Reductive Amination
…used as well. It’s possible to start with a primary amine and do two successive reductive aminations, obtaining a tertiary amine. Reductive amination does not work for forming bonds from…
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Reactions of Dienes: 1,2 and 1,4 Addition
…will not always be true for all dienes!! Here are three examples that will help you think through the main issues (answers in the next post). 12. Other Reactions Can…
Read moreConversion of acid chlorides to esters through addition of an alcohol
…2500 quizzes, the Reaction Encyclopedia, Org 1 / Org 2 summary sheets, and flashcards, sign up here for only 30 cents/ day! Real-World Examples: Org. Synth. 1932, 12, 1 DOI…
Read moreIntramolecular Friedel-Crafts Reactions
…still works. Why are intramolecular reactions good exam questions? Because they sort out the students who learn the reactions by memorizing a table of simple examples, and those who actually…
Read moreNucleophilic Aromatic Substitution (NAS)
…generally not energetically favorable, this is compensated by the fact that it restores aromaticity. [UPDATE: In the comments, Matt brings up a very interesting recent study that suggests that some…
Read moreAlkylation of Amines (Sucks!)
…The best example of this is with methyl iodide, in a reaction called exhaustive methylation. Recall that methyl halides are the fastest-reacting alkyl halides in SN2 reactions due to their…
Read moreEAS Reactions (3) – Friedel-Crafts Acylation and Friedel-Crafts Alkylation
…chloride (AlCl3) is often used, but FeCl3 and other Lewis acids will also do the job. Here’s a general example of the Friedel-Crafts acylation: A specific example is the reaction…
Read moreAssigning Cahn-Ingold-Prelog (CIP) Priorities (2) – The Method of Dots
…Centers, Multiple Bonds, And Isotopes? This post is about some of the further complications we see in assigning priorities. For example, how do you assign priorities in the following cases:…
Read moreNucleophilicity of Amines
…this comes up is that nucleophilicity is much more sensitive to steric effects than is acidity/basicity. For example, t-butylamine is about as basic as other primary amines but is considerably…
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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