Dienes and MO Theory

Regioselectivity In The Diels-Alder Reaction

Regioselectivity In The Diels-Alder Reaction

November 5, 2018

The Diels-Alder is an onion, and we just keep peeling back the layers. Today’s post is about regioselectivity in the Diels-Alder. Quick summary: “Regioselectivity” In The Diels-Alder Reaction So far …

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The Retro Diels-Alder Reaction

The Retro Diels-Alder Reaction

October 1, 2018

In the last post in this series on the Diels-Alder [See: Diels-Alder Reaction: Kinetic and Thermodynamic Control] we saw that if you apply enough heat,  the Diels-Alder can operate in both the forward and reverse dir…

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The Cope Elimination

The Cope Elimination

September 24, 2018

The “Cope Elimination” is a reaction where an amine is oxidized to an intermediate called an “N-oxide”, which, when heated, acts as the base in an intramolecular elimination reaction. Treating …

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Diels-Alder Reaction: Kinetic and Thermodynamic Control

Diels-Alder Reaction: Kinetic and Thermodynamic Control

September 3, 2018

The Little Known Fact About Cyclopentadiene THEY Don’t Want You To Know About Let’s talk about cyclopentadiene, a commonly used diene for Diels-Alder reactions that, by the way, comes up all the time on te…

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Why Are Endo Products Favored in the Diels-Alder Reaction?

May 11, 2018

[Advanced] Secondary Orbital Interactions – A Rationale For Why Endo Products Are Favored   In our last post, we noted that endo products tend to be favored over exo products in the Diels-Alder reaction.…

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Molecular Orbitals in the Diels Alder Reaction

Molecular Orbitals in the Diels Alder Reaction

March 23, 2018

Today we’re going to go into the mechanism of the Diels-Alder reaction from a molecular orbital perspective. Let’s recap where we are with the Diels-Alder so far: The Diels-Alder reaction combines a diene …

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Exo vs Endo Products In The Diels Alder: How To Tell Them Apart

February 9, 2018

Today we’ll cover how to tell endo– and exo- products apart in the Diels-Alder reaction. Shortcut below.  For the long winded walkthrough with lots of examples, read the post. Exo and Endo Products in…

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Stereochemistry of the Diels-Alder Reaction

Stereochemistry of the Diels-Alder Reaction

November 13, 2017

Here’s what we’ve learned about the Diels Alder reaction so far: [previous post in this series] 3 pi bonds are always broken 2 sigma bonds and a pi bond are always formed, resulting in a new six-membered r…

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Cyclic Dienes and Dienophiles in the Diels-Alder Reaction

Cyclic Dienes and Dienophiles in the Diels-Alder Reaction

September 8, 2017

Last post in this series we introduced the Diels-Alder reaction. We saw that no matter how complex the diene or dienophile, or no matter what substituents are attached, the pattern of bonds that form and break are alw…

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The Diels-Alder Reaction

The Diels-Alder Reaction

August 30, 2017

Today we’ll introduce  a reaction I consider to be the most useful and powerful reaction in all of organic chemistry: the Diels-Alder reaction. But don’t take some random blogger’s word for it. Her…

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