Amines

The Hofmann and Curtius Rearrangements

The Hofmann and Curtius Rearrangements

September 19, 2017

Here’s the thing about the coverage of “amines” in Org 2: there’s no narrative. Unlike most chapters, it doesn’t start with a set of concepts and then build up to a series of examples you apply t…

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Reductive Amination

Reductive Amination

September 1, 2017

Reminder: Alkylation of Amines Is Rarely The Answer OK – so making amines through direct alkylation is generally not a great way to go. You could even say it’s crappy. What’s the “right” …

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Alkylation of Amines Tends To Be A Pretty Crappy Reaction

Alkylation of Amines Tends To Be A Pretty Crappy Reaction

May 26, 2017

Trends in the basicity of amines provide a classic example of why chemistry is so interesting; it’s deciphering the delicate trade-offs between various general factors in specific cases that gives chemists a buz…

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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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Basicity of Amines And pKaH

Basicity of Amines And pKaH

April 18, 2017

How do you measure the basicity of an amine? Case in point: what’s a stronger base: pyridine or piperidine? Care to make a prediction? If you said piperidine, congratulations – it is indeed a stronger bas…

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Carbonyl Mechanisms: Neutral Nucleophiles, Part 1

Carbonyl Mechanisms: Neutral Nucleophiles, Part 1

May 10, 2010

Today, building on the previous 2-part series on mechanisms of anionic nucleophiles in carbonyl chemistry, I’m going to start looking at the reactions of the neutral nucleophiles: water, alcohols, amines, enols …

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Summary Sheet #3: Reactions of Carbonyls – The Big Picture

April 23, 2010

The reason why I harp on organic chemistry as boiling down to “nucleophile attacks electrophile” is because it’s a greatly simplifying way to look at chemical reactions. After you’ve done organ…

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