I cannot write my final exam… until the class finishes the book

Brian P. CoppolaArthur F. Thurnau Professor of ChemistryAssociate Chair for Curriculum and Faculty AffairsFaculty Associate, Center for Research on Learning & Teaching

Year 1: General Principles (+ opt lab) Structure/React 1 (+ analyt) Structure/React 2 (+ lab)

Year 2: Intro Phys (lec) & Analyt (leclab) Intro Inorganic (Bio/Materials) Combined Org/Inorg lab

Year 3: Biochemistry 1/2 (& genetics) (bio)Physical & Analytical (+ lab choice)

Intermediate Inorganic & electivesYear 4: electives (incl. writing/speaking)

[grad classes & research]

1500 enter here placement 65% engin 95% 1st-yr

Yield : 50-90 majors (1:2 Chem:Biochem)

1989 - date

1100 enter here placement; AP, 55% 1st-yr

Context

Technology-Assisted Instruction

Instructional targets…

1DisciplinaryKnowledge

Molecular structural evidence comes from experimental data.

Instructional targets…

1SubjectMatterMastery

DisciplinaryKnowledge

C5H10

A: C5H12O m/e 88, 73, 45

B: C5H12O m/e 88, 59

1) B2H6

2) H2O2

Molecular structural evidence comes from experimental data.

Instructional targets…

1SubjectMatterMastery

DisciplinaryKnowledge

Transferable Skills

C5H10

A: C5H12O m/e 88, 73, 45

B: C5H12O m/e 88, 59

1) B2H6

2) H2O2

Molecular structural evidence comes from experimental data.

Fact/text versus inference from fact/text.Suspending judgment.Triangulation.

Alignment…

1Instructional Goals

Molecular structural evidence comes from experimental data.

Alignment…

1Instructional Goals

Pedagogical Method

Molecular structural evidence comes from experimental data.

Pedagogical organization of the topic.Self-directed/peer-led team instruction.Situated learning: literature & laboratory.

Alignment…

1Instructional Goals

Pedagogical Method

Assessment Tasks(for grades)

Molecular structural evidence comes from experimental data.

Pedagogical organization of the topic.Self-directed/peer-led team instruction.Situated learning: literature & laboratory.

Case study problems.Authentic laboratory tasks (library->lab).Student-generated instructional material.

PCK: Pedagogical content knowledge

1Assessment Tasks(for grades)

Case study problems.Authentic laboratory tasks (library->lab).Student-generated instructional material.

IV. (20 points; J. Org. Chem. 2002, 67, 988)

HO

O

NOCH3

CH3NH

O

The mass spectrum of compound C shows the following peaks:m/z = 296 (M+), 278, 236, 163, 91

Compound C

(a) Provide an appropriate molecular ion for Compound C that can be used to explain the formation of the fragment at m/z = 278 amu. Provide the complete, step-wise mechanism for this fragmentation and give the balanced equation.

28 proposals

7 proposals

4 proposals

goto: www.umich.edu/~chemh215

2The value of teaching in learning

“Preparation to teach the contents of a text versus to understand it personally may influence the mental representations that are created from text.”

Coleman, E.B.; Brown, A.L.; Rivkin, I.D. “The Effect of Instructional Explanations on Learning from Scientific Texts” Journal of the Learning Sciences 1997, 6(4), 347-365.

Coleman, E. B. "Using Explanatory Knowledge During Collaborative Problem Solving in Science." The Journal of the Learning Sciences 1998, 7(3&4), 387-427.

2The value of teaching in learning

If you are mentally aware of the future need to explain a concept to someone else, then you will learn the concept better than if you are only learning it for yourself.

Coleman, E.B.; Brown, A.L.; Rivkin, I.D. “The Effect of Instructional Explanations on Learning from Scientific Texts” Journal of the Learning Sciences 1997, 6(4), 347-365.

Coleman, E. B. "Using Explanatory Knowledge During Collaborative Problem Solving in Science." The Journal of the Learning Sciences 1998, 7(3&4), 387-427.

