Students are Doin’ it for Themselves

As several contributors to this blog have pointed out, Joel Karty’s text introduces biochemistry topics early in the course through supplementary sections at the end of most chapters titled, “The Organic Chemistry of Biomolecules.” Many instructors have lauded this early inclusion of biomolecular topics as a motivator for biology majors and pre-professional students; one that facilitates understanding of subsequent and current coursework in biochemistry and biology. In addition, the modular nature of these sections provides significant flexibility for instructors, allowing us to decide what to teach and when to teach it.

During my year-long organic course for chemistry majors, I skipped over the biomolecule sections in the first quarter with plans to return with a single biochemistry unit in the spring quarter. Needless to say, it didn’t quite work out that way. The active learning emphasis of the course (see my previous post titled  POGIL and Mechanisms are Natural Allies) slowed our progress, leaving us without adequate time for a biochemistry unit at the end. Instead, I decided to introduce beginning biochemistry topics through take home portions of hour exams. The biomolecular topics addressed in these assignments include chirality in biochemistry, pH and amino acids, and major classes of biomolecules. Since the reference sections of the Karty text were from early in the course, student’s anxiety is reduced toward the self-directed learning experience. Ultimately, with the strong foundation afforded by the course and the Karty text, the students had developed skills necessary to handle this material on their own.

By the time we approached later biochemical topics, such as aromaticity and DNA (14.12), and mutarotation of monosaccharides (18.14), it was apparent that there would not be enough time for a large biochemistry unit at the end of the course. Thus, these topics were fit into their respective chapters, or soon thereafter. For example, heterocyclic aromaticity can be a rather obscure topic without the application of DNA base pairing. Likewise, hemi-acetal formation seems rather pointless without discussing monosaccharide cyclization, and biomolecular polymers fit naturally in a discussion of polymers of all types (Ch26).

By incorporating biomolecular topics in multiple ways and formats, my students apply organic structure and principles in biomolecular systems, in a manner seamlessly supported by the Karty text. Skipping early biomolecule sections allows students to focus on the organic chemistry fundamentals at the beginning of the course. Later, self-directed learning provides an introduction to structure and acidity topics in biomolecules, while grabbing the interest of the students with a biochemistry concentration. The introductory nature of the early topics also provide both a review of fundamentals or organic chemistry, and a confidence boost for students. Further along in the course, biochemistry-oriented topics fit well with the organic content surrounding them, providing  natural pathways linking organic chemistry and biomolecular subject matter, and therefore leaving my students with a more substantial understanding.

-Kimberley Cousins, California State University, San Bernardino

From Cover to Cover

As of a couple hours ago, I have not only completed my first full year as a lecturer at Northern Arizona University, but I have also completed my first full cycle of Karty’s text; from Fall 2015 to Spring 2016, from Organic Chemistry I to Organic Chemistry II, from front-cover to back-cover of Organic Chemistry: Principles and Mechanisms. I have been fortunate in this time to see my Organic Chemistry I students graduate on to my Organic Chemistry II course, and further fortunate for the opportunity to participate in a major part of their education. But for all the hard work we all put into the class, in the end, a course cannot be taught without structure or a story. Using Karty’s text as the structure, I was able to tell the story I had prepared nearly nine months ago.

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Are Mechanisms Just for Chemistry Majors?

Like many chemists, I am not much help to the biology, biomedical, and medical students that come to my office with queries ranging from anatomy to physiology. Though a prerequisite for my degree, biology was never a true passion of mine. Likewise, many biology majors despise chemistry. In fact, a number of the biology majors in my organic chemistry courses dislike chemistry so much that they fear it. Of those students, most find organic chemistry, in particular, to be their least favorite course in college.

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Starting the Semester with My Biology Students in Mind

Like so many other organic courses, at my school approximately two-thirds of organic students are biology majors. Of these, most have some sort of pre-health professional aspiration. Because of this audience alongside my chemistry and biochemistry majors, I come to my organic classroom (as I know many of you do!) with two sets of course goals in mind; there is the amazing world of organic synthesis and mechanistic theory that I want to teach, and there is the looming MCATs, PCATs, and other standardized exams that many of the students have in their futures. The students need a solid foundation in organic chemistry as preparation for biochemistry, inorganic chemistry, and beyond, but I also want them to appreciate organic synthesis as beautiful and elegant and not simply a stepping stone to another course. The challenge for me has always been how to balance how much I should cater to my biology students, finding every possible biochemical hook to interest them and tying everything to a standardized exam question, versus pushing forward a chemical worldview where they learn to appreciate a molecular approach and to think like an organic chemist.

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Biomolecules Hidden in Plain Sight

When I consider adopting a new textbook for a course, I have one main concern: my audience. I teach a wide variety of students; the chemistry major who began doing research his freshman year on his path toward graduate school, the psychology major who is concerned about his GPA and preparation for the MCAT, the art major who finds chemistry interesting enough to pursue a minor, and the biology major who is just hoping to pass to fulfill requirements for graduation. Balancing the needs and interests of such a varied audience is always a challenge, but careful choices in the organization and framing of the course can help.

Traditional textbooks have an organization based on functional groups, but my experience is that true mastery of a topic comes with an understanding of underlying concepts, enabling application to new situations. There is only so much a person can memorize, but building a mental model by making contextual connections using a strong framework leads to greater success and retention. Needless to say, Joel’s textbook and its mechanistic organization jumped out as an exciting change of pace with its emphasis on understanding the electron movement. But a quick glance through the table of contents begged the question, where is the chapter on biomolecules, the traditional bridge to the subsequent biochemistry course?

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Reasoning By Analogy

For twelve years I’ve taught organic chemistry to a mixture of chemistry and biology students. I always begin Organic I by asking my students this same question: Why are you taking this class? Some students respond that the curriculum plan for their major or career requires the organic chemistry course sequence. For other students, organic chemistry is a hoop through which they must jump in order to prove to admissions boards that they have the ability to succeed in their chosen graduate or professional programs. Many students just shrug their shoulders—they, in fact, honestly don’t know the answer. In response, I tell my students that the universe is filled with countless molecules that can undergo innumerable reactions. I tell them that, even so, this overwhelming multitude can be organized by a rational set of structural and reactivity principles. And I tell them that this organizational framework has power, both descriptive and predictive. I tell them that, no matter the reason they are taking organic chemistry, they are here, in part, to learn to reason by analogy, to learn to recognize, to explain, and to extend patterns.

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The Three M’s: Motivating, Modernizing, and MCAT

At most colleges and universities, students enrolled in organic chemistry come from a variety of majors and pre-professional programs. At St. Kate’s, the organic sections are a 20/20/40 split of chemistry, food & nutrition science, and biology majors. Twenty percent of our students are enrolled in organic in order to fulfill prerequisites for a variety of pre-professional programs and to prepare for the MCAT or PCAT. These diverse demographics require me to purposefully prepare a variety of examples that connect a student’s career interests to organic chemistry concepts. In my experience, the examples that students typically find the most engaging have biology roots or are pulled from the most recent chemistry and technology advances.

In the past, I have not had time to teach the biochemistry chapters that often appear at the end of organic textbooks. This changed, however, when I started using Karty’s book, because his text includes “Organic Chemistry of Biomolecules” sections that appear at the end of chapters. Continue reading