a spiral organic chemistry sequence, 12 years after ......intro. to all the major functional groups,...

A spiral organic chemistry

sequence, 12 years after

implementation

Doug Schirch

BCCE July 2018

Outline

1. Why I switched

2. Course organization

3. Cognitive psychology and the spiral

approach

4. Results of ACS final exams before and

after switch

5. Student opinions

6. 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

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

Content Organization

Chapters from Carey, 9e

Chap. Fall Sp. 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

0

10

20

30

40

50

60

'05 '06 '07 '08 '10 '11 '12 '13 '14 '15 '16 '18

# Correct on

2002 ACS Org Chem

(70 Q.)

Year

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% 0

Disagree 0 0

Neither agree nor disagree

0 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%


2 12% 3 10%

Agree 1 6% 2 7%

Strongly Agree 0 0

• “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%


2 12% 7 23%

Agree 1 6% 0

Strongly Agree 0 0

• “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%


6 35%

Agree 3 18%

Strongly Agree 0

• “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


Disagree 11 37%


7 23%

Agree 7 23%

Strongly Agree 0

• “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


Disagree 1 3%


1 3%

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





Fall grade Spring: ave. change % # ↑ # ↓A -0.5 23 36

A- 0.5 11 8

B+ 1.3 10 6

B -1.7 9 11

B- -0.8 3 3

C+ -3.5 3 5

C -7.6 1 3

C- -39.4 0 2

D/D+ -19.8 0 2

Other Observations





)

)Now blocked from 2nd

sem.

)

)

Half went up 1-2 grade steps.

Fall grade Spring: ave. change % # ↑ # ↓A -0.5 23 36

A- 0.5 11 8

B+ 1.3 10 6

B -1.7 9 11

B- -0.8 3 3

C+ -3.5 3 5

C -7.6 1 3

C- -39.4 0 2

D/D+ -19.8 0 2

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

• Spiral approach

– 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: [email protected]

Questions??

mailto:[email protected]

Recognition

• Dan Berger, Bluffton University

• Michael Garoutte, Missouri Southern State

University

• Goshen College Faculty Development Funds

a spiral organic chemistry sequence, 12 years after ......intro. to all the major functional groups,...

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