aromaticity

Frost Circles

Frost Circles

May 17, 2017

We’ve spent a lot of time in previous posts “building up” and drawing out the molecular orbitals for various species. In this post we’ll learn an extremely useful shortcut that will help us dra…

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The Pi Molecular Orbitals of Benzene

The Pi Molecular Orbitals of Benzene

May 5, 2017

Today, let’s go through how to draw out the molecular orbitals of benzene. We’ll compare them with the molecular orbitals for (linear) hexatriene. The big takeaway is that from contrasting the molecular o…

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Antiaromaticity

March 27, 2017

Here’s a quick summary for today’s post, which concerns a very interesting (and rare) property of certain molecules called “anti-aromaticity”. In our previous posts in our series on aromaticity…

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“Is This Molecule Aromatic?” Some Practice Problems

“Is This Molecule Aromatic?” Some Practice Problems

March 3, 2017

Our last post in this series on aromaticity went through the 4 conditions a molecule must fulfill in order to be aromatic. First, it must be cyclic Second, every atom around the ring must have an available p-orbital T…

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Rules For Aromaticity

Rules For Aromaticity

February 23, 2017

In the last post we introduced the concept of aromaticity, a property of some unusually stable organic molecules such as benzene. Although some aromatic molecules are indeed fragrant (hello, vanillin! ) the term &#…

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Introduction To Aromaticity

Introduction To Aromaticity

January 20, 2017

The Highly Anomalous Behavior of “Cyclohexatriene” Scene: a plane full of passengers are flying over the Atlantic ocean. Halfway through the flight, there’s suddenly a loud THUNK from outside t…

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Khan Academy for Organic Chemistry – Part 5

Khan Academy for Organic Chemistry – Part 5

October 23, 2012

IN this post (the 5th of 6) we go through videos 52-64 of Khan Academy for Organic Chemistry, covering mostly aromatic compounds and aldehydes/ketones. [For previous posts, see Part 1, Part 2, Part 3, Part 4] Video #5…

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What does 4n+2 mean?

What does 4n+2 mean?

June 29, 2012

The other night a student came to me with a question about aromaticity. “There’s one thing I don’t get”, she said. “They say a molecule has to have 4n+2 electrons. How do you find n?̶…

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7 Factors That Stabilize Positive Charge in Organic Chemistry

7 Factors That Stabilize Positive Charge in Organic Chemistry

March 7, 2012

Just to clarify: make sure you’re familiar with how formal charge can lie before you read this. These factors determine the stability of “true” positive charges (i.e. low electron densities), not …

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Reaction Friday: Friedel Crafts Acylation

Reaction Friday: Friedel Crafts Acylation

March 2, 2012

Today’s Reaction Friday is about the Friedel Crafts acylation of benzene and other aromatics, an important example of electrophilic aromatic substitution. One thing I forgot to say at the bottom is that there…

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