CHEM 358: Organometallic Chemistry

Structure, Bonding, and Reactivity of Organotransition Metal Complexes (Winter 2021)
Please see course Moodle page for detailed info

General Course Info

Online or in CMC 306, Period 4a (MW 1:00-2:10 PM; F 1:50-2:50 PM)

We will use class meeting time for a variety of purposes, including lecture, group problem solving, primary literature discussion, and presentations.

Office Hours (see Moodle page for Zoom link):

  • Tu 1:30-2:30 PM
  • Th 10:00-11:00 AM

In this course, we will take a small-molecule-activation approach to the field of organometallic chemistry. Using simple yet powerful techniques such as electron counting and isoelectronic/isolobal arguments, we will build a foundation for explaining and predicting the structure, bonding, and reactivity of transition-metal complexes. I think that this is a fascinating and important area of chemistry, and I hope that by the end of the course (if not before) you will share my excitement!

Prereqs: A basic knowledge of general (CHEM 123) and organic chemistry (CHEM 233/234) is assumed. Beyond that, I expect that there will be a range of backgrounds. We’re in this together! Be on the lookout for connections to other classes or research experiences that you can use to strengthen your knowledge and help others learn. Be sure to keep me in the loop and let me know if you think my assumptions about background knowledge or the pace of the course are not appropriate.

This is an upper-level course with a strong emphasis on the primary literature, covering much of the content of a graduate course in organometallic chemistry, and is great preparation for Chemistry Comps!

Primary Learning Goals:

  • Identify key patterns in structure, bonding, and reactivity for organic and organometallic complexes
  • Apply these patterns to propose mechanisms for new reactions (including catalytic reactions) and understand/contextualize findings from the literature
  • Evaluate and critically analyze the primary organometallic literature, including devising experiments to test mechanistic hypotheses
  • Assess and articulate the utility of transition metals in organic synthesis

Ancillary skills:

  • Peer teaching and learning through group work
  • Framing good questions and critically reading the primary literature
  • Using databases (SciFinder, Web of Science, CSD) to search the primary literature
  • Constructing an overarching narrative from multiple primary sources

Here are some important details about the structure of this online course:

  • Moodle will serve as the centralized course space – All information about the course will be posted on Moodle and I will use Moodle messaging for announcement. All course topics will be organized in appropriate sections on Moodle, and you will use Moodle to turn in completed assignments. I am hoping we can use Slack (‘Organometallica’ channel) as an informal channel for asking questions of each other, sharing insights and cool papers we stumble across, and plumbing the depths of Organometallica!
  • Lessons will be posted as short (~20 minute) videos – I will record videos that will be linked from Moodle and Panopto addressing a variety of topics during the term. These will stand in for the “lecture portion” of class time, since I don’t want to waste our synchronous time lecturing at you.
  • Additional resources – A variety of additional resources (practice problems, literature readings, my notes, useful websites and notes from others) will be posted on Moodle. You also may find it helpful to check out the following texts to provide addition perspective on the material we will cover (all available from the library):
    • Miessler & Spessard, Organometallic chemistry (3rd)
    • Crabtree, The organometallic chemistry of the transition metals (available electronically)
    • Hartwig, Organotransition metal chemistry: from bonding to catalysis
  • Synchronous activities
    • Class meetings: We will have Zoom class meetings every week on Wednesdays and Fridays during the scheduled time. Mondays will frequently be used for open Q&A (either in-person or hybrid) or as an opportunity for breakout meetings. I will update you on the meeting plan in advance of each week.
    • Office hours: I will host open office hours on Tuesday afternoons (1–2 PM) and schedulable (in 20-min blocks) office hours on Thursday mornings (10–11 AM). I am happy to schedule additional times as needed, just let me know what works for you.
  • Organometallic Weekly Update – To facilitate communication and minimize the number of emails you receive, I will put together a newsletter each week that will preview new material for the week, outline assignments that are due and videos that will be posted, and give info about all synchronous meetings. I will also provide a suggested weekly workflow since it can be difficult to keep up with everything in a primarily online setting.

