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
Thank you Chad for organizing these videos in a simple and easy way to understand.
@ChadsPrep
11 ай бұрын
You're welcome - glad they are helpful.
You're the oxygen to my phosphorus
@ChadsPrep
Жыл бұрын
😆😆😆
I love all your videos!!
@ChadsPrep
Жыл бұрын
Glad to hear it :) Happy studying!
thank you Chad! you are the besttt!!
@ChadsPrep
7 ай бұрын
Thank YOU!
Hi Chad , did you do a lesson on kinetic acidity and thermodynamic acidity ? Also on the enolate and enol?
Clearly presented😊
@ChadsPrep
8 ай бұрын
Thanks!
Hi can I ask why carboxylic has to be converted into esters during alkylation and wittig reaction please? Thank you.
@ChadsPrep
Жыл бұрын
Hey - is this in reference to something said in the video?
@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
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
Жыл бұрын
@@ChadsPrep cheers Chad
@ChadsPrep
Жыл бұрын
@@alaaammar4462 👍
Great
@ChadsPrep
Жыл бұрын
Thank you
Why strong base is used in this reaction?
@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
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
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
Жыл бұрын
@@ChadsPrep okay accept my big thanks.
PPh3 is so bulky ..how it performed sn2?
@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
3 жыл бұрын
@@ChadsPrep u means like more polarizable?
@NEET_ASPIRANT_2025_DR
3 ай бұрын
@@fakhrulnawawi9681 exactly