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Redesign of Organic Chemistry

Laurie S. Starkey

Cal Poly Pomona, California State University

Course Name: CHM 315 Organic Chemistry

Project Abstract: The goal is to improve the D/F/W rate in the Organic Chemistry courses by increasing in-class problem-solving opportunities.

Keywords/Tags: organic chemistry, chemistry

Instructional Delivery:  In-class

Pedagogical Approaches:  Online Homework, Exam Wrapper, Clickers

Class Size: 50

Organic Chemistry is a challenging course because:

a) it is all new to the students and like nothing they are likely to have seen before - there is little to NO PRIOR KNOWLEDGE of the subject;

b) has a significant VOLUME of information with concepts that are cumulative throughout the entire year;

c) has a fast PACE requiring a high level of student motivation, effort and time commitment; and

d) demands a high level of INDEPENDENT WORK on the part of the student - working with the textbook and solutions manual, and on assigned homework sets.

Many students are unable to commit the required time needed for success and they may have had a significant lapse in time since the General Chemistry pre-requisite course.

Organic Chemistry CHM 315 syllabus (pre-redesign)
Sample syllabus from CHM 315 before implementation of redesign.

Student Characteristics 

Organic Chemistry is largely a service course so the students come from a wide variety of majors.

Advice I Gave My Students to be Successful

Tools for Success: Organic Chemistry is a challenging course which requires a lot of time and effort on behalf of the student. The following suggestions will give you your best chance to succeed:

• Come to class and be involved! I hope the iClicker Response System will help engage you and offer real-time self-assessment. If you miss class, get the notes from someone in your study group.

• Read and work through the textbook. Take notes, try problems, be an active participant.

• Work on the textbook problems (answers at the back of the book or in the Study Guide).   A minimum of 10% of each exam will be derived directly from the textbook problems.

• Start studying now. If you wait until a few days before each exam, it'll be too late. Try flashcards!

• Review your notes often, ideally before each class. Work through your notes, ask questions.

• Come to office hours. Ask questions about the lecture, your notes, the book, your exam...

Impact of Student Learning Outcomes/Objectives (SLOs) on Course Redesign

On successful completion of this course, students will be able to:

1. Draw resonance structures and understand the effect of electron delocalization on stability and reactivity of compounds and reactive intermediates.  
   
   
2. Apply the rules of organic nomenclature to interconvert between structures and names.   Understand factors that affect acidity, basicity, nucleophilicity, electrophilicity and leaving group ability.  
   
   
3. Predict the product(s) and provide a reaction mechanism for reactions of various functional groups, including haloalkanes, alkenes, alkynes, alcohols, ethers, ketones, aldehydes.  
   
   
4. Explain observed outcomes of various organic reactions (e.g., product ratios, reaction rates, stereochemistry, regiochemistry).  
   
   
5. Learn the fundamental principles of functional group interconversion and organic synthesis. Propose a reasonable synthesis for a given target molecule.  
   
   
6. Understand and appreciate how organic chemistry is important to the student’s academic major, career field, and quality of life.

Alignment of SLOs With Course Redesign

Improving the student success rate can only be achieved by addressing all of the content-related Student Learning Outcomes (SLOs 1-5). All activities in the course redesign will be related to these SLOs.

Assessments Used to Assess Students' Achievement of SLOs

Midterm exam, final exam, surveys, American Chemical Society (ACS) standardized exam in following course, CHM 316.

Accessibility, Affordability, and Diversity Considerations

Accessibility & Diversity

Course supplements will benefit all students in our diverse student body, including those with disabilities.  Any new videos will be captioned.

Affordability

• Sapling online homework system is relatively inexpensive ($30 per quarter) but to make it even more affordable they have bundled the online access with an older edition of the textbook and solutions manual for a low-cost option. The online homework is optional to accommodate students with extreme financial hardships.
• Clickers are also inexpensive. They can be used throughout a student's entire academic career at Cal Poly Pomona and then they can be sold back to the bookstore.  iClicker has instituted a user fee for registering used clickers to another student, so I have removed that requirement  Instead, I have students submit their clicker numbers to me so I can give a small amount of participation credit.

