green organic chemistry @ mt. sac by iraj nejad
TRANSCRIPT
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Green Organic Chemistry @ Mt. SAC
Mt. San Antonio College
Walnut, California
Iraj B. Nejad
210th 2YC3 Conference
Chemistry for a Sustainable Future
Kaneohe, Hawaii
May 22-23, 2015
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Mt. San Antonio College
n The largest single campus of the CA 112 Comm. College system-Located in the suburb of Los Angeles
n 40,000+ students, rich in diversity n Chemistry Department
v 11 Full-Time Faculty (15-18 Adjunct Faculty) v 45-50 Introductory Chemistry sections (CHEM 10, 20, 40) v 22-25 General Chemistry sections (CHEM 50 & 51) v 9-10 Organic Chemistry sections (CHEM 80 & 81) v 2300 - 2400 students per year Almost all students going through our program transfer to
Universities
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Chemistry Department Instrumentation & IT Facility
n 60 MHz Anasazi FT-NMR n HP 5890 GC/MS (not being utilized currently) n Perkin Elmer FT-IR (4, 2 brand new, equipped with the ATR
accessory for solid samples) n Varian AA n Gas Chromatographs (2) n Spartan Molecular Modeling Software (100 student License)
n IT Facility (30 networked facility w/instructor station) plus ~ 60 Additional computers/laptops for students use
n MeasureNet Data Collection System in Gen. Chem. Labs
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Green Chemistry at Mt. SAC
Ø Completing our fifth year of full Implementation in Organic Laboratory I & II
Ø Start? At the cCWCS Green Chemistry Workshop at the University of Oregon-Summer 2008
Ø Hendrix College, w/Tom Goodwin Summer 2009
Ø Result of my sabbatical project: 2009 –2010
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Green Chemistry at Mt. SAC
n Goal: Improve our Organic Lab Curriculum n Reduce waste n Save on the cost of lab textbook for students n Incorporate more Instrumentation & Computation in the
Labs
n Proposed: Test, Adapt and Implement 8-10 Green Labs in Organic Lab Curriculum
n Final Product: Two Green Chemistry Lab manuals (Resources: UO Workshop, GEMs, J. Chem. Ed., Hendrix College Labs)
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Green Chemistry at Mt. SAC
Ø Introduction to Green Chemistry
Ø Why green chemistry Ø What is green chemistry Ø Twelve Principles of green chemistry Ø Measures of Efficiency of a Reaction
Ø Introduction to IR Spectroscopy Ø Introduction to NMR Spectroscopy (1D/2D) Ø Introduction to Molecular Modeling (w/Spartan)
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Green Experiments (CHEM 80)
1. Biosynthesis of Ethanol from Molasses 2. Trimyristin: A Fat from Nutmeg 3. Isolation of Chlorophyll and Carotenoid Pigments
from Spinach 4. Identification of an Unknown Organic Compound 5. Structure and Nuclear Magnetic Resonance 6. Chemical Kinetics: Evidence for the SN1 Mechanism 7. Which Structural Isomer? (DEPT NMR) 8. The Nucleophilic Substitution Reaction (SN2)
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Green Experiments (CHEM 81)
1. A Green Solventless Diels – Alder Reaction 2. Diels – Alder Reaction in Water 3. Iodination of Salicylamide 4. Electrophilic Aromatic Substitution: Friedel-Crafts
Alkylation 5. Oxidation of Aromatic Aldehydes Using Oxone 6. A Solventless Aldol Condensation Reaction 7. Complete Assignment of Ibuprofen Structure (1D/
DEPT/HETCOR NMR) 8. Reductive Amination: Three Easy Pieces 9. Identification & Complete Assignment of an Unknown
Organic Structure (2D NMR - COSY)
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Computational Experiments Organic Chemistry I (CHEM 80) 1. Conformational Analysis (Open Chain Alkanes) 2. Conformational Analysis (Substituted Cyclohexanes) 3. Ring Strain in Cycloalkanes 4. Carbocation Stability 5. Regioselectivity of Electrophilic Addition to C = C Bond Organic Chemistry II (CHEM 81) 1. Aromatic Compounds 2. Heterocyclic Aromaticity 3. Electrophilic Aromatic Substitution (Reactivity Effect) 4. Electrophilic Aromatic Substitution (Directing Effect)
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Which Structural (C6 or C7) Isomer Introduction to 13C & DEPT NMR
Adapted from: Reeves and Chaney, JCE, 1998 Ø DEPT 13C NMR (Distortionless Enhancement by
Polarization Transfer) Ø distinguishes among carbon signals due to CH3, CH2, CH, and
quaternary carbons
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13C NMR of 2-Butanone
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DEPT NMR of 2-Butanone
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Pre-DEPT Quiz
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Post-DEPT Quiz
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Determination of Correct Structure (pre/post DEPT)
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SN2 Rxn - DMAP w/CH3I Which Nitrogen? (Hull, L.A., JCE 2001)
N
N(CH3)2
+ CH3I
DMAP
N
N(CH3)3
I
I
N
N(CH3)2
CH3
_
_
+
+
..
..
Prod A
Prod B
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DMAP Product 1H NMR
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DMAP product 13C NMR
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Computational Results
Product ΔHrxn (kJ) (PM3 method)
Ea (kJ)
Prod. A
678 321
Prod. B 563 ( -115 kJ )
258 ( - 63 kJ )
////////////////////////////////
Product B is the Thermodynamically preferred product.
Product B is also the Kinetically preferred Product.
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DMAP ELPOT Surface
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DMAP Potential Surface
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Reductive Amination Experiment (Touchette, K.M, GEMs site)
ortho-vanillin para-toluidin Imine product Acetylated amine
O
NH
HCH3
O
O
OCH3OCH3
H
H
CH3
NH2 - H2ON
CH3
COH3C
OHH3CO
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Imine Product Crystals
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Imine Product Crystals
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Reductive Amination Experiment Imine DEPT
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Reductive Amination Experiment Acetylated Amine DEPT
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Complete Assignment of Ibuprofen Structure
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Complete Assignment of Ibuprofen Structure (1H NMR Spectrum)
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Complete Assignment of Ibuprofen Structure (13C NMR Spectrum)
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Complete Assignment of Ibuprofen Structure (DEPT Spectrum)
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Complete Assignment of Ibuprofen Structure (HETCOR Spectrum)
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Group Work
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Green Chemistry at Mt. SAC
v Challenges v Time- Extensive… Search for, analyze, select,
pilot and finally implement appropriate labs
v Resources: Instrumentation, Computers and $$$
v Colleagues buy-in
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Green Chemistry at Mt. SAC
Outcome? Ø Still teaching organic chemistry but
within the context of green chemistry Ø Saving to College through waste reduction Ø Saving to students Ø Dynamic organic lab curriculum… new
green experiments can be tried and added to the curriculum at any time
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Acknowledgements
v Mt. San Antonio College v Deans Matt Judd & Larry Redinger v U. of Oregon Green Chemistry Workshop Leaders
(Jim Hutchison, Kenneth Doxsee, Julie Haack, all green chemistry Staff
v Tom Goodwin & his Staff at Hendrix College v Chemistry faculty at several US institutions who graciously
shared their green materials with me v My Colleagues in the Chemistry Department v Student assistants Stella Hartono, Vivian Le, Yingqiu Zhang v CHEM 80/81 students - 2009 & 2010 v National Science Foundation