Welcome to the Green Chemistry Journal Abstracts page!  Here you will find a large collection of hand-sorted green chemistry education journal articles that focus primarily on green chemistry laboratory experiments. Below you will find the journals' article information including titles, authors, abstracts, and journal references.  Check back often for the latest green chemistry journal abstract updates!

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Journal of Chemical Education              The Chemical Educator

Green Chemistry and Education

Dennis L. Hjeresen
The Green Chemistry Institute, Los Alamos National Laboratory, Los Alamos, NM 87545

Janet M. Boese
Division of Education and International Activities, American Chemical Society, 1155 Sixteenth Street, NW, Washington, DC 20036

David L. Schutt
ACS Office of Legislative and Government Affairs, 1155 Sixteenth Street, NW, Washington, DC 20036

J. Chem. Educ., 2000, 77 (12), p 1543
DOI: 10.1021/ed077p1543
Publication Date (Web): December 1, 2000

 Abstract
Many students today are profoundly interested in the sustainability of their world. With growing public concern over global warming and greenhouse gases, students want to understand how human actions affect the health of our planet. Students are deeply concerned about pollution. They practice recycling. Moreover, they want to secure a healthy Earth for future generations. As students of chemistry, they have a unique opportunity to start at the ground floor of the exciting and expanding field of green chemistry.

Keywords:
Curriculum
Green Chemistry

 

Microwave Instruments: Green Machines for Green Chemistry?

Edward P. Zovinka* and Anne E. Stock
Department of Chemistry, Saint Francis University, Loretto Pennsylvania 15940
*ezovinka@francis.edu

 J. Chem. Educ., 2010, 87 (4), pp 350–352
DOI: 10.1021/ed800150e
Publication Date (Web): March 9, 2010

Abstract
In this column, the authors discuss the ease of using microwave ovens for various activities in the undergraduate chemistry laboratory and suggest a few models of microwave systems for readers to consider.

Keywords:
First-Year Undergraduate/General; High School/Introductory Chemistry
Environmental Chemistry; Laboratory Instruction
Instrumental Methods

 

Topics in Green Chemistry

Mary M. Kirchhoff
Green Chemistry Institute, American Chemical Society, Washington, DC 20036

 J. Chem. Educ., 2001, 78 (12), p 1577
DOI: 10.1021/ed078p1577
Publication Date (Web): December 1, 2001 

Abstract
This is the mission statement for the feature column, Topics in Green Chemistry.

Keywords:
General Public
Environmental Chemistry Report
Green Chemistry

 

Why cupric chloride crystals are green

Felix Sabba and Craig Zebrowski

 J. Chem. Educ., 1986, 63 (12), p 1091
DOI: 10.1021/ed063p1091
Publication Date: December 1986

Abstract
A demonstration to explain the color differences between copper chloride and copper sulfate.

Keywords:
Demonstrations
Tested Demonstrations
Coordination Compounds

 

An Approach Towards Teaching Green Chemistry Fundamentals

Susan D. Van Arnum
Chemistry Department, Union County College, Cranford, NJ 07016

J. Chem. Educ., 2005, 82 (11), p 1689
DOI: 10.1021/ed082p1689
Publication Date (Web): November 1, 2005 

Abstract
One principle of green chemistry is the elimination of waste in chemical processes prior to its generation. For this dry laboratory, a procedure for the nitrosation of 2,5-hexanedione is evaluated using a recently described metrics system. Since the reaction conditions for the synthesis of 3-acetyl-5-methylisoxazole are solvent-free and the process utilizes catalytic chemistry, this experiment concentrates on an analysis of the impact of auxiliary substances such as extraction solvents and separation agents as sources of waste in chemical processes. The importance of yield improvement as it relates to waste minimization is also highlighted. 

Keywords:
Second-Year Undergraduate
Environmental Chemistry
Green Chemistry

 

News from Online: Green Chemistry

Erich S. Uffelman
Department of Chemistry, Washington and Lee University, Lexington, VA 24450

 J. Chem. Educ., 2004, 81 (2), p 172
DOI: 10.1021/ed081p172
Publication Date (Web): February 1, 2004

 Abstract
An introductory, non-exhaustive set of online resources is presented to provide readers with an entry into the area of green chemistry.

 Keywords:
High School / Introductory Chemistry
Curriculum
News From Online
Internet / Web-Based Learning
Green Chemistry

 

Some Exercises Reflecting Green Chemistry Concepts

Yu-min Song , Yong-cheng Wang and Zhi-yuan Geng
Department of Chemistry, Northwest Normal University, Lanzhou, 730070, China

 J. Chem. Educ., 2004, 81 (5), p 691
DOI: 10.1021/ed081p691
Publication Date (Web): May 1, 2004

 Abstract
Three exercises related to green chemistry are presented. In the first exercise students compare two methods to prepare aluminum hydroxide and find a new method that can save more feedstock. The second exercise has students selecting a process that reflects the atom economy concept in three methods of preparing Cu(NO3)2. In the third exercise students determine the most reasonable ratio of stoichiometry map for maximum utilization of FeS to prepare Na2S2O3•5H2O. Through these exercises, students learn the effect of green chemistry concepts.

 Keywords:
High School / Introductory Chemistry
Environmental Chemistry
Green Chemistry

 

Introducing Green Chemistry in Teaching and Research

Terrence J. Collins
Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, PA 15213

 J. Chem. Educ., 1995, 72 (11), p 965
DOI: 10.1021/ed072p965
Publication Date: November 1995

 Abstract
In the midst of a more vigorous concern for the environment, several terms have been put forward to capture an important idea. They represent the supposition that chemical processes that carry environmental negatives can be replaced with less polluting or nonpolluting alternatives. Here the term "green chemistry" will be the focus since it is now the most widely used term. The principles of green chemistry that can energize our classrooms and bring long-term meaning and direction to a component of academic research await clear definition. This article suggests key elements for both the research and the teaching components.

