New Textbook: Some Annotated Reaction Mechanisms
I’ve written an indexed catalogue of the reaction mechanisms I learned for my Organic Chemistry finals, which is now available on Amazon. These are mostly ‘named’ reactions, which I have annotated fairly thoroughly. This blog post is intended to share representative pages from the book to help you see if you want to buy it.
The front cover
The book’s main intention is to save students time. Independent learning should centre thinking about how and why reaction steps occur, rather than frantically googling to find the ‘correct’ mechanism for the Tsuji-Trost reaction. I hope it also has a secondary merit of modelling one way to set out answers to an organic mechanism exam questions; it took me a very long time to realise that annotation was something I was expected to do in exams, and I wish someone had helped me to see this sooner.
Representative Mechanisms
To give a small flavour of what a typical page looks like, some of the annotated reactions are presented below. The intention is to provide some justification for key moments in a reaction sequence.
A Hantzsch Pyrrole Synthesis
The Neber Rearrangement
The electrocyclic reactions of hexatrienes
The contrasting reactivity of stabilised and unstabilised sulphonium (sulfonium) ylids
The analogy between the Bayer-Villiger and Tiffaneau-Demjanov reactions
Representative Concepts
There is a brief discussion of a few key concepts at the start of the book. These are often related to organic applications of MO theory.
The ‘ate’ complex of silicon
The pi-orbitals of linear conjugated systems
Hyperconjugation in carbocations
Representative Navigation
The Table of Contents is intended to thematically group reactions in ways that reflect the broad shape of the exams that I sat (e.g. all the organometallic cycles are grouped together because there was typically a question on that topic). The index is intended to help students looking for a specific named reaction.
An excerpt from the Table of Contents
An excerpt from the index
Anticipated Reception
I’m not sure how the book will be received. It seems likely that students can readily access similar information using the internet, but at the same time internet sources often lack the justification for steps and can be incorrect.
It also seems likely that my organic education in 2007-10 won’t reflect the current education of many students today. Not every degree relies so heavily on named reactions as a training in Organic reasoning, for example. Nor is the book’s ambition to save students time so pressing in every curriculum.
I’m also acutely aware that some mechanisms are contested (I’ve only presented the radical DDQ oxidation, for example), and that I may - despite my best efforts - have made errors when presenting over two hundred mechanisms.
And yet I’ve written the book I wish I’d had when I was a student: a lean, dense collection of the things I didn’t know yet. As with my books on NMR, hypovalent clusters, and paramagnetism, I’m very open to to making edits. Get in touch if you see something I could improve!