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Mellon Lecture: Empowering Students to Learn Organic Chemistry

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Kevin Shea

on 4 April 2013

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Transcript of Mellon Lecture: Empowering Students to Learn Organic Chemistry

My Background Public High School in Connecticut - 1991

Worcester Polytechnic Institute (Worcester, MA) - 1995

Massachusetts Institute of Technology (Cambridge, MA) - 2000 How do you think I was taught? How do you think I learned? What did my early classes look like at Smith? relatively traditional, received positive feedback from college, department, and students But...there were problems Tests were too long
Limited variety of assessment types
Encouraged poor study habits with course design (students "studied" organic chemistry once per week)
Little or no student preparation before class
Most students not truly engaged I needed to get the students to do what I was doing. Force students to prepare for class
Make class active
Give more time for exams Daily Problems
Group Discussions
Library Exams Continuing My Journey 2006 - Sherrerd Prize for Distinguished Teaching
2007 - Tenure and Promotion Were my students learning all they could in my classes? Key Recent Developments at Smith 2009 - Sherrerd Center for Teaching and Learning (Director since 2010)
2010 - Participant in Smith's Faculty Teaching and Learning Seminar Focus on the Learning Sciences and what we know about how people learn Guiding Theme "Less of me is more of them, for authentic, deeper learning."
Peter Fredrick, Wabash College Empowering Students to Learn Chemistry: My Journey to Improvisational Student- and Idea-Centered Teaching Kevin M. Shea
Florida State University
Mellon Lecture
April 6, 2012 Guiding Theme "Less of me is more of them, for authentic, deeper learning."
Peter Fredrick, Wabash College The Learning Sciences Perspective on the Teaching/Learning Process Learning is active
learners do lots of thing - how they think is what counts New knowledge is built on learner's existing knowledge Successful learners are metacognitive and reflective
thinking is not just about the content, it's about how to learn the content Learning is social as well as individual
discourse and collaboration Deeper conceptual understanding
skill and information in the service of understanding Job of teachers is creating good learning environments Teacher is solely responsible for all the high level thinking to bring about learning
sets objectives
designs tasks
judges student progress Students do the work
traditional schoolwork
activities Problems Students develop no ideas about strategic activity involved learning Idea Centered Teacher Centered Teachers and learners share design responsibilities
Learners' thinking leads to understanding
Effort is focused on knowledge improvement Learning Environments Solution Knowledge Building Carl Bereiter and Marlene Scardamalia learners work together as collaborators
community's goal is improving knowledge Knowledge Problems require new learning Sustained Discourse Activity-Centered Idea-Centered Effort directed at producing a satisfactory product...learning is a by-product
Hands on Effort directed at idea improvement... learning is the product
Minds on Knowledge Forum Low Tech - 3rd Grade Day 1 Getting Started - Posting Notes Works in Progress Where do we do the best job of knowledge building currently? How have I attempted to implement these ideas in my chemistry classes? Synthesis and Structural Analysis The general goal for CHM 326 is to develop an understanding of how chemists plan, run, purify, analyze, and report reactions with a focus on practical applications in the laboratory. Additionally, we will aim to understand the theory and applications of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). At the conclusion of this class, you should be prepared to continue your chemical training in a research lab. Work in teams of three to complete three common experiments
Write each experiment up as Organic Letters paper
Each teammate has assigned responsibility for each paper
Each student graded separately
Work individually or with partner for final six-week project
Project goal - repeat two- or three-step reaction sequence from the literature; one step must generate a heterocycle
Write up like previous experiments and present results during class symposium during final lab period Knowledge Forum Computer program designed to encourage idea improvement through recorded asynchronous student contributions
An amazing tool to encourage deep student learning
Makes it possible to see student thinking; can plan class accordingly
Students help each other improve their ideas Key Tool Idea-Centered
Pedagogy and
Knowledge Forum Think like a chemist
Work productively as a member of a team
Learn how to efficiently perform database and literature searches
Evaluate hazards of chemicals and techniques
Work safely with hazardous materials
Repeat experiments described in the literature
Write clear and concise scientific papers
Learn something new from books and papers
Learn how a new instrument works
Clearly present results obtained in lab Conclusions Focus on the learning environment
What do you want your students to be able to do at the end of the course?
What are your students doing?
What are your students talking about?
How are you assessing their learning?
What tools can help your student learn more? Acknowledgements Smith Teaching and Learning Seminar - Al Rudnitsky and Glenn Ellis
My students
FSU Chemistry Department Guiding Theme "Less of me is more of them, for authentic, deeper learning."
Peter Fredrick, Wabash College Knowledge Forum I'm really confused about how to synthesize the second molecule of Question 3 from the Diels-Alder Rxn. What's kinda throwing me off is the benzene ring.

