Waves of publishers reps, with regional sales managers in tow, have washed up on my office doorstep in the last ten days. With the current textbook edition cycle being about three years it seems that we are always reviewing texts. Other than the time cost, I don't mind this.
I have a collection of organic texts that goes back to the 1870s. I even have the original hand written 1878 class notes of a UC Berkeley student. From this perspective, the teaching of organic really has not changed that much except for the gradual introduction of spectroscopy and physical organic and mechanism into the subject. In many respects the vast majority of textbooks are still teaching the modern equivalent of Type Theory.
For those who don't know, from the late 1820's there was the Theory of Radicals in which there were fragments which were interchangeable on a center. This is where the use of R to represent some undefined carbon chain comes from. Type Theory developed in the late 1840s and early 1850s and followed the Theory of Radicals. I think it was Gerhardt who pushed the idea of Type Theory starting with the Water Type. Alcohols and Ethers are water types, in which the hydrogens are replaced by "radicals"(R groups). Hoffmann later developed the Ammonia Type to discuss what we know as amines.
Anyway, to ask the question that was on mind when I began, if you could start from scratch in creating an organic textbook, how would you organize it? Don't worry about the marketplace. I want to know what your perfect text organization would look like. I don't care about the format of being an e-book or distribution on rolls of toilet paper, it's the content that I am asking about. Textbook price does not matter for this discussion, so please let's not go there.
My mechanism bias comes out in my thoughts about this. After the basics of what organic molecules are, I would start with physical properties ending the section with solubility. Then I would move from water solubility to pH and pKa and then to reactivity starting with the systems with the greatest bond polarity. I would leave the less reactive hydrocarbon systems to the end of the course.
My logic is that if students can appreciate the chemistry of a polar system like a carbonyl first, when one goes to alkene, allyl, or even aromatic systems they can see that the fundamental reactions are the same, with the added wrinkle that you no longer have the same level of bond polarization.
I am curious to know what others would do if they could create their own book just by thinking about it.
T.S. Hall
The Bluing of Red Rocks Amphitheater
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