Master Organic Chemistry

Introducing the Reaction Guide

October 17, 2012 By James Ashenhurst Leave a Comment

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...]

Filed Under: Organic Chemistry 1, Organic Chemistry 2, Organic Reactions Tagged With: Reaction Friday, reaction guide, reactions

Reaction Friday: Keto-Enol Tautomerism

April 27, 2012 By James Ashenhurst 5 Comments

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...]

Filed Under: Alkenes, Ketones, Organic Chemistry 2, Organic Reactions Tagged With: enols, ketones, Reaction Friday, tautomerism, video

Reaction Friday – Fischer Esterification

April 14, 2012 By James Ashenhurst 2 Comments

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...]

Filed Under: Alcohols, Carboxylic acids, Organic Chemistry 2, Organic Reactions Tagged With: acid catalyst, alcohols, esters, fischer esterification, Reaction Friday

Reaction Friday – Reduction of Alkynes to Alkenes with Na/NH3

April 6, 2012 By James Ashenhurst 9 Comments

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...]

Filed Under: Alkenes, Alkynes, Organic Chemistry 1, Organic Reactions Tagged With: alkenes, alkynes, Na, NH3, Reaction Friday, reduction, sodium, stereoselective, trans

Reaction Friday: Conversion of Alcohols to Alkyl Chlorides With SOCl2

March 10, 2012 By James Ashenhurst 4 Comments

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...]

Filed Under: Alcohols, Alkyl Halides, Organic Chemistry 2, Organic Reagents Tagged With: Reaction Friday, reaction guide, reagents, socl2, thionyl chloride

Reaction Friday: Friedel Crafts Acylation

March 2, 2012 By James Ashenhurst 10 Comments

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...]

Filed Under: Organic Chemistry 2, Organic Reactions Tagged With: acid halides, acyl halides, AlCl3, aromaticity, aromatics, benzene, electrophiles, electrophilic aromatic substitution, FeCl3, Friedel-Crafts, mechanisms, Reaction Friday

Reaction Friday: Formation of Acetals from Ketones

February 24, 2012 By James Ashenhurst 2 Comments

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 driven … [Read more...]

Filed Under: Aldehydes, Ketones, Organic Chemistry 2, Organic Reactions Tagged With: acetals, alcohols, aldehydes, ketones, mechanism, Reaction Friday, video

Reaction Friday: Addition of Grignard Reagents to Ketones

February 18, 2012 By James Ashenhurst 6 Comments

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...]

Filed Under: Alcohols, Ketones, Organic Chemistry 2, Organic Reactions Tagged With: alcohols, grignard reagents, ketones, mechanisms, nucleophiles, organometallics, Reaction Friday

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