 Keywords:
First-Year Undergraduate / General
Environmental Chemistry
Symposium Report
Green Chemistry

 

Microscale Chemistry and Green Chemistry: Complementary Pedagogies

Mono M. Singh , Zvi Szafran and R. M. Pike
National Microscale Chemistry Center , and Chemistry Department, Merrimack College, North Andover, MA 01845

 J. Chem. Educ., 1999, 76 (12), p 1684
DOI: 10.1021/ed076p1684
Publication Date (Web): December 1, 1999

 Abstract
This paper describes the complementary nature of microscale chemistry and green chemistry. Green chemistry emphasizes the concepts of atom economy, source reduction, pathway modification, solvent substitution, and pollution prevention as means of improving the environmental impact of industrial chemistry. Microscale chemistry serves as a tool for incorporating green chemistry ideas across the curriculum in educational institutions. Examples are drawn from microscale laboratory experiments to illustrate the pedagogic connection between the two areas.

 Keywords:
First-Year Undergraduate / General
Laboratory Instruction
The Microscale Laboratory
Microscale Lab

 

Ionic Liquids and Green Chemistry: A Lab Experiment

Annegret Stark*, Denise Ott, Dana Kralisch, Guenter Kreisel and Bernd Ondruschka
Institute for Technical Chemistry and Environmental Chemistry, Friedrich-Schiller University of Jena, Lessingstrasse 12, 07743 Jena, Germany
*annegret.stark@uni-jena.de

 J. Chem. Educ., 2010, 87 (2), pp 196–201
DOI: 10.1021/ed8000396
Publication Date (Web): January 12, 2010

 Abstract
Although ionic liquids have been investigated as solvents for many applications and are starting to be used in industrial processes, only a few lab experiments are available to introduce students to these materials. Ionic liquids have been discussed in the context of green chemistry, but few investigations have actually assessed the degree of their greenness. This experiment combines two research areas, ionic liquids and ecological assessment, in an advanced undergraduate lab course. The modular combination of these two research areas allows for the adaptation of the timetable and content. Two ionic liquids are synthesized, and the method of heating (microwave-assisted vs convective), temperature, time, and alkylating agent are varied. In addition to the yield, simple metrics (atom economy, reaction mass efficiency, E-factor) in combination with energy efficiency, prices of chemicals, and ecological impacts of the materials are considered. It is the goal of this experiment to help students realize that a synthetic method leading to quantitative yields is not a priori green: other factors (nature of reactants, energy consumption, etc.) must be assessed as well.

 Keywords:
Graduate Education/Research; Upper-Division Undergraduate
Demonstrations; Environmental Chemistry; Laboratory Instruction
Collaborative/Cooperative Learning; Hands-On Learning/Manipulatives; Inquiry-Based/Discovery Learning
Undergraduate Research; Green Chemistry; Nucleophilic Substitution; Synthesis

 

Completing Our Education. Green Chemistry in the Curriculum

Christopher Kitchens
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA 30332

Reagan Charney
Department of Chemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400

David Naistat
Department of Chemistry, University of Miami, Coral Gables, FL 33146

Jennifer Farrugia
Department of Chemistry, Michigan State University, East Lansing, MI 48824

Andres Clarens
Environmental Engineering, University of Michigan, Ann Arbor, MI 48109

Adam O'Neil
Department of Polymer Science and Engineering, University of Massachusetts, Amherst, MA 01003

Carmen Lisowski
Department of Chemistry, University of Oregon, Eugene, OR 97403

Birgit Braun
Department for Chemical Engineering, Colorado School of Mines, Golden, CO 80401

 J. Chem. Educ., 2006, 83 (8), p 1126
DOI: 10.1021/ed083p1126
Publication Date (Web): August 1, 2006

 Abstract
This Commentary resulted from a series of conversations between an international group of chemistry and chemical engineering graduate students from the 3rd Annual ACS Green Chemistry Summer School, who reflected on their undergraduate education and discussed 1) the areas of green chemistry that were often neglected, 2) the value of integrating green chemistry principles in today's curricula, and 3) strategies educators might use to incorporate green chemistry in their classrooms. We have outlined areas of scientific knowledge that we believe to be of vital importance for the education of future chemists and engineers, as well as graduates of other disciplines including public relations, business, and public policy. Green Chemistry has the potential to recruit innovative and energetic students, repair a damaged public image, and bolster the long-term prosperity of the chemical sector on the domestic and international scale. Instead of eliminating existing courses, we argue that teaching traditional chemistry in a new way is the most effective way to achieve these ends. A new series of teaching principles and tools necessary to implement this change are discussed with emphasis on the long range impacts of a chemistry education that is inherently green.

 Keywords:
First-Year Undergraduate / General
Curriculum
Commentary
Green Chemistry

 

Introduction to Green Chemistry

Wheeler Conover
Southeast Community College, Cumberland, KY 40823

 J. Chem. Educ., 2003, 80 (3), p 268
DOI: 10.1021/ed080p268.1
Publication Date (Web): March 1, 2003

 Abstract
Introduction to the principles of green chemistry emphasizing waste reduction; includes laboratory activities.

 Keywords:
High School / Introductory Chemistry
Environmental Chemistry
Book and Media Reviews
Textbooks / Reference Books
Green Chemistry

 

Green Chemistry: An Introductory Text

Alan M. Rosan
Department of Chemistry, Drew University, Madison, NJ 07940

 J. Chem. Educ., 2003, 80 (10), p 1141
DOI: 10.1021/ed080p1141
Publication Date (Web): October 1, 2003

 Abstract
Employing many current, industrially significant examples, Green Chemistry examines waste minimization, environmental performance, catalysis, solvents, renewable resources, emerging technologies, the design of greener processes, and industrial case studies. The concluding chapter posits an integrated approach to a greener chemical industry.

