Formation of Diazonium Salts from Aromatic Amines
Description: Treatment of aromatic amines with acid and nitrous acid (or NaNO2) leads to the formation of diazonium salts. The rest of this page is available to MOC Members only….
Read moreMaster Organic Chemistry Reaction Guide
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The Hofmann and Curtius Rearrangements
…family of rearrangement reactions that share a common mechanistic step. [as do the Beckmann and Wolff rearrangements – see bonus topic 2] In the Hofmann rearrangement, an amide is treated…
Read moreBirch Reduction
…this is not a Birch reduction – this is elimination of a chloride to form benzyne followed by attack! Another common mistake is to imagine that the role of Na…
Read moreThe Hofmann Elimination
…to amines. 3. The “Hofmann Degradation” Back in 1851, not many techniques for analyzing complex molecules were available. One method for determining the structure of an unknown compound was to…
Read moreFormation of amides from acid chlorides and amines
Description: Addition of primary or secondary amines (or ammonia) to acid chlorides results in amides. The rest of this page is available to MOC Members only. To get access to…
Read moreMore Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger
…References and Further Reading Baeyer-Villiger oxidation: Einwirkung des Caro’schen Reagens auf Ketone Adolf von Baeyer, Victor Villiger Ber. 1899, 32 (3), 3625 DOI: 10.1002/cber.189903203151 This paper by Nobel Laureate Adolf…
Read moreThe Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions
…formation and reduction But first: why might you want to do this? Well, it’s a key component in a common little synthesis problem I like to call “The Great Friedel-Crafts…
Read moreNucleophilic Aromatic Substitution (2) – The Benzyne Mechanism
…and completely independently of, the aromatic pi system). Since these orbitals actually point away from each other, the overlap between them is poor, resulting in a “triple bond” that is…
Read moreDecarboxylation of beta-keto carboxylic acids
…cents/ day! Real-World Examples Org. Synth. 1927, 7, 40 DOI Link: 10.15227/orgsyn.007.0040 Click to Flip Org. Synth. 1934, 14, 58 DOI Link: 10.15227/orgsyn.014.0058 Click to Flip Org. Synth. 1941, 21,…
Read moreAssigning Cahn-Ingold-Prelog (CIP) Priorities (2) – The Method of Dots
…each atom I am comparing, which is why I call this The Method of Dots). Compare each list, atom by atom. The t-butyl (C(CH3)3) group has the highest priority [C,C,C…
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