Keto-Enol Tautomerism
An extensive introduction to keto-enol tautomerism in aldehydes and ketones, with mechanisms, quizzes, key concepts, references and more.
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Addition-Elimination Mechanisms With Neutral Nucleophiles (Including Acid Catalysis)
The Second-Most Important Mechanism In Carbonyl Chemistry – Carbonyl Elimination The reverse of nucleophilic addition to the C=O bond (giving a tetrahedral intermediate) is elimination
Read morePartial Charges Give Clues About Electron Flow
There’s a hidden layer of detail beneath chemical structures that students new to organic chemistry often miss. I’m talking about partial charges. Although each of
Read moreReactions of Enols – Acid-Catalyzed Aldol, Halogenation, and Mannich Reactions
Reactions of Enols – Aldol Condensation, Halogenation, Mannich Reaction In a previous post on keto-enol tautomerism, we described the keto and enol forms. In this
Read moreNucleophiles and Electrophiles
Nucleophiles and Electrophiles, Nucleophilicity and Electrophilicity All through the series on understanding where electrons are, and how they flow, we’ve been talking about how the
Read moreThe Three Classes of Nucleophiles
I know I’ve said this before, but a whole lot of organic chemistry can be boiled down to “nucleophile attacks electrophile“. A nucleophile is a
Read moreNucleophilicity vs. Basicity
Understanding The Differences Between Nucleophilicity vs Basicity Following up on Nucleophiles and Electrophiles, here’s a common question students have about nucleophilicity: 1. What’s the difference
Read moreCommon Blind Spot: Intramolecular Reactions
Intramolecular Reactions So I bought a belt today (pleather, 75 cents at the Goodwill). and decided to show it off. This is me putting it
Read moreReagent Friday: TsCl (p-toluenesulfonyl chloride) and MsCl (methanesulfonyl chloride)
TsCl (p-toluenesulfonyl chloride) And MsCl (methanesulfonylchloride) As Reagents In Organic Chemistry In a blatant plug for the Reagent Guide, each Friday I profile a different reagent
Read moreReagent Friday: NBS (N-Bromo Succinimide)
N-Bromosuccinimide (NBS) As A Reagent In Organic Chemistry In a blatant plug for the Reagent Guide, each Friday I profile a different reagent that is commonly
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