2Structured Study Groups

• 2-hr Supplemental session, formal curriculum• led by junior & senior undergraduates• structured peer review• new lessons, O/S/U evaluation• library/journal searches, FMO, spectroscopy, bio-

organic, ethics, writing, meet the author, physical organic, computational chemistry

• second-semester:

the HTML project

student-design laboratory projects

student-generated ethics case

2Structured Study Groups

1st Assignment

• each student selects journal, year

• find a C10-13HxX2-3 molecule, cite it

• create 5 new, rational molecules• rank by 2 of: mp, bp, solubility, DM• write paragraphs to explain ranking• bring two copies to the meeting

– student-generated work– studio environment– conversations begin (not end) with answers

SSG Assessment ChecklistAssignment No. 1: Constructing Molecules & Predicitng Properties

Whose Paper are you Reviewing?______________________________________Reviewer One's Name?______________________________________Reviewer Two's Name?______________________________________

Rev. 1I. The Citation.

A. Is there a copy of the Journal article attached? Yes NoB. Was a citation created for the assignment? Yes NoC. If a citation is present, is it done correctly? Yes No

II. The Selected Molecule.A. Does molecule selected meet the C10-13Hx(heteroatom)2-3 criterion? Yes NoB. Has the molecular formula been determined correctly? Yes No

III. The Created Examples.The First OneA. Does the example have the same molecular formula as the original? Yes NoB. Is the structure of the example valid? Yes No

IV. The Physical Properties.The First OneA. Is there a first physical property selected for the examples? Yes NoB. Are all of the examples ranked according to this property? Yes NoC. Are the examples ranked appropriately? Yes NoD. Is the justification for the ranking rational? Yes NoE. Is the english grammar fair, good, very good, or excellent? F G V EF. Evaluate the punctuation & other technicals: F G V E

Assignment No. 2 Quiz 1997 Chemistry 210 SSG Section 001

Name _______________________________ quiz created by: Pat Smythe

In a recent journal article, Schwink and Knochel reported the following transformation involving an interesting molecule where an iron atom is sandwiched between two rings (Schwink, L.; Knochel, P. Tetrahedron Lett. 1996, 37, 25-28.). Provide a description of the bonding changes taking place in this reaction.

Fe

C

O

C

O

C

O

CH3

C

O

CH3

H

H Fe

C

S

C

S

C

O

CH3

C

O

CH3

H

H

SC

O

CH3K

2

OC

O

CH3K

+ 2

2nd Assignment: find a substitution

Name _______________________Page 2

II. (40 points)

H

O

H

H3C

H

HH3C H OH

O

O

O

H

OH

HO

H

H

OH

H CH3

A. Amphidindolide H3 is a newcyctotoxic compound isolatedfrom the marinedinoflagellateAmphidinium .(JOC,2002, 67, 6585).

(a) Circle the centers towhich R or S can beassigned, and then label them as one or theother (use an arrow pointing to the circledcenter to indicate). Youshould also circle the doublebonds to which E or Z canbe assigned, and label themalso. A few of the carbons are numberedbecause they will be referred to in the next question.

(b) In the structure drawn above, carbons 16-19 are indicated with numerals. The conformation of the carbon-18/carbon-19 bond was also reported by these authors. These are the features of that conformational study:

1918

1716

(i) the "OH" group at carbon-18 is gauche to the "C=O" group attached to carbon-19. The C=O group may be abbreviated as "COR".(ii) the carbon chain that begins at carbon-17 is anti to the "C=O" group at carbon-19. The carbon chain that begins at carbon-17 may be abbreviated as "R".

Given these data, draw a Newman projection for the groups around the carbon-18 to carbon-19 bond as viewed from carbon-18 as the front atom and carbon-19 as the back atom.

B. (a) Provide a structural drawing for 1S, 2S-1,2-dibromo-1-methylcyclopentane (Compound Q).

(b) How many optically active diastereomers does Compound Q have?

(e) If the 1R,2S isomer has an specific rotation of -38Þ and the 1R,2R-isomer has an specific rotation of +24Þ, what is the specific rotation of Compound Q?

(f) How many meso stereoisomers are there for the connectivity represented by Compound Q?

24

4

6

2

2

2

www.umich.edu/~chem210

Second semester project

www.umich.edu/~chemh215

Second semester project

www.umich.edu/~chemh215

(1) 6 groups of 15-18 get a different article(2) each group becomes 5-6 subgroups of 3(3) each subgroup of 3 “owns” a step in sequence

- represent mechanism (static & animate)- correlate NMR spectra with structure- analyze experimental procedure

(4) make pedagogical choices to present ideas- in oral presentations- in writing- on web

Assessment of Student Learning

I. Exams, Papers, etc. (Product, no Path)

II. Periodic sampling (Product & Path)

III. Peer-based editing (Guided reflection;“editors”)

IV. Performance-based (Expert &/ Control)

V. Large-scale survey (Change & Correlation)

VI. Interview &/ Observe (Multiple sources)

Heady, J. E.; Coppola, B. P.; Titterington, L. C. "Assessment Standards." In, Siebert, E. D.; McIntosh, W. J., Eds. College Pathways to the Science Education Standards Arlington, VA: NSTA Press, 2001, 57-63.

