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Lecture 18 Diels–Alder
Summary
Here is the lecture in a minute
- 1Endo wins because it is the kinetic product
- 2The diene only reacts from its s-cis conformation
- 3Heat reverses it, cold locks the endo adduct in
@Lecture 18 Diels–Alder
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Why is endo the major product?
It is the kinetic product. Secondary orbital overlap wins cold.
Lecture 18 · 31:20Clayden ch.35
Recall
Flashcards
Diels–Alder Reactions
2 of 5
What conformation must the diene adopt?
s-cis. A diene locked s-trans cannot react, because its termini can’t reach the dienophile at once.
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Diels–Alder Reactions
Question 1 of 3
Why does a diene locked in the s-trans conformation fail to react?
Its termini cannot reach the dienophile at once
It has no π electrons to donate
It is too electron-poor to act as a diene
Correct. Only s-cis puts C1 and C4 close enough to bond at the same time.
On the walk home
Podcast recaps
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