Aromatic Synthesis (1) – “Order Of Operations”

Aromatic Synthesis (1) – “Order Of Operations”

October 15, 2018

Up to now, we’ve covered electrophilic aromatic substitution [6 key reactions] [mechanism] [ortho-para-meta] and then the reactions of aromatic substituents [bromination & oxidation] [carbonyl reduction] [n…

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More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger

More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger

October 8, 2018

Quick summary of this post on three new reactions of aromatic substituents: reduction of nitro groups to amines, protection of amines as amides, and on the Baeyer-Villiger reaction of ketones: Three More Reactions Of …

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The Retro Diels-Alder Reaction

The Retro Diels-Alder Reaction

October 1, 2018

In the last post in this series on the Diels-Alder [See: Diels-Alder Reaction: Kinetic and Thermodynamic Control] we saw that if you apply enough heat,  the Diels-Alder can operate in both the forward and reverse dir…

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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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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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Classification of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers

Classification of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers

September 10, 2018

“How Are We Related, Again?”  A few weeks ago, at a family reunion in Ontario,  I introduced my relatives to the joy of liquid nitrogen ice cream. My cousins were there, as were many of their children. S…

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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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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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