Biologically flavored "Organic First”:Biologically flavored "Organic First”:a chemistry curriculum for the 21st centurya chemistry curriculum for the 21st century

RICHARD R. HARKRICHARD R. HARKDEPARTMENT OF CHEMISTRYDEPARTMENT OF CHEMISTRY

JUNIATA COLLEGEJUNIATA COLLEGEHUNTINGDON, PA 16652HUNTINGDON, PA 16652

2012 Biennial Conference on Chemical Education2012 Biennial Conference on Chemical EducationTHE PENNSYLVANIA STATE UNIVERSITYTHE PENNSYLVANIA STATE UNIVERSITY

““Chemistry and the Premedical Curriculum” Chemistry and the Premedical Curriculum”

30 JULY 201230 JULY 2012

WHO IS OUR AUDIENCE???WHO IS OUR AUDIENCE???

BIOLOGY MAJORSBIOLOGY MAJORS

PRE-HEALTH STUDENTSPRE-HEALTH STUDENTS

CHEMISTRY and BIOCHEMISTRYCHEMISTRY and BIOCHEMISTRYMAJORSMAJORS

HOW TO BUILD A CURRICULUM HOW TO BUILD A CURRICULUM

FOR ALL CONSTITUTENTS?FOR ALL CONSTITUTENTS?

WOULD YOU CHOOSE THE TWO- SEMESTER WOULD YOU CHOOSE THE TWO- SEMESTER “GENERAL CHEMISTRY” APPROACH“GENERAL CHEMISTRY” APPROACH

OR OR WOULD YOU FOCUS ON BIOLOGICALLY-WOULD YOU FOCUS ON BIOLOGICALLY-RELEVANT MATERIAL DRAWN LARGELY RELEVANT MATERIAL DRAWN LARGELY

FROM ORGANIC CHEMISTRY?FROM ORGANIC CHEMISTRY?

PROBLEMS WITH PROBLEMS WITH

GENERAL CHEMISTRY GENERAL CHEMISTRY

1. STUDENTS HAVE VERY DIFFERENT LEVELS OF PREPARATION

2. MANY STUDENTS HAVE SEEN MUCH OF THE MATERIAL BEFORE

AND MAY BE BORED AT SEEING IT AGAIN

3. MANY STUDENTS HAVE DIFFICULTY WITH THE MATH REQUIRED

4. TOO DISJOINTED

5. STUDENTS ARE ASKED TO MANIPULATE EQUATIONS DEALING

WITH MOLECULES BEFORE THEY UNDERSTAND WHAT

MOLECULES ARE

THESE PROBLEMS ARE WELL-KNOWN, WIDELY DISCUSSED AND

ARE BEING ADDRESSED IN CLEVER WAYS.

TEACHING AN ORGANIC COURSE FIRST IS AN APPROACH THAT SOLVES MOST

OF THESE PROBLEMS.

PROBLEMS WITH PROBLEMS WITH GENERAL CHEMISTRY GENERAL CHEMISTRY

ADVANTAGES OF ORGANIC FIRSTADVANTAGES OF ORGANIC FIRST

1. COURSE HOLDS TOGETHER—EVERYTHING BUILDS ON WHAT CAME PREVIOUSLY

2. GIVES STUDENTS A QUALITATIVE FEEL FOR MOLECULES BEFORE APPLYING MATH

3. MATH DELAYED UNTIL SOPHOMORE YEAR, WHEN STUDENTS ARE (PERHAPS) MORE MATHEMATICALLY SOPHISTICATED

4. WITH FEW EXCEPTIONS, STUDENTS ARE EQUALLY UNFAMILIAR WITH THE MATERIAL

5. TOPICS SUCH AS HYBRIDIZATION, KINETICS, AND EQUILIBRIUM CAN BE PRESENTED IN A CONTEXT AND USED IMMEDIATELY RATHER THAN BEING PRESENTED AS ABSTRACT PROBLEMS TO BE SOLVED6.BIOLOGICALLY USEFUL CHEMISTRY COVERED FIRST7. STUDENTS FIND OUT SOONER THAT THEIR STRENGTHS LIE

ELSEWHERE8.FOCUSES ON CHEMISTRY THAT IS MORE RELEVANT TO THE PRE-HEALTH CURRICULUM

1. MOST STUDENTS TAKING ORGANIC ARE NOT CHEMISTS, YET

WE TEACH THEM MATERIAL ONLY CHEMISTS NEED TO KNOW

2. MOST STUDENTS TAKING ORGANIC ARE NOT CHEMISTS, YET

WE DO NOT TEACH THEM MATERIAL THEY DO NEED TO

KNOW

3. CANNOT ASSUME “GENERAL CHEM” MATERIAL, NORMALLY

“REVIEWED” IN FIRST CHAPTER/WEEK--MUST BE TAUGHT AS IF

NEW

4. WEEKS SPENT TEACHING BACKGROUND DETRACTS FROM

MATERIAL YOU CAN COVER IN AN ORGANIC COURSE

PROBLEMS WITH THEPROBLEMS WITH THE““NORMALNORMAL”” ORGANIC COURSE ORGANIC COURSE

(WHENEVER IT IS TAUGHT)(WHENEVER IT IS TAUGHT)

