Understanding Electron Flow

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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An Arrow-Pushing Dilemma In Concerted Reactions

An Arrow-Pushing Dilemma In Concerted Reactions

April 5, 2013

Up to now, drawing out reaction mechanisms using the curved arrow formalism has been fairly straightforward. Yes, sometimes there is some ambiguity with respect to which carbon of a C-C π bond is forming a new bond …

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Alkene Addition Pattern #2: The “Three-Membered Ring” Pathway

Alkene Addition Pattern #2: The “Three-Membered Ring” Pathway

March 20, 2013

The “Three-Membered Ring” pathway In the last post we walked through a proposal for how the bromination of alkenes works and showed that it adequately explains many of the experimental observations made fo…

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Markovnikov’s Rule (2) – Why It Works

Markovnikov’s Rule (2) – Why It Works

February 11, 2013

Understanding Why Markovnikov’s Rule Works Let’s assemble all the facts we know about the reactions of alkenes with an acid like HCl so far. Regiochemistry: as we saw in the last post, reactions of alkenes…

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The E1 Reaction

The E1 Reaction

September 19, 2012

Last time in this walkthrough on elimination reactions, we talked about two types of elimination reactions. In this post, we’re going to dig a little bit deeper on one type of elimination reaction, and based on…

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The SN2 Mechanism

The SN2 Mechanism

July 4, 2012

Having gone through the two different types of substitution reactions, and talked about nucleophiles and electrophiles, we’re finally in a position to reveal the mechanism for one of the most important reactions…

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Two Types of Substitution Reactions

Two Types of Substitution Reactions

June 27, 2012

Chemistry is an experimental science. There is no great Ramanujan of our discipline, who, starting with a simple set of premises, could derive and predict all of the depth and variety of modern chemistry. No, it is mu…

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Leaving Groups Are Nucleophiles Acting In Reverse

Leaving Groups Are Nucleophiles Acting In Reverse

June 25, 2012

We’ve covered “what makes a good leaving group” before – the weaker the base, the better the leaving group. In this short post, I just want to make an observation. Note how similar nucleophiles…

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What Makes A Good Nucleophile?

What Makes A Good Nucleophile?

June 18, 2012

If you read the last post, you’ll recall that a nucleophile is a species that donates a pair of electrons to form a new covalent bond. Nucleophilicity is measured by comparing reaction rates; the faster the reac…

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Nucleophilicity vs. Basicity

Nucleophilicity vs. Basicity

June 6, 2012

Following up on Nucleophiles and Electrophiles, here’s a common question students have about nucleophilicity: What’s the difference between nucleophicity and basicity? Great, great question. First of all, …

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