About the Instructor, Laurie S. Starkey

I earned my B.S. in Chemistry from the University of Connecticut in 1991 and my Ph.D. in Organic Chemistry from ULCA in 1996, and I have been teaching organic chemistry and organic synthesis at Cal Poly Pomona since 1996. As a faculty member, I have been immersed in Scholarship of Teaching and Learning (SoTL) research around the use of teaching with technology, including creating and assessing online pre-lab tutorials and quizzes, developing multiple-choice questions for classroom “clickers,” providing lectures for Educator.com, creating and implementing assignments for Calibrated Peer Review (CPR) and serving on the editorial board for MERLOT. In 2012, I published a textbook for senior-level undergraduate students, “Introduction to Strategies for Organic Synthesis” (Wiley) and since 2008 I have served on the GRE-Chemistry Committee of Examiners. My community involvement includes serving on the PTA and providing a variety of hands-on science demos at my children’s elementary school every year since 2009 (see videos on my YouTube channel, ChemistryConnected!).

Curriculum Vitae
My C.V. with the details of my background and interests.

Laurie Starkey's Homepage
Dr. Starkey's homepage at Cal Poly Pomona has links to course materials, etc.

O-Chem lectures on Educator.com
The entire yearlong Organic Chemistry lecture sequence is covered by Dr. Starkey at this commercial website.

Introduction to Strategies for Organic Synthesis
The stepping-stone text for students with a preliminary knowledge of organic chemistry looking to move into organic synthesis research and graduate-level coursework.

Clicker Questions
A repository for Organic Chemistry multiple-choice questions that can be used for classroom response systems (CRS, aka "clickers").

Calibrated Peer Review (CPR)
Online tool that administers peer-reviewed writing assignments.

YouTube Channel: Hands-on Science Demos
Demonstrations of science experiments developed for elementary-level students, along with videos to support teaching and learning of Organic Chemistry.

Online O-Chem Lab Tutorials
A variety of Organic Chemistry Laboratory techniques are covered, including Recrystallization, Melting Point, Extraction, Distillation and Thin-Layer Chromatography (TLC). Each fully narrated lesson presents an introduction to theory and videos of laboratory demonstrations.

Instructor Reflection

Participating in this program has far exceeded my expectations. The reassigned time is the ONLY way that significant work can be accomplished, and I also very much appreciated being reimbursed for my days at the meetings. I came away with a hundred new ideas after the summer institute and I really enjoyed the conversations I had with other faculty at each meeting. The biweekly PLC teleconferences were mostly useful although some of them could have had better time management (less introduction and surveys, more diving right in and providing information). The chemistry group did not have additional discipline-based meeting, but I think such meetings would have been helpful since these conversations with colleagues were always helpful. What are you trying? How is it going? What works and what doesn't work? The ePortfolios are a great way to capture all the excellent work that is coming out of this program! I liked the periodic deadlines that held me accountable and helped me to break down the tasks into manageable portions. My only complaints are regarding MERLOT - it is always a slow website and I always have trouble finding my project after logging in. 

I am very excited about the changes I have implemented - and continue to refine and revise with every new course I teach. I loved this experience so much that I applied for another round! In my next course redesign project (CHM 201 in 2016-17), I will be exploring group work and encouraging a growth mindset. After gathering some more data, I would like to present my findings in a Journal of Chemical Education article.

Lessons Learned & Redesign Tips

Teaching Tips

I chose Sapling Learning for my online homework system because it is textbook independent. Pulling together appropriate assignments takes a lot of time, so I didn't want to have to start from scratch every time we switch textbooks. Another advantage to Sapling is that you are assigned a "tech TA" who helps you set up your course, answers all of your questions and quickly solves any problems that come up. It is great to get feedback from your students - what do they find most helpful? most irritating? I attempted every problem that I assigned because I wanted to be sure there weren't any glitches, especially with the drawing tool. Many problems that seemed appropriate at first glance turned out to be difficult or very time-consuming to get right, so I had to drop them. Sapling lets you create your own problems so there were some that I tweaked a bit to make them better.