Assigned Work and Grading

Homework assignments are a great chance for you to practice what you have learned with some difficult problems. They will begin more or less weekly but taper off as we get more into primary literature discussions and critical review paper writing later in the term. Assignments are due via Moodle (as a pdf) at 5 PM on the day indicated, but I will give an “automatic grace period” of 15 hours (until 8 AM the next day, when I download the batch of assignments).

Collaboration with Classmates: Collaboration with classmates is strongly encouraged, but it is important for you to be able to recognize which parts of the material you understand well and which need more work. Therefore, you should acknowledge any help or insights you receive from others (including me), on your submitted work.

Late Homework Policy: In general, homework assignments that are turned in late will not receive any credit but will be graded for your benefit. However, you will be given 2 “passes”, which will allow you to turn in an assignment by 5:00 PM two days following the assignment due date. These assignments will be graded for full credit.

The course participation portion of the final grade reflects your contributions to the collaborative learning environment that is central to CHEM 358. The contributions can take a variety of forms:

  • Engagement in group problem solving in class
  • Contributing to collaboratively reading the primary literature by annotating in and participating in forum discussions
  • Contributing to literature discussions (coming prepared and engaging with discussion leaders)
  • Work with a group leading a primary literature discussion
  • Supporting others’ learning (e.g., posing good questions, making insightful comments and recognizing connections, supporting a constructive learning environment by amplifying and building on others’ insights, making a productive mistake that helps everyone’s understanding)
    • You are strongly encouraged to recognize others’ contributions to your learning as part of your weekly check-ins

One-third of the course participation grade comes from class-led primary literature discussions (your work as a leader and participant); the remainder comes from other venues (Workshop Wednesdays, discussions with visiting professors, collaborative annotations in, etc.).

In terms of contributions to group learning, quality is more important than quantity. I also recognize that everyone will be naturally drawn to contribute in certain ways more than others, and that is okay. ‘A’-level work reflects consistent engagement through the term in various venues and a sustained commitment to being prepared for class activities and willingness to fill a variety of roles as needed.

There will be two midterm exams, contributing 20% to your final grade, and a final exam accounting for 20% of your final grade.

Midterm Exam #1: due Monday, February 1st at 5:00 PM

Midterm Exam #2: due Monday, March 1st at 5:00 PM

Final Exam: March 13–15 (details to be provided)

The major writing assignment for this course is a short (4 to 5 pages journal-style) critical review paper addressing a topic of current interest in organometallic catalysis or small-molecule activation. You will receive a detailed handout about this assignment during the first week of class, and we will discuss my expectations for the review in more depth during the second week of class.

You will benefit from starting this assignment early, and I am providing several intermediate deadlines to encourage you to do so. Timely and thorough completion of these intermediate assignments will contribute to your final grade on the writing assignment. The Late Homework Policy (see above) applies to the intermediate assignments, and you may use your “passes” on these.

Guiding Paper Summary & Next Steps: Wednesday, January 27 (5:00 PM)

Short Summaries (3 paper) & Outline: Wednesday, February 10 (5:00 PM)

Draft Due for Peer Review: Wednesday, February 24 (5:00 PM)

Peer Reviews Due: Wednesday, March 3 (5:00 PM)

Final Draft Due: Wednesday, March 10 (5:00 PM)

  • Homework: 15%
  • Course Participation: 15%
  • Midterm Exams: 25%
  • Final Exam: 20%
  • Critical Review Paper: 25%

Grade cutoffs: A 93%, A- 90%, B+ 87%, B 83%, B- 80%, C+ 77%, C 73%, C- 70%, D+ 67%, D 60%

Academic Policies

Intellectual integrity is paramount in the learning process and is central to the process of self-discovery that is at the core of a liberal-arts education. I expect that, to the extent that other resources are not referenced, all of your graded assignments represent your own work (see the Homework section for more detailed instructions on homework). You can find some good general resources about academic honesty on the Carleton site: If you are unsure about any issue related to academic integrity, please ask me.

I committed to offering this class in a way that serves all students equitably. If you need accommodations based on a documented learning disability or other special need, please make me aware of this at the beginning of the term and/or contact the Carleton College disability services office to ensure that we can take appropriate measures to facilitate your learning experience.