Aromatic Reactions

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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Aromatic Synthesis (3) – Sulfonyl Blocking Groups

Aromatic Synthesis (3) – Sulfonyl Blocking Groups

November 26, 2018

I Just Want The ORTHO- Product, Thank You Question: Just how selective are ortho- para, directors for the ortho- and para- products, respectively? There are two ortho positions and one para. All else being equ…

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Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds

Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds

November 19, 2018

Let’s map out all of the reactions we’ve learned in this section on aromatic rings + substituents. Also included is a few reactions we actually haven’t covered yet – such as diazonium salt form…

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Aromatic Synthesis (2) – Polarity Reversal

Aromatic Synthesis (2) – Polarity Reversal

October 22, 2018

Quick summary: pay close attention to reactions that change ortho-, para- directors into meta- directors, and vice versa! Last time we talked about the importance of choosing the correct “order of operations&…

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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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