Organic Chemistry 2

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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Nucleophilic Aromatic Substitution (2) – Arynes

Nucleophilic Aromatic Substitution (2) – Arynes

September 17, 2018

Previously [see: Nucleophilic Aromatic Substitution] we saw that electron-poor aromatic rings containing a leaving group can undergo substitution with electron-rich nucleophiles.  We saw that the mechanism proceeds t…

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Diels-Alder Reaction: Kinetic and Thermodynamic Control

Diels-Alder Reaction: Kinetic and Thermodynamic Control

September 3, 2018

The Little Known Fact About Cyclopentadiene THEY Don’t Want You To Know About Let’s talk about cyclopentadiene, a commonly used diene for Diels-Alder reactions that, by the way, comes up all the time on te…

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The Wolff-Kishner, Clemmensen, And Other Sidechain Reductions

The Wolff-Kishner, Clemmensen, And Other Sidechain Reductions

August 27, 2018

The Great Friedel-Crafts Workaround A recent post covered oxidations on the “benzylic” carbon (i.e. on the carbon adjacent to the aromatic ring). We showed that benzylic C-H bonds are unusually weak, and c…

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Nucleophilic Aromatic Substitution (NAS)

Nucleophilic Aromatic Substitution (NAS)

August 20, 2018

Quick summary for this post: Not The Aromatic Substitution Reaction You Were Expecting Let’s review electrophilic aromatic substitution (EAS). What have we learned? The aromatic ring acts as a nucleophile, and a…

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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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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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