 Keywords:
Upper-Division Undergraduate
Environmental Chemistry
Book and Media Reviews
Textbooks / Reference Books
Green Chemistry

 

Bringing State-of-the-Art, Applied, Novel, Green Chemistry to the Classroom by Employing the Presidential Green Chemistry Challenge Awards

Michael C. Cann
Department of Chemistry, University of Scranton, Scranton, PA 18510

 J. Chem. Educ., 1999, 76 (12), p 1639
DOI: 10.1021/ed076p1639
Publication Date (Web): December 1, 1999

 Abstract
The Presidential Green Chemistry Challenge (PGCC) Awards Program was initiated in 1995 by the Clinton administration. These awards offer a method of recognizing companies (or other institutions) or individuals for developing and demonstrating technologies or processes "that promote pollution prevention and industrial ecology through a new EPA Design for the Environment partnership with the chemical industry". In our environmental chemistry course at the University of Scranton, students select one of the winning entries from the most recent PGCC Awards competition and present a poster on the entry. This exercise exposes these students to state-of-the-art, applied, novel, green chemistry that they would be unlikely to encounter in any other course.

 Keywords:
First-Year Undergraduate / General
Curriculum
Learning Theories

 

A Green Polymerization of Aspartic Acid for the Undergraduate Organic Laboratory

George D. Bennett
Department of Chemistry, Millikin University, Decatur, IL 62522

 J. Chem. Educ., 2005, 82 (9), p 1380
DOI: 10.1021/ed082p1380
Publication Date (Web): September 1, 2005

 Abstract
B/pased on a technology that won a Presidential Green Chemistry Challenge Award, this experiment involves the thermal polymerization of aspartic acid and subsequent hydrolysis to give sodium poly(aspartate). The procedure is suitable for introducing students to the important topic of polymers and for illustrating several of the principles of green chemistry.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives

 

A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory

George D. Bennett
Department of Chemistry, Millikin University, Decatur, IL 62522

 J. Chem. Educ., 2006, 83 (12), p 1871
DOI: 10.1021/ed083p1871
Publication Date (Web): December 1, 2006

 Abstract
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment illustrates a number of principles of green chemistry while also revealing some of the trade-offs. This project also affords several opportunities for open-ended investigations.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Addition Reactions

 

A Green Alternative to Aluminum Chloride Alkylation of Xylene

Grigoriy A. Sereda and Vikul B. Rajpara
Department of Chemistry, University of South Dakota, Vermillion, SD 57069

 J. Chem. Educ., 2007, 84 (4), p 692
DOI: 10.1021/ed084p692
Publication Date (Web): April 1, 2007

 Abstract
We present a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst.

 Keywords:
High School / Introductory Chemistry
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Alkylation

 

Cocrystal Controlled Solid-State Synthesis. A Green Chemistry Experiment for Undergraduate Organic Chemistry

Miranda L. Cheney and Michael J. Zaworotko
Department of Chemistry, University of South Florida, Tampa, FL 33620

Steve Beaton and Robert D. Singer
Department of Chemistry, Saint Mary''s University, Halifax, Nova Scotia, Canada B3H 3C3

 J. Chem. Educ., 2008, 85 (12), p 1649
DOI: 10.1021/ed085p1649
Publication Date (Web): December 1, 2008

 Abstract
Green chemistry has become an important area of concern for all chemists from practitioners in the pharmaceutical industry to professors and the students they teach and is now being incorporated into lectures of general and organic chemistry courses. However, there are relatively few green chemistry experiments that are easily incorporated into these undergraduate courses and clearly demonstrate the application of green chemistry principles. Experiments are described that can be adapted to a typical undergraduate organic chemistry course easily and are inexpensive, relatively safe, require no solvent (or extremely small quantities of solvent), have high atom economy, make use of non-toxic or low toxicity compounds, and generate negligible quantities of waste. The experiments can be accomplished through the use of a new technique known as cocrystal controlled solid-state synthesis, C3S3. The method not only represents an area of current high activity in the scientific research community but also exposes students to the actual practice and application of green chemistry.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Amines / Ammonium Compounds

 

A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory

Eric Eby and S. Todd Deal
Department of Chemistry, Georgia Southern University, Statesboro, GA 30460

 J. Chem. Educ., 2008, 85 (10), p 1426
DOI: 10.1021/ed085p1426
Publication Date (Web): October 1, 2008

 Abstract
We developed an alternative electrophilic aromatic substitution reaction for the organic chemistry teaching laboratory. The experiment is an electrophilic iodination reaction of salicylamide, a popular analgesic, using environmentally friendly reagents—sodium iodide and household bleach. Further, we designed the lab as a guided-inquiry experiment, asking the students first to predict the orientation of the substitution reaction. After synthesizing the product, the students are asked to determine its structure using FT-IR spectroscopy. The choice of this method of characterization was intentional because of the utility of infrared spectroscopy in determining substitution patterns on aromatic rings and also because it requires students to analyze the fingerprint region of the spectrum. Given that most classroom instruction on IR focuses on functional group determination, we believe this is an added benefit to this experiment.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Aromatic Compounds

 

A Green Multicomponent Reaction for the Organic Chemistry Laboratory. The Aqueous Passerini Reaction

Matthew M. Hooper and Brenton DeBoef
Department of Chemistry, University of Rhode Island, Kingston, RI 02881-1966

 J. Chem. Educ., 2009, 86 (9), p 1077
DOI: 10.1021/ed086p1077
Publication Date (Web): September 1, 2009

 Abstract
Water is the ideal green solvent for organic reactions. However, most organic molecules are insoluble in it. Herein, we report a laboratory module that takes advantage of this property. The Passerini reaction, a three-component coupling involving an isocyanide, aldehyde, and carboxylic acid, typically requires ~ 24 h reaction times in organic solvents, but produces a quantitative conversion and yield in < 30 min when performed in water. This rate enhancement allows the Passerini reaction to be easily adapted for use in a second-year organic laboratory course. Additionally, the incorporation of this laboratory module facilitates discussions of both green chemistry and combinatorial chemistry in the curriculum.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Hands-On Learning / Manipulatives
Aqueous Solution Chemistry

 

Patterning Self-Assembled Monolayers on Gold. Green Materials Chemistry in the Teaching Laboratory

Lallie C. McKenzie , Lauren M. Huffman , Kathryn E. Parent and James E. Hutchison
Department of Chemistry and Materials Science Institute, Universty of Oregon, Eugene, OR 97403-1253

John E. Thompson
Department of Chemistry, Lane Community College, Eugene, OR 97405

 J. Chem. Educ., 2004, 81 (4), p 545
DOI: 10.1021/ed081p545
Publication Date (Web): April 1, 2004

 Abstract
Convenient laboratory exercises that demonstrate self-assembled monolayer (SAM) chemistry and organic thin-film patterning as examples of the applications of organic chemistry in materials chemistry and nanoscience are described. Students explore the properties of alkanethiol monolayers assembled on easily prepared, readily available, and inexpensive gold films on vinyl. Microcontact printing and ozone patterning are presented as two means of patterning monolayer films. The technological applications of these patterning methods in micro- and nanoelectronics are discussed. Students visualize these patterns by observing how water vapor condenses on patterns composed of hydrophobic and hydrophilic components. In addition to illustrating materials chemistry concepts, this laboratory exercise introduces a number of important green chemistry concepts. Specifically, the advantages of self-assembly methods and the benefits of using a monolayer in place of a thicker polymer film are described to show how green chemistry can be applied to the chemistry of materials.

