My main goal at Master Organic Chemistry has always been to provide students with useful resources that they can't easily find anywhere else. About six months after I started tutoring organic chemistry, I realized that a lot of students had trouble keeping track of all the reagents in organic … [Read more...]
Reaction Friday: Keto-Enol Tautomerism
Today's Reaction Friday is all about keto-enol tautomersm, the chemistry equivalent of Jekyll and Hyde. Included: Tautomers are constitutional isomers (not resonance forms) The same factors which stabilize alkenes stabilize the enol form How to draw the mechanism for tautomerism (and how … [Read more...]
Reaction Friday – Fischer Esterification
The Fischer esterification is one of the most important reactions of carboxylic acids. Treatment of carboxylic acids with an alcohol in the presence of acid catalyst leads to the formation of esters, along with the elimination of a molecule of water. It therefore falls into the category of … [Read more...]
Reaction Friday – Reduction of Alkynes to Alkenes with Na/NH3
My apologies for the interruption. I seem to have wrested control of my blog back from the cats for now, but I'm not sure how long this will last. Clever little bugger. One thing I can say though - the cat picked a lot of questions to answer that I'd been ignoring because they seemed "dumb". A lot … [Read more...]
Reaction Friday: Conversion of Alcohols to Alkyl Chlorides With SOCl2
Treatment of alcohols with thionyl chloride (SOCl2) converts alcohols to alkyl chlorides. When the reaction is performed on secondary alcohols with a stereocenter, the reaction proceeds with inversion of configuration. … [Read more...]
Reaction Friday: Friedel Crafts Acylation
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's several different ways of showing how the acyl halide is activated by Lewis acid - … [Read more...]
Reaction Friday: Formation of Acetals from Ketones
Today's video is about the formation of acetals from aldehydes and ketones, an important method for the protection of the carbonyl group. One thing I forgot to mention in the video is that the reaction is an equilibrium - choosing alcohol as the solvent ensures that the equilibrium will be … [Read more...]
Reaction Friday: Addition of Grignard Reagents to Ketones
Grignard reagents are very useful carbon-based nucleophiles and will readily form carbon-carbon bonds with carbonyl compounds. Here the reaction of Grignard reagents with ketones is described, along with several examples and a detailed mechanism. Have a great weekend! … [Read more...]