Help please? H,
I'm thinking maybe we can arrange the three double bonds (as if they are not a whole system) so that one double bond is shared between the two 6-memerbed rings. See the shared double bond as if it belongs to the ring on the right-hand side and this is the bond that the DA reaction forms. So the diene reagent actually has four double bonds in it. Thanks W! That makes so much more sense.

Also - this could possibly be a way to form benzene rings? I don't think we've ever encountered a synthesis of benzene... Thanks W! Your answer was really useful, specially the part where you mentioned that the diene is actually a quadrene (I don't know if that's what you call a compound with 4 double bonds)! Thanks that really helped but I'm still a little confused on how to do the first one on number three. I have a carbonyl on a ring with one double bond but then I lose the stereochemistry (trans)...?? Hi D! For no. 1 on Q3, since the two groups derived from the diene are both pointing into the plane, it means that they'll be trans i.e. on the same side on the diene! Furthermore, we know that the endo product is formed, i.e the electron withdrawing group on the dieneophile will go on the same side as the groups pointing outside on the diene. So since the acetate group from the dieneophile is pointing inside the plane, and so are the other 2 groups on the diene, it tells us that both the groups on the diene will point outside the diene! A series of Youtube videos explaining Diels-Alder reaction.
http://www.youtube.com/watch?v=OMqul8LmHg4 That guy is priceless and really helpful thanks! That totally explained my s-trans confusion Example Knowledge Problem From Class Synthesis of a Di- and Trisubstituted Azulene Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389-391. Fabian, K. H. H.; Elwahy, A. H. M.; Hafner, K. Eur. J. Org. Chem. 2006, 791-802. Summary Align assignments with learning goals
Use inquiry-based labs
Power of virtual learning environment
Get students writing and talking about their learning Guiding Theme "Less of me is more of them, for authentic, deeper learning."
Peter Fredrick, Wabash College “reaction was carried out with 3 equiv TpBF4 and poly(4-vinylpyridine) (123 mg/mmol of TpBF4) in 1:1 CH3CN-heptane at 65 °C for 2 h” We have come to the dubious conclusion that Fraction #1 is the azulene that we want. We have looked at the NMR ad nauseum and ... it fits better than Fraction #2. We still [have] no idea about the mechanism that created the 2nd product that we see in Fraction #2. I found a paper in the Tetrahedron which gives a pretty good explaination of why azulene is blue and napthalene is white (Pages 10-12):

The paper expained this phenonmenon using the molecular orbital theory. Azulene has a smaller energy gap between its HOMO and LUMO then napthalene, and thus it needs a longer wavelength for the transition from one to the other. This wavelength happens to be in the visible spectrum (580 nm), giving it its brilliant blue coloration.

However, anthracene has the same ionization energy as azulene, yet it is not blue. This is due to the fact that azulene is a non-alternant hydrocarbon and anthrance and napthalene are alternant hydrocarbon. The HOMO and LUMOs of neutral alternant hydrocarbons occupy the same region of space, and the HOMO and LUMOs of azulene are located in very different parts of space.