 Keywords:
Second-Year Undergraduate
Environmental Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Materials Science

 

An Asymptotic Approach to the Development of a Green Organic Chemistry Laboratory

Thomas E. Goodwin
Department of Chemistry, Hendrix College, Conway, AR 72032

 J. Chem. Educ., 2004, 81 (8), p 1187
DOI: 10.1021/ed081p1187
Publication Date (Web): August 1, 2004

 Abstract
In recent years, we have striven to make our introductory microscale organic chemistry lab experiments more environmentally benign. We describe some philosophical questions and practical decisions that have guided the greening of our organic lab at Hendrix College, followed by brief descriptions of three exemplary green experiments.

 Keywords:
Second-Year Undergraduate
Curriculum
Green Chemistry

 

Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment

 Sam H. Leung and Stephen A. Angel
Department of Chemistry, Washburn University, Topeka, KS 66621

 J. Chem. Educ., 2004, 81 (10), p 1492
DOI: 10.1021/ed081p1492
Publication Date (Web): October 1, 2004

 Abstract
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry. This experiment can be extended to include 1H NMR analysis of the products. Students can observe the difference in the coupling constants of the alkenyl protons between the E and Z isomers of 1-(4-bromophenyl)-2-phenylethene.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Chromatography

 

How Green Is your Fuel? Creation and Comparison of Automotive Biofuels

Eugene P. Wagner*, Maura A. Koehle, Todd M. Moyle and Patrick D. Lambert
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260
*ewagner@pitt.edu

 J. Chem. Educ., 2010, 87 (7), pp 711–713
DOI: 10.1021/ed100390s
Publication Date (Web): May 13, 2010

 Abstract
In recent years, biofuel development and use has risen significantly. This undergraduate laboratory experiment educates students on the various alternative fuels that are being developed for automotive applications and the advantages and disadvantages of each. Students replicate commercially available alternative fuels, E85 and biodiesel, as well as create an experimental fuel blend of waste vegetable oil and petroleum products referred to as “VeggieDiesel”. Each fuel is evaluated in the lab for energy content and viscosity. Students use laboratory information as well as literature to assess the production energy requirements and environmental impact for each fuel. In addition, students theoretically model heat of combustion and viscosity and compare the predicted values to the experimental results. On the basis of laboratory results and literature findings, students draw conclusions on which fuel they believe is the best “alternative” and most sustainable. The experiment is easily adaptable for organic, analytical, and physical chemistry laboratory courses by inclusion or exclusion of the various tasks and topics covered. Its timely relevance is of interest to anyone interested in environmental chemistry or engineering.

 Keywords:
Second-Year Undergraduate; Upper-Division Undergraduate
Environmental Chemistry; Interdisciplinary/Multidisciplinary; Laboratory Instruction; Organic Chemistry; Physical Chemistry
Hands-On Learning/Manipulatives
Calorimetry/Thermochemistry; Green Chemistry; Physical Properties; Synthesis; Thermodynamics

 

A Green, Enantioselective Synthesis of Warfarin for the Undergraduate Organic Laboratory

Terence C. Wong, Camille M. Sultana and David A. Vosburg*
Department of Chemistry, Harvey Mudd College, Claremont, California 91711
*david_vosburg@hmc.edu

 J. Chem. Educ., 2010, 87 (2), pp 194–195
DOI: 10.1021/ed800040m
Publication Date (Web): January 12, 2010

 Abstract
The enantioselective synthesis of drugs is of fundamental importance in the pharmaceutical industry. In this experiment, students synthesize either enantiomer of warfarin, a widely used anticoagulant, in a single step from inexpensive starting materials. Stereoselectivity is induced by a commercial organocatalyst, (R,R)- or (S,S)-1,2-diphenylethylenediamine. The environmentally friendly microscale reaction is performed at ambient temperature, and the product can be purified by recrystallization or column chromatography. Product characterization includes thin-layer chromatography, NMR spectroscopy, and polarimetry.

 Keywords:
Second-Year Undergraduate; Upper-Division Undergraduate
Organic Chemistry; Laboratory Instruction
Hands-on Learning/Manipulatives
Drugs/Pharmaceuticals; Asymmetric Synthesis; Chirality/Optical Activity; Mechanisms of Reactions; Addition Reactions; Amines/Ammonium Compounds; Green Chemistry; Microscale Lab

 

Nature: "Green" Chemistry, Natural Antioxidants, and a DNA-Fueled Machine

Sabine Heinhorst and Gordon Cannon
Department of Chemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406-5043

 J. Chem. Educ., 2001, 78 (2), p 150
DOI: 10.1021/ed078p150
Publication Date (Web): February 1, 2001

 Abstract
This report from Nature summarizes two breakthroughs in "green" chemistry: A rechargeable Mg battery that might one day become an environmentally benign replacement for our current car batteries, and new polymers that greatly improve the solvent properties of supercritical CO2. Another article highlighted in this column confirms that fresh apples contain oxygen radical scavengers that are more potent than pure vitamin C. Finally, DNA-fueled molecular tweezers are featured that take advantage of the specific interactions between complementary strands of DNA to bring about opening and closing of this nano-device.