Course Redesign Obstacles

This was my first attempt at using an exam wrapper. I tried implementing it through Blackboard but it was difficult to do so. In order to give credit for it, I gave it as a quiz rather than as a survey, but then it required a "correct" answer for each question so it was very confusing. When I tried it in another course the following quarter, I did it as a hard-copy survey and students attached it to their midterm, with corrections, for extra credit. This was a more effective strategy and was well received by the students.

Strategies I Used to Increase Engagement

Daily use of iClickers definitely increases engagement in the classroom. Outside of the classroom, the online homework increases the time students spend with the subject matter. As reported by my students, I believe that the exam wrapper was a useful exercise in metacognition that encourages students to learn from their mistakes.

Challenges My Students Encountered

 The online homework has a bit of a learning curve, especially for the drawing tool for drawing chemical structures. This made it challenging to implement in a 10-week quarter course, but would be lessened in a semester-long course or when it is used throughout a yearlong sequence. Although Sapling has some short tutorials available, students may not take the time to view them, so I may create some tutorial videos of my own.

Student Feedback

Online Homework

Students responded favorably to the online homework. 94% reported that they would use it again if it was available in a future course, and 83% agreed that it helped them learn organic chemistry.

Implementing the Redesigned Course

Aspects of Your Redesigned Course

• I have added an online homework system (Sapling Learning). Because there is an extra cost to the students, I have made it optional. Every chapter we cover has an online problem set to supplement the textbook problems. As an incentive to utilize the online homework, I offer extra credit to be added to each midterm exam (0.5-1 points per problem set, with a maximum of 2 points total extra credit). By capping the extra credit at 2%, students who opted out of the online homework are not at a significant disadvantage.
• I added a self-reflection exercise after the first midterm. This "exam wrapper" was administered electronically via our Blackboard LMS and was worth two points extra credit for those who completed it (added to the midterm score). By introducing metacognition concepts, I hoped that the students could improve their performance for the remainder of the quarter. The purpose of the exam wrapper is to have students consider three things:
  
  • How did I prepare for this exam?
  • What kinds of mistakes did I make?
  • What will I do differently next time?

Adopted Technologies

• Classroom Response Systems (i.e., "clickers") have been used in this class since 2008.  Every class meeting begins with a clicker question (review from previous class) and additional multiple-choice questions are incorporated into each lecture, for a typical total of 4-6 clicker questions per week.  Students vote, I write the distribution of responses on the board, and then we discuss why the right answer is right and the wrong answers are wrong.  This formative assessment is valuable to keep students engaged and on-track and provides an excellent platform to explore common mistakes. 
  
• A new technology for the course redesign is an online homework system (Sapling Learning).  The students could purchase a one-quarter license for the website ($30) or a yearlong license ($75?).  To help keep costs down, I arranged with Sapling to offer a bundle of the software with an older edition of the textbook.  This bundle was available directly through Sapling or through our bookstore.  Sapling offers exceptional technical support for faculty - I was assigned a "tech TA" who put together a scaffold for my course based on the chapters I was going to cover.  My tech TA was very prompt in answering questions and was able to solve every problem I had.  I chose Sapling because it is textbook-independent.  Setting up a new course takes a significant amount of time (possible thanks to the CSU Course Redesign course release!) so it was critical for me to know that I could continue to use this site and these assignments even if we were to change textbooks in the future.  Organic Chemistry lectures are taught by several instructors and we decide on a common textbook by committee.
•  Another technology I tried was using Blackboard to administer an electronic exam wrapper assignment.  I liked it because I didn't have to handle the papers, but it had drawbacks too.  If the questionnaire was administered as a "survey" in Blackboard then it was treated anonymously and I wouldn’t be able to give extra credit. However, if it was give an a “quiz” then it required correct and incorrect answers so it was awkward to set up and there were glitches in the “grading.” I decided the following quarter to administer it as a hard-copy survey and to couple it with an opportunity to submit corrections to the problems the student got wrong. I offered 2 extra credit points for the survey and an additional 2 points for making corrections. In addition, I covered the name and photocopied each survey so I could work with the data at a later date. I am interested in looking for trends in various student populations (e.g., study habits for those who are repeating the course).  

