nucleophiles

Comparing the SN1 and SN2 Reactions

Comparing the SN1 and SN2 Reactions

August 8, 2012

Hey! You can now download a free 1-page Summary Sheet of SN1 vs SN2 reactions containing all the material on this series of blog posts here: Download SN1 vs SN2 Summary Sheet PDF   Since we’ve gone through …

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The Conjugate Acid Is A Better Leaving Group

The Conjugate Acid Is A Better Leaving Group

August 7, 2012

One of the key factors that determines whether a nucleophilic substitution reaction will happen or not is the identity of the leaving group. Previously, we’ve seen that good leaving groups are weak bases. That m…

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Why the SN2 Reaction Is Powerful

Why the SN2 Reaction Is Powerful

July 11, 2012

Having gone through the mechanism of the SN2 reaction, let’s take a second and look at why it might be useful. In nucleophilic substitution reactions, we’re trading a carbon-(leaving group) bond for a carb…

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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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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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Nucleophiles and Electrophiles

Nucleophiles and Electrophiles

June 5, 2012

All through the series on understanding where electrons are, and how they flow, we’ve been talking about how the basis of chemistry is that opposite charges attract and like charges repel, and that in reactions,…

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Acid Base Reactions: What’s the Point?

Acid Base Reactions: What’s the Point?

May 30, 2012

One thing has been missing from our discussion of acid-base reactions. Who cares? What does it matter that we understand acid base reactions? Why is it important? Today, I hope to show that it matters a lot, not only …

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Polar Protic? Polar Aprotic? Nonpolar? All About Solvents

Polar Protic? Polar Aprotic? Nonpolar? All About Solvents

April 27, 2012

A lot of students I talk to have questions about solvents, so I’ve decided to put together a reference post on them. Solvents can cause considerable confusion in reactions, because they’re listed along wit…

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