 Keywords:
General Public
Polymer Chemistry
Electrochemistry

 

Aqueous-Phase Palladium-Catalyzed Coupling. A Green Chemistry Laboratory Experiment

Brandy A. Harper , J. Chance Rainwater , Kurt Birdwhistell and D. Andrew Knight
Department of Chemistry, Loyola University, New Orleans, LA 70118

 J. Chem. Educ., 2002, 79 (6), p 729
DOI: 10.1021/ed079p729
Publication Date (Web): June 1, 2002

 Abstract
An upper-level inorganic/organic experiment presents important concepts in modern green chemistry. A water-soluble modified triphenylphosphine ligand is prepared and used to prepare a water-soluble palladium catalyst. The palladium catalyst is formed in situ and used for the aqueous, homogenous, palladium-catalyzed cross-coupling reaction of iodobenzene and diethyl phosphite. The product is diethyl phenylphosphonate.

 Keywords:
Upper-Division Undergraduate
Environmental Chemistry
Hands-On Learning / Manipulatives
Catalysis

 

Green Plastics: An Introduction to the New Science of Biodegradable Plastics

Cheryl Baldwin Frech
Department of Chemistry, University of Central Oklahoma, Edmond, OK 73034-5209

 J. Chem. Educ., 2002, 79 (9), p 1072
DOI: 10.1021/ed079p1072.1
Publication Date (Web): September 1, 2002

 Abstract
Environmental chemistry with focus on bioplastics.

 Keywords:
General Public
Environmental Chemistry
Book and Media Reviews
Textbooks / Reference Books
Green Chemistry

 

The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene

Lallie C. McKenzie , Lauren M. Huffman and James E. Hutchison
Department of Chemistry and Materials Science Institute, Universty of Oregon, Eugene, OR 97403-1253

 J. Chem. Educ., 2005, 82 (2), p 306
DOI: 10.1021/ed082p306
Publication Date (Web): February 1, 2005

 Abstract
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield. The use of these metrics to guide experiment evaluation and optimization p style="text-align: justify"in the teaching lab environment is examined. The development of these new experiments provides (i) an ideal case study for demonstrating the process of on-going evaluation and modification of experiments that leads toward more environmentally benign educational materials for the undergraduate organic teaching laboratory and (ii) a concrete example useful for introducing the practical use of metrics to students as a part of their laboratory experience. A green debromination procedure is also described that allows for simple and economical recycling of the starting material.

 Keywords:
Second-Year Undergraduate
Curriculum
Green Chemistry
Hands-On Learning / Manipulatives
Synthesis

 

A Green Starting Material for Electrophilic Aromatic Substitution for the Undergraduate Organic Laboratory

Elizabeth A. Burtch
Cleveland, OH 44111

T. Michelle Jones-Wilson
Department of Chemistry, East Stroudsburg University of Pennsylvania, East Stroudsburg, PA 18301

 J. Chem. Educ., 2005, 82 (4), p 616
DOI: 10.1021/ed082p616
Publication Date (Web): April 1, 2005

 Abstract
Traditional experiments in the undergraduate organic chemistry laboratory involve the use of hazardous organic materials. Substitution of alternative green procedures wherever possible reduces organic waste and allows students to consider the need for environmentally sound chemistry. A green electrophilic aromatic substitution reaction (EAS), nitration of tyrosine, has been developed for use in the undergraduate laboratory. This reaction allows students to consider the varied aspects of EAS including activating and deactivating groups and o, p, m directors in a green environment. Product characterization can be accomplished by melting point, UV, or NMR.

 Keywords:
Upper-Division Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Amino Acids

 

Going Green: Lecture Assignments and Lab Experiences for the College Curriculum

Irvin J. Levy
Department of Chemistry, Gordon College, Wenham, MA 01984

Julie A. Haack
Department of Chemistry, University of Oregon, Eugene, OR 97403

James E. Hutchison
Materials Science Institute, University of Oregon, Eugene, OR 97403

Mary M. Kirchhoff
Education Division, American Chemical Society, Washington, DC 20036

 J. Chem. Educ., 2005, 82 (7), p 974
DOI: 10.1021/ed082p974
Publication Date (Web): July 1, 2005

 Abstract
This paper provides an overview of green chemistry, including ways to incorporate green chemistry principles in existing courses and laboratories. Green chemistry experiments previously published in this Journal are listed.

 Keywords:
First-Year Undergraduate / General
Laboratory Instruction
Association Report: ACS Education
Green Chemistry

 

Teaching Lab Report Writing through Inquiry: A Green Chemistry Stoichiometry Experiment for General Chemistry

Kristen L. Cacciatore
Dedham High School, Dedham, MA 02026

Hannah Sevian
Departments of Chemistry and Curriculum & Instruction, University of Massachusetts Boston, Boston, MA 02125

 J. Chem. Educ., 2006, 83 (7), p 1039
DOI: 10.1021/ed083p1039
Publication Date (Web): July 1, 2006

 Abstract
We present an alternative to a traditional first-year chemistry laboratory experiment. This experiment has four key features: students utilize stoichiometry, learn and apply principles of green chemistry, engage in authentic scientific inquiry, and discover why each part of a scientific lab report is necessary. The importance and essential qualities of written and verbal communication between scientists are discovered by students as they experiment by attempting to replicate different sample lab reports, each lacking some essential information. Experimenting in this way meets several general chemistry goals simultaneously: completion of an experiment on mass–mole relationships in a chemical reaction, demonstration of green chemistry ideas in action, and, most importantly, instruction on how and why scientists communicate in a standard written format. In fact, students invent these standards themselves as they discover this critical process skill through inquiry.

