Master Organic Chemistry

Reactions on the “Benzylic” Carbon: Bromination And Oxidation

June 13, 2018 By James Ashenhurst 6 Comments

The carbon adjacent to an aromatic ring - the "benzylic" carbon -  can participate in several useful and interesting reactions. Today we'll provide examples and mechanisms for two key examples: benzylic bromination and benzylic oxidation. Here's the quick summary: Alkyl Groups = Roughage In … [Read more...]

Filed Under: Aromatic Reactions Tagged With: aromatic synthesis, benzylic bromination, benzylic oxidation, br2, kmno4, NBS, radical stability

Bonus Topic: Allylic Rearrangements

December 2, 2013 By James Ashenhurst 10 Comments

In this series on free radical reactions we've mostly covered the basics. In this post (and the next one) we're going to go into a little bit more detail on certain topics that until now I haven't had time to dive into.  Today's topic flows right from the subject of the last post, on allylic … [Read more...]

Filed Under: Alkenes, Organic Chemistry 1 Tagged With: allylic bromination, allylic rearrangement, bromination, NBS

Allylic Bromination

November 25, 2013 By James Ashenhurst 13 Comments

In previous posts on radicals, we've seen how bromine can selectively react with tertiary C-H bonds (bond strength 93 kcal/mol) over secondary (96 kcal/mol) and primary (100 kcal/mol) C–H bonds.  If you recall that bond dissociation energies are a good guide for predicting radical stability, then … [Read more...]

Filed Under: Alkenes, Organic Chemistry 1 Tagged With: allylic bromination, initiation, NBS, propagation, radicals, termination

Reagent Friday: NBS (N-Bromo Succinimide)

June 10, 2011 By James Ashenhurst 12 Comments

In a blatant plug for the Reagent Guide, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  If you've ever had the "pleasure" of working with bromine (Br2), you'll know that this dense orange liquid is a pain in the butt for two reasons.  First of all, it … [Read more...]

Filed Under: Alkenes, Alkyl Halides, Organic Chemistry 1, Organic Reagents Tagged With: allylic bromination, bromine, electrophiles, halogens, NBS, radicals, reagent friday, reagents, reagents app

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