I am wondering what they mean by the HOMO and LUMOs are in different or same part of space. Is this space refering to the position of the energy levels? If anyone can come up with a diagram, I think it would be really helpful. Naphthalene and azulene are isomers. Naphthalene is a white solid. Azulene is a blue solid. So...why is azulene blue? Which compound (fraction 1 or fraction 2) is our target disubstituted azulene? Explain your answer based on comparison of your predicted NMR spectrum for the target versus the actual spectrum. What is the structure of the undesired product? Can you write a mechanism to explain its formation? The pdf is a JChem ed article with really nice illustrations of what M explained. I think our desired product is in fraction one. The spectrum for fraction one shows only peaks in the aromatic region, a singlet for the methyl attached to the five-membered ring and big singlets that correspond to the two methyl groups (6H) and the t-butyl group (9H) from the silyl group.
The other spectrum is less straightforward, but I think there is another alkene involved. Somehow we ended up with more substituents than we wanted, giving us additional peaks that are not in the aromatic region. Referring to the oroginal paper by Danheiser and Becker, we read that "reactions employing allenylsilanes lacking C-3 substituents" (this is the method we used to make our disubstituted azulene, entry 7 in Table 1) "proceed in diminished yield due to the partial destruction of the annulation product initiated by the electrophilic attack of tropyllium cation at C-3 of the azulene". Knowledge Forum Assignment Student Comments Student Comments Organic I and II Applications in Chemistry Classes Organic II General Goals
• Identify likely roles of molecules in chemical reactions (e.g. nucleophile vs. electrophile).
• Identify orbital interactions in important chemical reactions.
• Use arrow-pushing mechanisms to understand reaction selectivity and outcome.
• Predict reaction outcomes based on an understanding of structure and mechanism.
• Propose multistep routes for the synthesis of organic compounds.

Besides mastering concepts and content in organic chemistry, we aim to develop the skills and habits of scientists. You will:
• Read scientific text books for comprehension.
• Organize related information and extrapolate to new cases.
• Apply subject knowledge in a broader context (see “Real World Writing”, below).
• Communicate your understanding to others in the class. 2000 Grading 2011 Grading Quiz
Problem Sets
Hour Exams
Final Exam
Total 50
700 Percent Quiz and Exams = 71% Percent Quiz and Exams = 60% Quiz
In-Class Problems
Real-World Writing
Knowledge Forum
Problem Sets
Hour Exams
Final Exam
Total 50
1000 Student Discourse Research Lab! Think about ways to replicate the research lab learning environment in your classes. Advanced Organic Lab Class What do we know about teaching well in STEM classes? James Fairweather, Michigan State Linking Evidence and Promising Practices in Science, Technology, Engineering, and Mathematics (STEM) Undergraduate Education” a status report for The National Academies National Research Council Board of Science Education “Do we need more evidence about the effectiveness of active and collaborative teaching strategies and related efforts to foster student engagement in their own learning? No. The general literature…provides clear research evidence that active and collaborative instructional strategies are more effective than traditional lecture and discussion across most if not all dimensions of student learning.” “The largest gain in learning productivity in STEM will come from convincing the large majority of STEM faculty that currently teaches by lecturing to use any form of active or collaborative instruction.” “more effort needs to be expended on strategies to promote the adoption and implementation of STEM reforms rather than on assessing the outcomes of these reforms. Additional research can be useful but the problem in STEM education lies less in not knowing what works and more in getting people to use proven techniques.” Strategies for active learning in large classes Explain why you are doing something new
Get students to prepare for class (award points for doing things that will help them learn)
Learn as many names as you can (study!)
Use clickers to get accurate, instant feedback
Work problems in class, in small groups
Think, pair, share
Project and discuss student answers
Be flexible
Warm calling
Minute papers
Visit your colleagues' classes
Talk about your teaching
Take time to reflect
Take risks (this is what we hope our students will do!) Key Point Perfect teaching does not exist; all teaching can be improved
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