 Keywords:
First-Year Undergraduate / General
Environmental Chemistry
Green Chemistry
Communication / Writing
Quantitative Analysis

 

Connecting Solubility, Equilibrium, and Periodicity in a Green, Inquiry Experiment for the General Chemistry Laboratory

Kristen L. Cacciatore , Jose Amado and Jason J. Evans
Department of Chemistry, University of Massachusetts Boston, Boston, MA 02125

Hannah Sevian
Departments of Chemistry, and Curriculum and Instruction, University of Massachusetts Boston, Boston, MA 02125

 J. Chem. Educ., 2008, 85 (2), p 251
DOI: 10.1021/ed085p251
Publication Date (Web): February 1, 2008

 Abstract
We present a novel first-year chemistry laboratory experiment that connects solubility, equilibrium, and chemical periodicity concepts. It employs a unique format that asks students to replicate experiments described in different sample lab reports, each lacking some essential information, rather than follow a scripted procedure. This structure is designed, based on research findings on the science of learning, to promote development of students' experimental design and data analysis skills as well as their understanding of the importance and essential qualities of written and verbal communication between scientists. The experiment begins with titration of saturated solutions of magnesium, calcium, and strontium hydroxides followed by the calculation of the solubility product of each compound. Students use their results to determine a periodic trend in the solubility of the group 2 compounds they titrated, apply the trend to predict the solubility of other, toxic group 2 hydroxides, and examine the value of the experiment within the context of a green chemistry philosophy.

 Keywords:
First-Year Undergraduate / General
Laboratory Instruction
Hands-On Learning / Manipulatives
Equilibrium

 

Micelle-Mediated Extraction of Heavy Metals from Environmental Samples: An Environmental Green Chemistry Laboratory Experiment

Dimosthenis L. Giokas , Evangelos K. Paleologos and Miltiades I. Karayannis
Department of Chemistry, Laboratory of Analytical Chemistry, University of Ioannina, Ioannina 45110, Greece

 J. Chem. Educ., 2003, 80 (1), p 61
DOI: 10.1021/ed080p61
Publication Date (Web): January 1, 2003

 Abstract
A new laboratory experiment in which students extract and analyze several metallic contaminants from environmental samples is presented. The experimental procedure employs extraction of the target analytes by using an environmentally-benign preconcentrating technique prior to the identifications, which are carried out with a flame atomic absorption spectrometer. The extraction procedure employs complexation of the metallic species via a chelating agent, entrapment and solubilization via micelle formation, and isolation via phase separation when the solution temperature is raised. The overall process involves preparation of standard solutions and construction of a calibration curve, analysis of water samples, and evaluation of the matrix effect, through the analysis of several spiked samples. As a part of the evaluation protocol, a reference sample is also analyzed. Students become familiar with basic principles of analytical, environmental, and green chemistry through a "real world" application.

 Keywords:
First-Year Undergraduate / General
Analytical Chemistry
Problem Solving / Decision Making
Atomic Spectroscopy

 

Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid

Scott M. Reed and James E. Hutchison
Department of Chemistry, Universty of Oregon, Eugene, OR 97403-1253

 J. Chem. Educ., 2000, 77 (12), p 1627
DOI: 10.1021/ed077p1627
Publication Date (Web): December 1, 2000

 Abstract
Environmentally benign ("green") chemical techniques are growing in importance in academic and industrial research laboratories. Such chemistry has been slow to appear in teaching laboratories, owing in part to a lack of published material on this subject. Recent developments in green synthesis provide opportunities to introduce this material in teaching laboratories. We present a synthesis of adipic acid that utilizes green reagents (hydrogen peroxide as the oxidant), solvents (water), and methods (phase-transfer catalysis, catalyst recycling). The synthesis works well and provides an excellent forum for emphasizing green chemical concepts while teaching laboratory skills. It demonstrates reuse of a product, synthesis using a nonhazardous solvent, elimination of deleterious by-products, and use of a recyclable catalyst. It can be carried out on either the macroscale or microscale and generates little waste if the catalyst solution is recycled. This experiment fits well in a sophomore organic sequence; it covers the topics of oxidation, phase-transfer catalysis, and the technique of recrystallization, reinforces lecture topics such as alkene synthesis and reactivity, and provides an opportunity to introduce polymer chemistry.

 Keywords:
Organic Chemistry
Catalysis

 

pH-Controlled Oxidation of an Aromatic Ketone: Structural Elucidation of the Products of Two Green Chemical Reactions

C. Eric Ballard
Department of Chemistry and Physics, University of Tampa, Tampa, Florida 33606-1490

 J. Chem. Educ., 2010, 87 (2), pp 190–193
DOI: 10.1021/ed800054s
Publication Date (Web): January 12, 2010

 Abstract
A laboratory experiment emphasizing the structural elucidation of organic compounds has been developed as a discovery exercise. The “unknown” compounds are the products of the pH-controlled oxidation of 4′-methoxyacetophenone with bleach. The chemoselectivity of this reaction is highly dependent on the pH of the reaction media: under basic conditions, the haloform reaction cleaves the methyl ketone yielding 4-methoxybenzoic acid, but under acidic conditions, electrophilic aromatic substitution of the aromatic ring occurs to generate 3′-chloro-4′-methoxyacetophenone. Each product was characterized by physical methods including melting point determination, IR and proton and carbon NMR spectroscopies, and mass spectrometry. Students analyzed the experimental data to determine the structures of the products. The experiment allows for an introduction of the concepts of chemoselectivity and regioselectivity and a discussion of redox reactions in organic chemistry. In addition, since the reactions were conducted using a relatively mild oxidant and with little organic solvent, principles of green chemistry and sustainable development are demonstrated.

 Keywords:
Second-Year Undergraduate; Upper-Division Undergraduate
Laboratory Instruction; Organic Chemistry
Hands-On Learning/Manipulatives; Inquiry-Based/Discovery Learning
Aldehydes/Ketones; Aromatic Compounds; Electrophilic Substitution; Green Chemistry; IR Spectroscopy; Mass Spectrometry; NMR Spectroscopy; Oxidation/Reduction

 

Green Chemistry Laboratory: Benign Synthesis of 4,6-Diphenyl[2,2']bipyridine via Sequential Solventless Aldol and Michael Addition Reactions

Colin L. Raston
School of Biomedical and Chemical Sciences, University of Western Australia, Crawley WA 6009, Australia

Gareth W. V. Cave
School of Biomedical and Natural Sciences, Nottingham Trent University, Nottingham, NG11 8NS, United Kingdom