JUNIATAJUNIATA’’S SOLUTION S SOLUTION

“BIOLOGICALLY FLAVORED” “BIOLOGICALLY FLAVORED” ORGANIC FIRSTORGANIC FIRST

STARTED IN 1993STARTED IN 1993

A. CREATE A FRESHMAN A. CREATE A FRESHMAN COURSE SET IN THE COURSE SET IN THE

CONTEXT OF BIOLOGICALLY CONTEXT OF BIOLOGICALLY IMPORTANT ORGANIC CHEMISTRYIMPORTANT ORGANIC CHEMISTRY

CATER DELIBERATELY TO THE BIOLOGISTS AND PRE-HEALTH STUDENTS

LEAVE OUT A SIGNIFICANT AMOUNT OF “NORMAL” ORGANIC CHEMISTRY

DO “NO HARM” TO THE CHEMISTRY MAJORS

JUNIATAJUNIATA’’S SOLUTIONS SOLUTION

B. CREATE SOPHOMORE LEVEL B. CREATE SOPHOMORE LEVEL

COURSES TO BUILD ON COURSES TO BUILD ON FRESHMAN COURSE, AND FRESHMAN COURSE, AND

COVER THE COVER THE ““GENERAL CHEMGENERAL CHEM”” MATERIAL NOT COVERED MATERIAL NOT COVERED

IN THE FRESHMAN COURSEIN THE FRESHMAN COURSE

JUNIATAJUNIATA’’S SOLUTIONS SOLUTION

C. CREATE JUNIOR LEVEL C. CREATE JUNIOR LEVEL COURSE TO TREAT ASPECTS COURSE TO TREAT ASPECTS

OF ORGANIC LEFT OUT OF ORGANIC LEFT OUT OF THE FRESHMAN COURSEOF THE FRESHMAN COURSE

REQUIRED OF ALL CHEMISTRY MAJORS

ALMOST NO ONE ELSE IN IT—THINK WHAT YOU

COULD ACCOMPLISH!

JUNIATAJUNIATA’’S SOLUTIONS SOLUTION

A. OUR FRESHMAN COURSEA. OUR FRESHMAN COURSE““ORGANIC CHEMICAL CONCEPTSORGANIC CHEMICAL CONCEPTS””

1. FULL YEAR COURSE

2. BEGIN AT THE FRESHMAN LEVEL

3. LEAVE OUT BIOLOGICALLY IRRELEVANT MATERIAL

4. INCLUDE BIOLOGICALLY RELEVANT MATERIAL

OFTEN OMITTED--INTEGRATED AS MUCH AS

POSSIBLE, RATHER THAN SEQUESTERED AT THE END

Diels-Alder ReactionLeast Hindered Approach of Reagents

Wittig Reaction and Other YlidsWolf-Kishner, ClemmensonOrganolithium ChemistryOrganocopper Chemistry

DiazomethaneAcid-catalyzed Aldols

OMISSIONS

Baeyer-Villiger ReactionPermanganate Oxidations

Osmium Tetroxide OxidationsPeriodate Oxidations

Gabriel SynthesisNitrile Chemistry

CarbenesPericyclic Reactions

OMISSIONS

OMISSIONS

Free Radical Halogenation (NBS)Free Radical Additions

Borane AdditionsPeroxide Workup of Ozonolysis

Diazonium SaltsNucleophilic Aromatic Substitution

Silyl Protecting GroupsPolymers

INCORPORATING BIOCHEMISTRYINCORPORATING BIOCHEMISTRY

SEMESTER I

Week 3: H-bonding Protein Structure

DNA StructureLipid bilayers

Week 6: Charges at Physiological pHWeek 10: Cholesterol Biosynthesis from SqualeneWeek 13: Chemistry of Vision

INCORPORATING BIOCHEMISTRYINCORPORATING BIOCHEMISTRY

SEMESTER II

Week 1: Intrinsic Asymmetry of NatureWeek 5: Disulfide Bonds in Protein Structure;