Professional Development Activities Participation During Course Redesign

• I have made use of every opportunity available through the Course Redesign program: weeklong summer institute, Professional Learning Community (PLC) teleconferences every two weeks, daylong mid-year meeting in Long Beach. All of these have been very useful and have given me many great active-learning strategies to work with.
• In addition, I always make every effort to participate in programs on campus sponsored by the Faculty Center for Professional Development. It was a learning community organized by our FCPD that got me interested in promoting active-learning by using clickers, another PLC taught be about metacognition, and various speakers/workshops have explored how to address the affective domain in teaching and learning and how to get students to participate in class.
• I am looking forward to presenting at the upcoming CSU Teaching & Learning symposium in attending Chemical Education talks at an upcoming National American Chemical Society meeting. I regularly attend ACS meetings, but my decision to participate in the CSU symposium was a direct result of discussions at the mid-year meeting.

Additional Resources for the Redesign

• I have consulted with institutional research to determine the D/F/W rates for organic chemistry in the past so I can supplement my own historical data with department-wide statistics.
• I have worked with Sapling Learning to learn about the software, secure a low-cost textbook bundle, and to implement the online learning system in my course.
• The Cal Poly Pomona Faculty Center for Professional Development has been helpful as described above.

Organic Chemistry CHM 315 syllabus (revised)
Post-redesigned syllabus includes reference to online homework system (Sapling).

Organic Chemistry CHM 315 Exam Wrapper
Post-midterm self-reflection exercise. Administered in Blackboard LMS.

Course Redesign Impact on Teaching and Learning

The biggest change I made to this particular course was to add an online homework system. Now that I have it in place, I can continue to revise and improve upon its implementation. I have 1-2 assignments per chapter and I offer extra credit for doing the online homework and achieving a minimum grade. Traditionally, the only source of problems to work on comes from the textbook. This old-fashioned approach works well for those students who are highly motivated, but I believe it fails to be effective for the majority of students. If working on textbook problems is the primary method for succeeding in Organic Chemistry, then I have to explore any method possible to increase the number of problems the students work on. I believe that having the online homework did increase the number of students who worked on problems and, therefore, helped more students achieve the learning outcomes. The online homework was optional, since it was an additional expense ($30 for the quarter). Out of 101 students, 73 subscribed to the online system. The students in this particular quarter did as well as most of my CHM 315 students since Winter 2008 (when I started using iClickers to supplement my teaching).   An unexpected result is that I have created new clicker questions and in-class activities as a result of some interesting and/or challenging problems that I discovered in the online homework system. Rather than assign them as part of the homework, I used them as the starting point for discussions and problem-solving demonstrations.

Assessment Findings

I have been teaching CHM 315 since Winter 1997. Over the course of the past twenty years, I have improved as an instructor and I have implemented numerous effective resources. As a result, the performance of my students has steadily improved, with a gradual but steady decline in my D/F/W rate. No two student populations are the same, and none of the data presented below have been corrected for student GPA's or pre-requisite course grades. Interventions and improvements include:

• iClicker (classroom response system) used in CHM 315, since Winter 2008
• skeleton notes for every chapter to guide classroom discussion, since Winter 2010
• all of my Organic Chemistry lectures are available online at Educator.com (free of charge for my students), since Winter 2011
• online homework system (Sapling), since Fall 2015 (CSU Course Redesign)
• exam "wrapper" metacognition exam-reflection exercise since Fall 2015 (CSU Course Redesign)

Student Feedback

 An anonymous survey was administered at the end of CHM 315, using Survey Monkey. Out of 101 students, 45 responded. For the new materials used in this course for the Course Redesign, students described them as useful but not among the most useful resources in my course, as shown below. Students found the online homework to be about as useful as the textbook, with all students finding it useful but only 47% describing it as "extremely useful." By comparison, 89% of the respondents reported that my lecture handouts were "extremely useful." 93% students found the Exam I reflection exercise to be useful but only 30% described it as "extremely useful."

Student Feedback

Exam Wrapper

Students seemed to recognize and appreciate the value in reflecting on their midterm performance. The majority (73%) spent more time than usual reviewing their mistakes and 59% reported that it is at least somewhat likely that participating in the post-test reflection survey improved their grade on their second midterm and/or their final exam.