Performance-based Assessment:The counter-intuitive event

Goal: to compare the skills of students who engage in weekly discussions where "student answers" are the beginning, not the end, of an academic conversation.

Method: devise a task where it is relatively certain that a reasonable prediction based on familiar information will be made, and then present the experimental information that demonstrates the prediction is backwards (or otherwise incomplete; interview 2 student groups and an "expert" group, code and compare).

2Structured Study Groups

• impact on grades• impact on course climate• impact on first-year U experience• impact on persistence in science• impact on learning - counterintuitive event

1. Rank these 5 things.

C Si Ge Sn Pb

E

2Structured Study Groups

• impact on grades• impact on course climate• impact on first-year U experience• impact on persistence in science• impact on learning - counterintuitive event

1. Rank these 5 things.

C Si Ge Sn Pb

Ethe natural prediction

2Structured Study Groups

• impact on grades• impact on course climate• impact on first-year U experience• impact on persistence in science• impact on learning - counterintuitive event

1. Rank these 5 things.

C Si Ge Sn Pb

E

2. Here are the experimental data.

Substituent X in -X(CH )

0

1

2

3

4

5

Si Sn

C

SiGe

SnPb

PbGeC

3 3

the natural prediction

Coding the interviews

0 5 10 15 20 25 min

restate

S idS rank

chair confstericslengthorbital

reflect

predict

recognize

elaboratereflectelaboraterankreconcile

promptexptreftextauthoritycomputational

Page 1 turn the pagePage 2

inquiry prompt: "How would you test your ideas?"

“expert” solution(fac & grad who do not know the facts)

SSG students grouped 80% of the time with those like expert (this one: 100%).

A/B+ non-SSG grouped10% of the time withthose like expert(this one: 0%)

Next generation?

• Problem: expansion of multimedia component to larger group of less skilled students

• Solutions: dedicated software & environment– > Studio instructional environment– > ChemSense (www.ChemSense.org)

• SRI collaboration (R. Kozma, E. Coleman, P. Schank)• integration into a new high school text project

– B. P. Coppola, J. S. Krajcik, A. Kiste, authors (WH Freeman)

– > LERN-IT modules

THEN

SOON

Lecture meets3x1hr, lab anddiscussion areseparate

Lecture meets1hr, lab anddiscussion aretogether 2x3hr

www.chemsense.org

Student & Teacher-generated work

QuickTime™ and aAnimation decompressor

are needed to see this picture.

Student & Teacher-generated work

QuickTime™ and aAnimation decompressor

are needed to see this picture.

QuickTime™ and aAnimation decompressor

are needed to see this picture.

PCK-guided design of Instructional Technology - a hypothesis

Bruner (1966) - neo-constructivist theory of learning that accounted for student & teacher & subject

• learner predisposition/readiness• intrinsic structure/organization of knowledge• effectiveness of sequence/pacing

readiness => learner

classroom pedagogy

PCK-guided design of Instructional Technology - a hypothesis

Bruner (1966) - neo-constructivist theory of learning that accounted for student & teacher & subject

• learner predisposition/readiness• intrinsic structure/organization of knowledge• effectiveness of sequence/pacing

readiness => learner

classroom pedagogy

PCK-guided design of Instructional Technology - a hypothesis

Bruner (1966) - neo-constructivist theory of learning that accounted for student & teacher & subject

• learner predisposition/readiness• intrinsic structure/organization of knowledge• effectiveness of sequence/pacing

readiness => learner

classroom pedagogy

readiness => subject/learner

?

LERN-ITLecture-Enhanced Reflective Normalization using Instructional Technology

Pre-lecture: mastery learning objective A “director’s cut” on focused (PCK) topicsPunctuated repeatable narrative according to intrinsic subject sequenceAnnually updated literature-based tasks for individual/group workAnnotated multiple representations

hypothesisposes aquestion:

subtextsubtextsubtextsubtextsubtextsubtextsubtextsubtextsubtextsubtextsubtext

In Chemistry, we understand better than nearly every other discipline how to create teams of undergraduate, graduate, and post-doctoral students in order to advance research goals. This is our model of professional development...