Phosphates as Nature’s Leaving GroupsBenzpyrene Epoxide

Week 6: NAD as Biological Redox AgentCarbohydrates

Week 10: Glycolysis/TCA CycleWeek 11: Amino Acid Synthesis

Peptide Synthesis on Ribosome Protein Structure: 1o, 2o, 3o

Week 13: DNA Structure; Heme

B. OUR SOPHOMORE OFFERINGSB. OUR SOPHOMORE OFFERINGS

1. FALL SEMESTER INTRODUCTORY INORGANIC CHEMISTRY

COVERS GENERAL AND INORGANIC MATERIAL LEFT OUT OF “ORGANIC CHEMICAL CONCEPTS”

2. SPRING SEMESTER

ANALYTICAL CHEMISTRY

QUANTITATIVELY RIGOROUS TREATMENT OF MATERIAL USUALLY TAUGHT IN GENERAL

CHEMISTRY, BUT NOW TO STUDENTS WITH BETTER MATH BACKGROUNDS AND,

MOST IMPORTANTLY, A CHEMICAL CONTEXT IN WHICH TO UNDERSTAND THE MATERIAL.

HEAVY EMPHASIS ON MODERN INSTRUMENTATION

POSSIBLE FUTURE PLANS: THIS COURSE WILL BE MOVED TO THE JUNIOR YEAR TO BECOME A MORE

TRADITIONAL INSTRUMENTAL METHODS COURSE FOR CHEMISTRY MAJORS AND WILL BE REPLACED WITH AN

INTRODUCTORY BIOCHEMISTRY COURSE

B. OUR SOPHOMORE OFFERINGSB. OUR SOPHOMORE OFFERINGS

3. SPRING SEMESTER, FOR CHEMISTS:

INTERMEDIATE INORGANIC CHEMISTRY

COVERS INORGANIC MATERIAL LEFT OUT OF “ORGANIC CHEMICAL CONCEPTS”

CAN GO FURTHER THAN GENERAL CHEMISTRY USUALLY DOES

A REAL INORGANIC COURSE BEFORE THE JUNIOR YEAR

ADVANCED INORGANIC STILL AVAILABLE AS AN UPPER LEVEL ELECTIVE

B. OUR SOPHOMORE OFFERINGSB. OUR SOPHOMORE OFFERINGS

C. OUR JUNIOR ORGANIC COURSEC. OUR JUNIOR ORGANIC COURSE

““ORGANIC REACTIONSORGANIC REACTIONS””1. FILL IN MATERIAL LEFT OUT OF “ORGANIC CHEMICAL CONCEPTS”

2. STUDENTS HAVE SEEN ORGANIC BEFORE, AND HAD

SOME TIME TO DIGEST IT

3. GREATER EMPHASIS ON SYNTHESIS AND MECHANISM

4. MUCH SMALLER CLASS, PRIMARILY ONLY CHEM MAJORS

5. CAN GO FURTHER THAN SOPHOMORE ORGANIC USUALLY DOES

6. ALL CHEM MAJORS GET A SECOND, MORE MATURE DOSE OF

ORGANIC

7. NO NEED TO DRAG BIOLOGY STUDENTS KICKING AND SCREAMING

THROUGH SYNTHETIC REACTIONS

1. LESS ORGANIC

SUMMARY OF COVERAGESSUMMARY OF COVERAGES

NON-CHEMISTRY MAJORS

SOONERMORE TAILORED TO THEIR NEEDSLESS IRRELEVANT MATERIALMORE RELEVANT MATERAIL

2. GENERAL CHEM

MORE SOPHISTICATED, MORE APPLIED

1. MORE ORGANIC

SUMMARY OF COVERAGESSUMMARY OF COVERAGES

CHEMISTRY MAJORS

3. MORE GRADUAL INTRODUCTION OF MATH

QUALITATIVE QUANTITATIVE

4. CONSTANT REMINDERS THAT BIOCHEMISTRY IS RELEVANT

2. SOME INORGANIC

MORE READY FOR P CHEM

SUMMARY OF COVERAGESSUMMARY OF COVERAGES

WHAT TEXTBOOK?WHAT TEXTBOOK?

RESULTSRESULTSCHEMISTRY & BIOCHEMISTRY MAJORS

Year Grads Grad Professional School School

2001 20 9 42002 10 3 32003 14 5 22004 13 10 12005 13 5 22006 14 5 12007 25 12 02008 17 6 22009 15 8 12010 13 6 42011 14 6 12012 21 8 5

Total 194 84 2643% 13%

Note: most Juniata pre-health students are Biology majors.

RESULTSRESULTS

COLLEGE WIDE

MCAT TEST SCORESMED SCHOOL ADMISSION RATEMED SCHOOL PERFORMANCE

NO SIGNIFICANT CHANGE

(95-100% ACCEPTANCE RATE)

CHEMISTRY GRADUATE SCHOOLS (2012):Caltech, UNC, Rochester, OSU, Illinois

QUESTIONS?QUESTIONS?

Please contact me to get additional details or to request a copy of the textbook:

hark@juniata.edu