Friedel-Crafts

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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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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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 Substitution: Introduction

Electrophilic Aromatic Substitution: Introduction

July 11, 2017

Today’s post covers a key reaction of aromatic compounds: electrophilic aromatic substitution. When we covered the reactions of alkenes a while back – a lot of reactions! –  we saw that the vast maj…

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Reaction Friday: Friedel Crafts Acylation

Reaction Friday: Friedel Crafts Acylation

March 2, 2012

Today’s Reaction Friday is about the Friedel Crafts acylation of benzene and other aromatics, an important example of electrophilic aromatic substitution. One thing I forgot to say at the bottom is that there…

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The Lies We Tell

The Lies We Tell

August 10, 2011

Zed Shaw teaches a course in writing Python called “Python the Hard Way“. Because the hard way is easier, he says. In the end, he’s right. If you really want to learn organic chemistry, the hard way …

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Reagent Friday: Aluminum Chloride (AlCl3)

Reagent Friday: Aluminum Chloride (AlCl3)

July 22, 2011

In a blatant plug for the Reagent Guide, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  Note: there’s going to be an exciting announcement within the next little whi…

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Common Blind Spot: Intramolecular Reactions

Common Blind Spot: Intramolecular Reactions

July 4, 2011

So I bought a belt today (pleather, 75 cents at the Goodwill).  and decided to show it off. This is me putting it together. This is what it looks like now: At this point you’re probably saying WTF: that’s…

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