The first time I taught out of Joel’s text, I had no idea where I was going to put the semester break. I enjoyed how well each chapter flowed into the next, but that left me wondering where to put a five-week break. I was used to a traditional ordering of subject which resulted in the first semester ending with alkynes, and the second semester starting with oxidation and reduction reagents. With Karty, I planned to start my second semester with a review of Chapter 7, “An Overview of the Most Common Elementary Steps.” As Nathan Duncan wrote about in his post “An Easy Transition into the Second Semester,” Chapter 7 is a great way to refresh students’ memories and set the stage for the new material, since it allows us to revisit the heart of the text and the course. But refresh student’s memories from where into what?

Last year, I ended first semester with Chapter 10, “Nucleophilic Substitution and Elimination Reactions 2,” so that I could keep Chapters 11 and 12 (“Electrophilic Addition to Nonpolar π Bonds 1 and 2”) together. This gave me extra time to work through problems in the first semester, which is always good, but left me seriously short on time in the second semester to cover all the material I wanted to cover. I suspect that I was too worried about breaking up topics, not realizing how much a difference Chapter 7 made in their understanding. Indeed, students seemed to remember a great deal more from the previous semester than was typical for my class, and we were able to hit the ground running in January. In addition, and like Anne Wilson in “The Right Time for Synthesis,” I found that waiting until February to cover Chapter 13, “Organic Synthesis 1 Beginning Concepts,” too long to introduce the writing of reactions and retrosynthetic analysis.

So this year, I set the pace for the first semester to what I thought was practical, which meant I ended with Chapter 11. I broke up my topics and didn’t worry about the split. I trusted that the strong foundation students built in Chapter 7 would make picking up the topic reasonable if not easy. I also integrated many Chapter 13 topics throughout the first semester when appropriate. Topics such as “writing the reactions of an organic synthesis” and “cataloging reactions” might not have been explicitly taught in the text before Chapter 13, but they are so fundamental to how we talk about organic chemistry it is easy and natural to pull them in as occasional asides. I did not officially cover Chapter 13 in the first semester, but by December I found that much of the material had been introduced as part of explaining example problems or working through homework questions.

I started the second semester as I had planned with a review of Chapter 7, and then went straight into Chapter 13, treating it almost as a review as well. I kept reminding students that they knew much of this material, that we were simply discussing it all in one chapter to help remind us of problem solving process and the methodology of reaction expression. This worked extremely well. Going through the basic mechanistic steps in Chapter 7 refreshed their memories and built up their confidence (they too were worried about what they might have forgotten over break).  And while Chapter 13 was a “new” chapter, it also felt like review and reinforcement, further building their confidence and comfort level.

Another benefit to starting with Chapter 13 was that it helped break down a barrier to understanding that I’d never considered before this January. I did not realize how much of my start of the semester difficulties came from students simply reverting back to their fear of complex-looking chemical syntheses. By December, they would be comfortable with line drawings and reagents and multiple modes of expression of a chemical reaction. But come January, they would again be intimidated by all that chalk on the board. Last year, using Joel’s text, the first time I explicitly discussed these ideas was in Chapter 13, which was not the right place for my class. Before Joel’s text, I taught those concepts early in the fall but did not review them in January, leading to many of my students struggling in January and February. Simply taking the time to remind them of what they already knew, integrating Chapter 13 early on, and then teaching it as a review in January after a Chapter 7 review, has led to the most productive start of the semester that I have had in organic chemistry.

-Michelle Boucher, Utica College

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