsPrep u means like more polarizable?

  • @NEET_ASPIRANT_2025_DR

    @NEET_ASPIRANT_2025_DR

    3 ай бұрын

    @@fakhrulnawawi9681 exactly