Biologically flavored "Organic First”:
a chemistry curriculum for the 21st century
RICHARD R. HARK
DEPARTMENT OF CHEMISTRY
JUNIATA COLLEGE
HUNTINGDON, PA 16652
2012 Biennial Conference on Chemical Education
THE PENNSYLVANIA STATE UNIVERSITY
“Chemistry and the Premedical Curriculum”
30 JULY 2012
WHO IS OUR AUDIENCE???
BIOLOGY MAJORS
PRE-HEALTH STUDENTS
CHEMISTRY and BIOCHEMISTRY
MAJORS
HOW TO BUILD A CURRICULUM
FOR ALL CONSTITUTENTS?
WOULD YOU CHOOSE THE TWO- SEMESTER
“GENERAL CHEMISTRY” APPROACH
OR
WOULD YOU FOCUS ON BIOLOGICALLYRELEVANT MATERIAL DRAWN LARGELY
FROM ORGANIC CHEMISTRY?
PROBLEMS WITH
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
PROBLEMS WITH
GENERAL CHEMISTRY
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.
ADVANTAGES 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 SOLVED
6.BIOLOGICALLY USEFUL CHEMISTRY COVERED FIRST
7. STUDENTS FIND OUT SOONER THAT THEIR STRENGTHS LIE
ELSEWHERE
8.FOCUSES ON CHEMISTRY THAT IS MORE RELEVANT TO THE
PRE-HEALTH CURRICULUM
PROBLEMS WITH THE
“NORMAL” ORGANIC COURSE
(WHENEVER IT IS TAUGHT)
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
JUNIATA’S SOLUTION
“BIOLOGICALLY FLAVORED”
ORGANIC FIRST
STARTED IN 1993
JUNIATA’S SOLUTION
A. CREATE A FRESHMAN
COURSE SET IN THE
CONTEXT OF BIOLOGICALLY
IMPORTANT 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
JUNIATA’S SOLUTION
B. CREATE SOPHOMORE LEVEL
COURSES TO BUILD ON
FRESHMAN COURSE, AND
COVER THE “GENERAL CHEM”
MATERIAL NOT COVERED
IN THE FRESHMAN COURSE
JUNIATA’S SOLUTION
C. CREATE JUNIOR LEVEL
COURSE TO TREAT ASPECTS
OF ORGANIC LEFT OUT
OF THE FRESHMAN COURSE
REQUIRED OF ALL
CHEMISTRY MAJORS
ALMOST NO ONE ELSE IN IT—
THINK WHAT YOU
COULD ACCOMPLISH!
A. OUR FRESHMAN COURSE
“ORGANIC 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
OMISSIONS
Diels-Alder Reaction
Least Hindered Approach of Reagents
Wittig Reaction and Other Ylids
Wolf-Kishner, Clemmenson
Organolithium Chemistry
Organocopper Chemistry
Diazomethane
Acid-catalyzed Aldols
OMISSIONS
Baeyer-Villiger Reaction
Permanganate Oxidations
Osmium Tetroxide Oxidations
Periodate Oxidations
Gabriel Synthesis
Nitrile Chemistry
Carbenes
Pericyclic Reactions
OMISSIONS
Free Radical Halogenation (NBS)
Free Radical Additions
Borane Additions
Peroxide Workup of Ozonolysis
Diazonium Salts
Nucleophilic Aromatic Substitution
Silyl Protecting Groups
Polymers
INCORPORATING BIOCHEMISTRY
SEMESTER I
Week 3:
Week 6:
Week 10:
Week 13:
H-bonding
Protein Structure
DNA Structure
Lipid bilayers
Charges at Physiological pH
Cholesterol Biosynthesis from Squalene
Chemistry of Vision
INCORPORATING BIOCHEMISTRY
SEMESTER II
Week 1:
Week 5:
Week 6:
Week 10:
Week 11:
Week 13:
Intrinsic Asymmetry of Nature
Disulfide Bonds in Protein Structure;
Phosphates as Nature’s Leaving Groups
Benzpyrene Epoxide
NAD as Biological Redox Agent
Carbohydrates
Glycolysis/TCA Cycle
Amino Acid Synthesis
Peptide Synthesis on Ribosome
Protein Structure: 1o, 2o, 3o
DNA Structure; Heme
B. OUR SOPHOMORE OFFERINGS
1. FALL SEMESTER
INTRODUCTORY INORGANIC CHEMISTRY
COVERS GENERAL AND INORGANIC MATERIAL
LEFT OUT OF “ORGANIC CHEMICAL CONCEPTS”
B. OUR SOPHOMORE OFFERINGS
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 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
C. OUR JUNIOR ORGANIC COURSE
“ORGANIC 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
SUMMARY OF COVERAGES
NON-CHEMISTRY MAJORS
1. LESS ORGANIC
SOONER
MORE TAILORED TO THEIR NEEDS
LESS IRRELEVANT MATERIAL
MORE RELEVANT MATERAIL
2. GENERAL CHEM
MORE SOPHISTICATED, MORE APPLIED
SUMMARY OF COVERAGES
CHEMISTRY MAJORS
1. MORE ORGANIC
2. SOME INORGANIC
3. MORE GRADUAL INTRODUCTION OF MATH
QUALITATIVE
QUANTITATIVE
MORE READY FOR P CHEM
4. CONSTANT REMINDERS THAT
BIOCHEMISTRY IS RELEVANT
SUMMARY OF COVERAGES
WHAT TEXTBOOK?
RESULTS
Year
2001
2002
2003
2004
2005
2006
2007
2008
2009
2010
2011
2012
Total
CHEMISTRY & BIOCHEMISTRY MAJORS
Grads
Grad
Professional
School
School
20
9
4
10
3
3
14
5
2
13
10
1
13
5
2
14
5
1
25
12
0
17
6
2
15
8
1
13
6
4
14
6
1
21
8
5
194
84
43%
26
13%
Note: most Juniata pre-health students are Biology majors.
RESULTS
COLLEGE WIDE
MCAT TEST SCORES
MED SCHOOL ADMISSION RATE
MED SCHOOL PERFORMANCE
NO SIGNIFICANT CHANGE
(95-100% ACCEPTANCE RATE)
CHEMISTRY GRADUATE SCHOOLS (2012):
Caltech, UNC, Rochester, OSU, Illinois
QUESTIONS?
Please contact me to get additional details
or to request a copy of the textbook:
hark@juniata.edu