Aromatic Reactions

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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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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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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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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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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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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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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