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

2. 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

3. 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.

4. 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

5. 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

6. 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.

7. 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 ...”

8. Cognitive Psychology and the Spiral Approach
p 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 …”

9. 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

10. 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

11. “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%

12. “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

13. “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

14. “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

15. “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

16. “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%

17. 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.

18. 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

19. ) ) ) ) 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. ) )

20. 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.

21. 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.

22. 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:
Questions??

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