 J. Chem. Educ., 2005, 82 (3), p 468
DOI: 10.1021/ed082p468
Publication Date (Web): March 1, 2005

 Abstract
Solventless reaction methodology avoids the use of hazardous and toxic solvents and minimizes generation of waste, thereby addressing some of the principles of green chemistry. 2,4,6-Trisubstituted pyridines are readily prepared in high yield using this methodology in three steps: (i) solventless aldol condensation of benzaldehyde and acetophenone, (ii) solventless Michael addition of 2-acetylpyridine to the previously formed 1,3-diphenylpropenone, and (iii) the ring closure of the resulting 1,5-diketone in acetic acid with ammonium acetate. An undergraduate laboratory has been developed teaching the relevant principles of green chemistry, at the same time teaching traditional aspects of organic synthesis. The laboratory incorporates critical questions and demonstrates the advantages of the paradigm shift in using solventless reaction methodology compared to traditional approaches using organic solvents, as well as drawing attention to applications in other areas of chemistry including medicinal and supramolecular materials chemistry. The laboratory is inherently simpler and quicker, requiring less time and demand on equipment. All products and intermediates can be unambiguously characterized by NMR (1H and 13C) and IR spectrographic techniques.

 Keywords:
Upper-Division Undergraduate
Environmental Chemistry
Green Chemistry
Hands-On Learning / Manipulatives

 

Synthesis of meso-Diethyl-2,2'-dipyrromethane in Water. An Experiment in Green Organic Chemistry

Abilio J. F. N. Sobral
Department of Chemistry, University of Coimbra, Coimbra, Portugal

 J. Chem. Educ., 2006, 83 (11), p 1665
DOI: 10.1021/ed083p1665
Publication Date (Web): November 1, 2006

 Abstract
In this laboratory activity, students are introduced to the synthesis of dipyrromethanes, which are important precursors for porphyrin and calix[4]pyrrole. The acid-catalyzed condensation of pyrrole and 3-pentanone in water uses common inexpensive reagents and solvents to produce the meso-diethyl-2,2′-dipyrromethane in one step, in an analytical grade directly from the aqueous reaction medium.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone by Sodium Borohydride and Baker's Yeast

Nicola Pohl , Allen Clague and Kimberly Schwarz
Department of Chemistry, Iowa State University, Ames, IA 50011-3111

 J. Chem. Educ., 2002, 79 (6), p 727
DOI: 10.1021/ed079p727
Publication Date (Web): June 1, 2002

 Abstract
We describe an integrated set of experiments for the undergraduate organic laboratory that allows students to compare and contrast biological and chemical means of introducing chirality into a molecule. The racemic reduction of ethyl acetoacetate with sodium borohydride and the same reduction in the presence of a tartaric acid ligand are described, and a capillary gas chromatography column packed with a chiral material for product analysis is introduced. The results of these two hydride reactions are compared with the results of a common undergraduate experiment, the baker's yeast reduction of ethyl acetoacetate.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Hands-On Learning / Manipulatives
Chirality / Optical Activity

 

Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay. Green Chemistry in the Undergraduate Organic Laboratory

Matthew R. Dintzner , Paul R. Wucka and Thomas W. Lyons
Department of Chemistry, DePaul University, Chicago, IL 60614

 J. Chem. Educ., 2006, 83 (2), p 270
DOI: 10.1021/ed083p270
Publication Date (Web): February 1, 2006

 Abstract
A microwave-assisted, one-pot synthesis of a naturally occurring insecticide on basic Montmorillonite K10 is described. The reaction is suitable for incorporation into the undergraduate organic chemistry laboratory course and represents a practical example of green chemistry. The described synthesis employs naturally benign, base-washed Montmorillonite K10 clay as a heterogeneous catalyst, is carried out under solvent-free conditions in a commercial-grade microwave oven, and features several interesting mechanistic considerations, including an electrophilic aromatic addition, dehydration, and intramolecular hetero-Diels–Alder cyclization.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Chromatography

 

Mannich Reactions in Room Temperature Ionic Liquids (RTILs): An Advanced Undergraduate Project of Green Chemistry and Structural Elucidation

Kendrew K. W. Mak , Jane Siu , Y. M. Lai and Pak-kei Chan
Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong SAR, PRC

 J. Chem. Educ., 2006, 83 (6), p 943
DOI: 10.1021/ed083p943
Publication Date (Web): June 1, 2006

 Abstract
This is a mini laboratory project on green chemistry suitable for junior-level students. The objective of this experiment is to allow students to gain exposure to the innovative ideas of current chemistry research and experience research-oriented work as in postgraduate studies. Recent research has shown that room temperature ionic liquids (RTILs) are promising replacements for traditional volatile organic solvents for organic reactions. RTILs, being ionic compounds, have the advantages of low volatility, good chemical and thermal stabilities, good activity for a variety of organic reactions, and are readily recyclable so that chemical waste disposal can be minimized. This experiment describes the synthesis of a commonly used ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF4], and the application of this ionic liquid as a recyclable medium for Mannich reactions. Benzaldehyde, 3-pentanone, and ammonium acetate undergo a stereospecific double Mannich reaction when mixed in the ratio of 2:1:1 in [bmim][BF4] and give a tetrasubstituted piperidone as the product. Students are required to identify the chemical structure and the stereochemistry of the product by examining the mechanism of the reaction and the spectroscopic data.

 Keywords:
Upper-Division Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

On the Use of "Green" Metrics in the Undergraduate Organic Chemistry Lecture and Lab To Assess the Mass Efficiency of Organic Reactions

John Andraos and Murtuzaali Sayed
Department of Chemistry, York University, Toronto, ON M3J 1P3, Canada

 

J. Chem. Educ., 2007, 84 (6), p 1004
DOI: 10.1021/ed084p1004
Publication Date (Web): June 1, 2007

 Abstract
This article describes a novel approach to evaluate the complete reaction mass efficiency (RME) and raw material cost (RMC) of any chemical transformation through the implementation of an Excel spreadsheet in a tax-form style and an easy graphical representation of the results. The complete equation for evaluating RME is presented. Students and their lab instructors will be able to see at once the material performance of their laboratory reaction and evaluate critically which of the four parameters (reaction yield, atom economy, stoichiometric factor, and material recovery parameter) needs further optimization to bring about a “greener” synthesis plan. The effect of material recovery options on RME and RMC are also given. The methodology is applied to a wide variety of organic reaction types and key trends in the material efficiency performances are summarized.

