Amines

Some Reactions of Azides

Some Reactions of Azides

June 29, 2018

The azide ion (N3– ) is one of those chemical entities that just plain looks weird.  Three nitrogens in a row? check Two negative charges and a positive charge, for a net charge of –1 ? check Stable? check …

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Protecting Groups for Amines – Carbamates

Protecting Groups for Amines – Carbamates

June 7, 2018

An Introduction To Simple Peptide Synthesis In a recent post [Amides: Synthesis, Properties, and Nomenclature] we went through 3 common ways of making amides: Adding amines to acyl halides / anhydrides Partial hydroly…

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Nucleophilicity of Amines

Nucleophilicity of Amines

May 7, 2018

Bonus Topic – Nucleophilicity Of Amines The relative nucleophilicity of amines doesn’t get a  lot of coverage (translation: doesn’t get tested) in many organic chemistry courses, but if we’re going to…

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Amides: Properties, Synthesis, and Nomenclature

Amides: Properties, Synthesis, and Nomenclature

February 28, 2018

In this post, we’ll try to provide a broad overview of amides.  We’ll provide a brief overview of amide nomenclature, two important properties of amides that differ greatly from amines, and go over three …

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The Gabriel Synthesis

The Gabriel Synthesis

January 31, 2018

We’ve seen previously that it’s hard to *usefully* build amines through the SN2 reaction, because once amines start reacting with alkyl halides, the products tend to be more nucleophilic than the reactants…

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The Hofmann Elimination

The Hofmann Elimination

October 18, 2017

The Hofmann Elimination is an elimination reaction that forms C-C double (pi) bonds that specifically occurs when the leaving group is NR3 [note] It proceeds through an E2 mechanism. Although the key concepts are no …

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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 Is A Shite Reaction

Alkylation of Amines Is A Shite 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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