Amines

Reactions of Diazonium Salts: Sandmeyer and Related Reactions

Reactions of Diazonium Salts: Sandmeyer and Related Reactions

December 3, 2018

Formation of Diazonium Salts From Aromatic Amines Today let’s talk about a set of reactions of aromatic amines, that variously are catalogued under “amines” and “aromatic compounds”, depe…

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The Strecker Synthesis of Amino Acids

The Strecker Synthesis of Amino Acids

November 12, 2018

What’s not to love about the cyanide ion? OK, OK, it’s a deadly poison, and should be treated extremely carefully in the lab. But besides that, it’s an excellent nucleophile that can react with a wi…

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The Cope Elimination

The Cope Elimination

September 24, 2018

The “Cope Elimination” is a reaction where an amine is oxidized to an intermediate called an “N-oxide”, which, when heated, acts as the base in an intramolecular elimination reaction. Treating …

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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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