Dienes and MO Theory

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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s-cis and s-trans

s-cis and s-trans

May 12, 2017

s-cis and s-trans. What does those terms mean? Recall cis and trans. The reason Aldrich Chemical Co. can sell 99% cis-2-butene and 99% trans-2-butene in separate bottles is because of restricted rotation about the …

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More On 1,2 and 1,4 Additions To Dienes

More On 1,2 and 1,4 Additions To Dienes

April 11, 2017

In the last post we covered 1,2 and 1,4 additions to dienes, specifically the addition of strong acid (e.g. HCl or HBr) to dienes. To recap: In Org 1 we learned that addition of HCl and HBr to normal, isolated alkenes…

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