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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Reactions on the “Benzylic” Carbon: Bromination And Oxidation

Reactions on the “Benzylic” Carbon: Bromination And Oxidation

June 13, 2018

Today we’ll be going through two reactions on alkyl groups adjacent to aromatic rings: benzylic bromination and benzylic oxidation. Here’s the quick summary: Alkyl Groups = Roughage In nutrition, “ro…

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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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Intramolecular Friedel-Crafts Reactions

Intramolecular Friedel-Crafts Reactions

May 30, 2018

Intramolecular Reactions Here is an instant formula for an organic chemistry exam question. Start with a straightforward reaction that students understand fairly well,  like the Williamson Ether synthesis…. (dr…

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Electrophilic Aromatic Substitution Reactions (3) – Friedel Crafts Alkylation and Acylation

Electrophilic Aromatic Substitution Reactions (3) – Friedel Crafts Alkylation and Acylation

May 17, 2018

Today’s post is on the Friedel-Crafts alkylation and acylation reactions. Quick summary: This is the third in a series of three posts on the key electrophilic aromatic substitution (EAS) reactions in introductor…

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Why Are Endo Products Favored in the Diels-Alder Reaction?

May 11, 2018

[Advanced] Secondary Orbital Interactions – A Rationale For Why Endo Products Are Favored   In our last post, we noted that endo products tend to be favored over exo products in the Diels-Alder reaction.…

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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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Electrophilic Aromatic Substitutions (2) – Nitration and Sulfonylation

Electrophilic Aromatic Substitutions (2) – Nitration and Sulfonylation

April 30, 2018

Today’s topic: nitration and sulfonylation of benzene: In the previous post on halogenation via electrophilic aromatic substitution, we saw that this electrophilic aromatic substitution reaction proceeded in thr…

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Reactions of Sugars: Glycosylation and Protection

April 24, 2018

If reactions are the meat of an organic chemistry course, then nomenclature is the bun – and you’d be forgiven for thinking that the content in this chapter on sugars has been a little, er, “carb-hea…

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Electrophilic Aromatic Substitutions (1) – Halogenation

Electrophilic Aromatic Substitutions (1) – Halogenation

April 18, 2018

Now that we’ve spent ample time digging into the mechanism of electrophilic aromatic substitution,  activating and deactivating groups, and ortho- ,para– and meta– directors, we’re finally rea…

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