A spiral organic chemistry sequence, 12 years after implementation Doug Schirch BCCE July 2018

Outline Why I switched Course organization Cognitive psychology and the spiral approach Results of ACS final exams before and after switch Student opinions Observations and other course elements

Why I switched (Thank you Dan Berger) 1-semester students (Biology and Environmental Science majors) Miss many functional groups common in nature (carboxylic acids, amides, esters, amines, etc.) Forced to learn less relevant material Can’t offer separate courses Appeal of More incremental difficulty during year. Forcing students to review in 2nd semester.

Content Organization 1st Semester 2nd Semester Review of bonding theories, EN, etc. Const. and geometric isomers, conformers, intro to chirality Intro. to all the major functional groups, their nomenclature, and properties Fundamental reactions for each functional group Major mechanisms Multi-step synthesis problems Lab: Standard purification techniques, TLC, melting points, a synthesis, GC-MS

Content Organization 1st Semester 2nd Semester Review of bonding theories, EN, etc. Const. and geometric isomers, conformers, intro to chirality More depth on nucleophilic substitution and chirality Intro. to all the major functional groups, their nomenclature, and properties Spectroscopy Fundamental reactions for each functional group Additional reactions Major mechanisms Additional mechanisms Multi-step synthesis problems Longer multi-step synthesis problems Lab: Standard purification techniques, TLC, melting points, a synthesis, GC-MS Lab: Syntheses, literature project, qualitative analysis using MS, FT-NMR, FT-IR

Chapters from Carey, 9e Chap. Fall Sp. 1. Structure/properties √ 12. Aromatic subst. 2. Alkanes 13. Spectroscopy 3. Conformations 14. Organometallic cmpds 4. Alcohols, alkyl halides 15. Alcohols, thiols 5. Alkenes: structure & prep. 16. Ethers, epoxides 6. Alkenes: add’n rxns 17. Aldehydes, Ketones 7. Chirality 18. Carboxylic acids 8. Nucleophilic subst. (√) 19. CA deriv.; Nu acyl subst. 9. Alkynes 20. Enols, enolates 10. Conjugation; allylic syst. 21. Amines 11. Arenes, aromaticity 22. Phenols POGIL worksheets are used in some chapters. Ch. 3 is mostly a 3-hr. POGIL lab.

Cognitive Psychology and the Spiral Approach What we’ve learned from cognitive psychology about techniques for successful learning. p.47. Spaced Practice. “The increased effort required to retrieve the learning after a little forgetting has the effect of retriggering consolidation.” p. 49. Interleaved Practice (of two or more subjects). “… research shows unequivocally that mastery and long-term retention are much better if you interleave practice ...”

Cognitive Psychology and the Spiral Approach p. 78. Easier Isn’t Better. “… the easier knowledge or a skill is for you to retrieve, the less your retrieval practice will benefit your retention of it. Conversely, the more effort you have to expend to retrieve knowledge or skill, the more the practice of retrieval will entrench it.” p. 81. “In other words, the more you’ve forgotten about a topic, the more effective relearning will be in shaping your permanent knowledge.” “This works to “bolster the cues and retrieval routes for recalling it later, and weaken competing routes.” p.87. Unsuccessful attempts to solve a problem encourage deep processing of the answer when it is later supplied, creating fertile ground for its encoding …”

Scores on ACS Final Exam - 2nd Semester 2-tailed student’s t-test: only 3% probability 2 populations are the same. Standard sequence Spiral sequence

Survey of Student Perceptions 2010: Survey sent to all previous students from the 3 years a spiral sequence used. Of 31 one-semester students, 17 (55%) responded Of 49 two-semester students, 30 (61%) responded

“I think it was good to have the first semester of the course be a general survey of organic chemistry that covers the fundamental topics relevant to biology.” 1-semester students 2-semester students Strongly Disagree 1 6% Disagree Neither agree nor disagree 2 7% Agree 6 35% 15 50% Strongly Agree 10 59% 13 43%

“I found it confusing to be skipping some chapters or sections in the textbook.” 1-semester students 2-semester students Strongly Disagree 3 18% 7 23% Disagree 11 65% 18 60% Neither agree nor disagree 2 12% 10% Agree 1 6% 7% Strongly Agree

“I think it would be better to follow the standard sequence, going through the first half of the text in the first semester and the second half of the text in the second semester..” 1-semester students 2-semester students Strongly Disagree 3 18% 8 27% Disagree 11 65% 15 50% Neither agree nor disagree 2 12% 7 23% Agree 1 6% Strongly Agree

“For the content we covered in the first semester, I think I would have learned better with a smaller textbook designed for a 1-semester introduction to organic chemistry course, instead of the larger 2-semester text that we used parts of.” 1-semester students Strongly Disagree 1 6% Disagree 7 41% Neither agree nor disagree 6 35% Agree 3 18% Strongly Agree

“Instead of the large 2-semester text that we used for both semesters, I think I would have learned better with a smaller textbook designed for a 1-semester introduction to organic chemistry course in the first semester, and then only using the larger 2-semester text for the second semester.” 2-semester students Strongly Disagree 5 17% Disagree 11 37% Neither agree nor disagree 7 23% Agree Strongly Agree

“Seeing some material twice during the year (at an introductory level in the first semester and in more depth during the second semester) helped me learn the material better by the end of the course.” 2-semester students Strongly Disagree 0% Disagree 1 3% Neither agree nor disagree Agree 12 40% Strongly Agree 16 53%

Other Observations Students often do better in the 2nd semester, even though the material is more difficult. But those with too many deficiencies from the 1st semester crash and burn in the 2nd semester.

Other Observations Students often do better in the 2nd semester, even though the material is more difficult. But those with too many deficiencies from the 1st semester crash and burn in the 2nd semester. Fall grade Spring: ave. change % # ↑ # ↓ A -0.5 23 36 A- 0.5 11 8 B+ 1.3 10 6 B -1.7 9 B- -0.8 3 C+ -3.5 5 C -7.6 1 C- -39.4 2 D/D+ -19.8

) ) ) ) Other Observations Students often do better in the 2nd semester, even though the material is more difficult. But those with too many deficiencies from the 1st semester crash and burn in the 2nd semester. Fall grade Spring: ave. change % # ↑ # ↓ A -0.5 23 36 A- 0.5 11 8 B+ 1.3 10 6 B -1.7 9 B- -0.8 3 C+ -3.5 5 C -7.6 1 C- -39.4 2 D/D+ -19.8 ) Half went up 1-2 grade steps. ) Now blocked from 2nd sem. ) )

Other Observations Problem: 1st semester: Need for additional homework problems. Benefit: chapters finished quicker, meaning homework due more frequently. Assistance for reviewing content on 2nd visit to a chapter: Reaction cards required in 1st semester. Moodle quizzes the night before a POGIL packet.

Other Helpful Tools Weekly 10-min. quizzes (17-20% of grade). Incentive to be in study groups (3 hrs/wk). Discovery labs that anticipate class content (e.g. carbocation rearrangements) 3 practice exams before each exam. Exam wrappers.

Summary Questions?? Spiral approach For more info: dougms@goshen.edu A much better experience for 1-semester students Supported by cognitive psychology for 2-semester students. 2-semester students show increased learning and prefer the spiral approach. The most significant problems (lack of specific text, skipping sections, and transfer students) are not deal-breakers. For more info: dougms@goshen.edu Questions??

Recognition Dan Berger, Bluffton University Michael Garoutte, Missouri Southern State University Goshen College Faculty Development Funds