…and it begins with the design of undergraduate courses,where the potential to carry out research is first identified.

The same model of professional development can advance how teaching and learning are done.

3CSIE: Chemical Sciences at the Interface of

Education

Or, “how can faculty members add this sort of work to their alreadyoverfilled list of responsibilities?”

• coursework that identifies potential

• early entry into design, implementation, documentation, & assessment

• increased independence• intensive study

- coursework- seminars- projects- collaboration

• functional independence• professional readiness

• transferability

• faculty lines

underg

raduate

gra

duate

post

doc

Boyer, 1990: “a broadened conception of scholarship”

Coppola, 1994: broaden the infrastructure that works so well

Standards of literacy outside one’s core area

• functional literacy in areas of participation

• minimum level of competency in aligned areas of professional responsibility

• integrated understanding and demonstrated performance in interdisciplinary emergent areas

train

ing g

rants

1994

1998

2002

1991

CSIE: Graduate Program(future faculty education with a training grant model)

• 1998 - date:– US DOE GAANN supports 8-12/yr (mid-1 to mid-2)– 2 courses (1 used as cognate) in education– external/internal speaker & brown-bag series– propose & carry out a project in the department– on-campus collaboration– off-campus collaboration

• Other activities:– presentations at professional meetings, & institutional seminars,

workshops– publications– Increased grad student governance in general

• 2002 - date:– thesis chapters; combined PhD degree

CSIE: Graduate Program(actual chem PhD students)

Brett Duersch (BS BYU)

Sept-Dec 1998• enter UM PhD program• regular GSI training• begin: CSIE external speaker series• begin: CSIE brown-bag sessions

Jan-Dec 1999

Jan-Aug: CSIE fellowship• take 2 education cognate courses• design CSIE project• present at Wakonse conference

Sept-Dec: 50% CSIE fellow/50% GSI• implement CSIE project• co-run external speaker series (1 yr)

Jan-Dec 2000• assess CSIE project• present at Nat Assoc Res Sci Teach, Biennial

Chem Ed, & Amer Chem Soc Confs• modify GSI training program• CANDIDACY EXAM INCLUDES CSIE

Jan-Dec 2001

• JCST paper prepared

• seminar presentation at Notre Dame

Jan-Dec 2002

• JCST paper submitted

• prepare and submit JRST paper

• extend modified GSI training

Jan-May 2003

• May: Chemistry PhD

- 5 chapters: solid state NMR

- 2 chapters: CSIE

• JCST paper accepted

Th

e P

hD

stu

den

ts

NEW REACTIONS OF GERMYLENES WITH KETONESAND

ASSESSMENT OF STUDIO GENERAL CHEMISTRY

Ryan D. SweederA dissertation submitted in partial fulfillment

of the requirements for the degree of Doctor of Philosophy

(Chemistry)in The University of Michigan

2003

Doctoral Committee:Professor Mark M. Banaszak Holl, ChairProfessor Arthur J. Ashe, IIIProfessor Brian P. Coppola Professor Joseph S. Krajcik Professor Omar M. Yaghi

Th

e P

hD

stu

den

ts

Chapter I. IntroductionChapter II. Conversion of Phenones to Conjugated Trienes Via

Germylene CycloadditionChapter III. Germylene Reactions with QuinonesChapter IV. Activation and Catalytic Partial Hydrogenation of

BenzophenoneChapter V. Exploring Two Reactions of Ketones with

Ge[CH(SiMe3)2]2: CH and OH Insertion

Chapter VI. Development of Studio ChemistryChapter VII. Equilibrium Study in Studio General Chemistry Chapter VIII. Student Attitudes Toward Studio Chemistry

Ryan D. Sweeder - Table of Contents

2003 & beyond...

Department of Chemistry• integration into long-range planning• resource allocation• graduate student & faculty recruitment

University of Michigan• preliminary discussion for large scale fund-raising

* hire a group of faculty members?* include student support?

• international program * how to get creative work in

curriculum development in English?

China --- (MS/PhD) --- US

Thanks!

• US Department of Education - GAANNGraduate Assistantships in Areas of National Need

• University of Michigan Department of ChemistryCollege of LSACollege of LSA Honors programRackham Graduate School

• Carnegie Foundation for the Advancement of TeachingCarnegie Scholars programCarnegie Initiative on the Doctorate

• Research Corporation• Intel Corporation• NSF-PFF-ACS Phase 3