resonance

Activating and Deactivating Groups In Electrophilic Aromatic Substitution

Activating and Deactivating Groups In Electrophilic Aromatic Substitution

September 26, 2017

Quick summary on what we’ll talk about today, on activating and deactivating groups in electrophilic aromatic substitution: There’s a lot to this post, so here’s a quick index: Electrophilic Aromatic…

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The Mesomeric Effect And Aromatic Amines

April 28, 2017

We’ve seen that several key factors influence the basicity of amines – charge, resonance, inductive effects, pi donor / pi acceptor behavior, hybridization and even the contribution of the nitrogen lone pa…

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5 Factors That Affect Basicity of Amines

5 Factors That Affect Basicity of Amines

April 26, 2017

What are the most important factors that affect the basicity of amines? Previously, we’ve seen how to evaluate the basicity of amines by examining the pKa of its conjugate acid (pKaH). (The higher the pKaH, th…

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Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion

Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion

February 16, 2017

In the last post, we showed how to build a molecular orbital (MO) diagram for a typical C-C pi bond. We saw that: The number of molecular orbitals equalled the number of contributing atomic orbitals. The overlap of …

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Conjugation and Resonance

Conjugation and Resonance

January 24, 2017

On Conjugation And Resonance This is the first in a series of posts that will eventually cover conjugation, pi systems, molecular orbital theory, dienes, 1,2- and 1,4- additions, the Diels Alder reaction and other per…

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Alcohols (3) – Acidity and Basicity

Alcohols (3) – Acidity and Basicity

October 17, 2014

In the last post we said that one of the keys to the reactions of alcohols as we go forward is that the conjugate acid is a better leaving group and the conjugate base is a better nucleophile. We might have gotten a …

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Crash Course On Resonance

Crash Course On Resonance

March 13, 2014

Note – the Crash Course on Resonance is now part of Master Organic Chemistry Elite – Learn more here One extremely common type of email I get from students goes like this: “I feel way behind on [X] …

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3 Factors That Stabilize Free Radicals

3 Factors That Stabilize Free Radicals

August 2, 2013

In the last post we introduced free radicals – neutral, electron-deficient chemical species with a partially filled orbital – and learned that they are highly reactive intermediates in organic chemistry. …

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Rearrangement Reactions (1) – Hydride Shifts

Rearrangement Reactions (1) – Hydride Shifts

August 15, 2012

For nucleophilic substitution, the pattern of bonds that form and break is pretty straightforward. You break C-(leaving group) and you form C-(nucleophile). A straight swap. But every once in awhile you might see a &…

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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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