The 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…
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Conversion of carboxylic acids into acid chlorides with SOCl2
Description: Thionyl chloride converts carboxylic acids into acid chlorides. The reaction liberates HCl and SO2 gas. The rest of this page is available to MOC Members only. To get access…
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 moreConversion of acid chlorides to aldehydes using LiAlH(O-tBu)3
Description: Addition of the bulky reducing agent lithium tri-t-butoxy aluminum hydride [LiAlH(O-tBu)3] to acid chlorides results in the formation of aldehydes. The rest of this page is available to MOC…
Read moreClemmensen Reduction of Ketones/Aldehydes to Alkanes
Description: Addition of zinc amalgam, Zn(Hg) and acid to a ketone results in an alkane. This is called the Clemmensen reduction. The rest of this page is available to MOC…
Read moreClaisen Condensation of esters
Description: When esters are treated with strong base, an enolate can be formed. The resulting enolate can add to another ester, resulting in a substitution at the carbonyl carbon. The…
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…
Read moreElectrophilic Aromatic Substitutions (2) – Nitration and Sulfonation
…giant in computational Physical Organic chemistry. This is a computational study of aromatic sulfonation that attempts to clarify the mechanism. Computational modeling shows that a trimolecular reaction with 2 SO3…
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Read moreBromination of Aromatics to give Bromoarenes
…17, 23 DOI Link: 10.15227/orgsyn.017.0023 Click to Flip Org. Synth. 1951, 31, 29 DOI Link: 10.15227/orgsyn.031.0029 Click to Flip Org. Synth. 1960, 40, 7 DOI Link: 10.15227/orgsyn.040.0007 Click to Flip…
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