 Keywords:
Graduate Education / Research
Organic Chemistry
Green Chemistry
Computer-Based Learning

 

Synthesis of Imidazolium Room-Temperature Ionic Liquids. Exploring Green Chemistry and Click Chemistry Paradigms in Undergraduate Organic Chemistry Laboratory

Sergei V. Dzyuba , Katherine D. Kollar and Salil S. Sabnis
Department of Chemistry, Texas Christian University, Fort Worth, TX 76129

 J. Chem. Educ., 2009, 86 (7), p 856
DOI: 10.1021/ed086p856
Publication Date (Web): July 1, 2009

 Abstract
Room-temperature ionic liquids have become a widely used alternative to conventional molecular organic solvents as a reaction medium. Few preparations of ionic liquids provide efficient access to these solvents; furthermore, none is fully adaptable to an undergraduate organic chemistry laboratory. In this article, several imidazolium-based ionic liquids are formed in facile and efficient one-pot procedures using water or ethanol as a solvent. These reactions are suited for a four-hour organic chemistry laboratory without special equipment.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Alkylation

 

Microscale Syntheses, Reactions, and 1H NMR Spectroscopic Investigations of Square Planar Macrolyclic Tetraamido-N Co(III) Complexes Relevant to Green Chemistry

Erich S. Uffelman , Jonathan R. Doherty , Carl Schulze , Amy L. Burke , Kristen R. Bonnema , Tanya T. Watson and Daniel W. Lee III
Department of Chemistry, Washington and Lee University, Lexington, VA 24450

 J. Chem. Educ., 2004, 81 (3), p 325
DOI: 10.1021/ed081p325
Publication Date (Web): March 1, 2004

 Abstract
We describe a two- to three-week experiment for junior and senior chemistry majors that involves the microscale preparation, characterization, and reactivity of a square planar macrocyclic tetraamide Co(III) complex relevant to green chemistry. The characterization process includes significant use of 1H NMR spectroscopy, along with the optional use of FT–IR and UV–vis spectroscopies. These labs and accompanying lab lectures and discussions create a problem-based learning environment that involves Brønsted acid–base chemistry, steric arguments, redox processes, Le Châtelier's principle, nonaqueous chemistry, solubility product constants, periodic trends, organic reactivity, and spectroscopy.

 Keywords:
Upper-Division Undergraduate
Inorganic Chemistry
NSF Highlights
Problem Solving / Decision Making
Coordination Compounds

 

Microscale Syntheses, Reactions, and 1H NMR Spectroscopic Investigations of Square Planar Macrocyclic Tetraamido-N Cu(III) Complexes Relevant to Green Chemistry

Erich S. Uffelman , Jonathan R. Doherty , Carl Schultze , Amy L. Burke , Kristen R. Bonnema , Tanya T. Watson and Daniel W. Lee III
Department of Chemistry, Washington and Lee University, Lexington, VA 24450

 J. Chem. Educ., 2004, 81 (2), p 182
DOI: 10.1021/ed081p182
Publication Date (Web): February 1, 2004

 Abstract
We describe a two- or three-week experiment for junior and senior chemistry majors that involves the microscale preparation, characterization, and reactivity of a square planar macrocyclic tetraamide Cu(III) complex relevant to green chemistry. The characterization process includes significant use of 1H NMR spectroscopy, along with the optional use of FT–IR and UV–vis spectroscopies. These labs and accompanying lab lectures and discussions create a problem-based learning environment that involves Brønsted acid–base chemistry, steric arguments, redox processes, Le Châtelier's principle, nonaqueous chemistry, solubility product constants, periodic trends, organic reactivity, and spectroscopy.

 Keywords:
Upper-Division Undergraduate
Inorganic Chemistry
NSF Highlights
Problem Solving / Decision Making
Coordination Compounds

 

Infusing the Chemistry Curriculum with Green Chemistry Using Real-World Examples, Web Modules, and Atom Economy in Organic Chemistry Courses

Michael C. Cann and Trudy A. Dickneider
Department of Chemistry, University of Scranton, Scranton, PA 18510

 J. Chem. Educ., 2004, 81 (7), p 977
DOI: 10.1021/ed081p977
Publication Date (Web): July 1, 2004

 Abstract
Green chemistry principles and practices have been infused in the chemistry curriculum at the University of Scranton, including courses in general, organic, and inorganic chemistry, biochemistry, environmental, polymer, industrial, and advanced organic chemistry, and chemical toxicology. Web-based green chemistry teaching modules have been developed for each of these courses. We describe the principles underlying green chemistry and methods of introducing these concepts into the curriculum with an example of incorporating green chemistry into the undergraduate lecture and laboratory organic sequence.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry
Internet / Web-Based Learning

 

An Inexpensive, Relatively Green, and Rapid Method To Purify Genomic DNA from Escherichia coli: An Experiment for the Undergraduate Biochemistry Laboratory

Paul A. Sims*, Katie M. Branscum, and Lydia Kao
Department of Chemistry and Biochemistry, University of Oklahoma, Norman, Oklahoma 73019
*psims@ou.edu

Virginia R. Keaveny
Department of Chemistry, Minot State University, Minot, North Dakota 58707

 J. Chem. Educ., 2010, 87 (10), pp 1113–1115
DOI: 10.1021/ed100237e
Publication Date (Web): July 30, 2010

 Abstract
A method to purify genomic DNA from Escherichia coli is presented. The method is an amalgam of published methods but has been modified and optimized for use in the undergraduate biochemistry laboratory. Specifically, the method uses Tide Free 2× Ultra laundry detergent, which contains unspecified proteases and lipases, n-butanol, 2-propanol, ethanol, and ribonuclease A (or 8 mM sodium hydroxide), and requires a minimum of specialty equipment. Because a number of the required reagents are readily attainable from retail stores, the cost is low enough to allow each student to prepare a sample of purified genomic DNA, even in large laboratory classes. By following the protocol, students are able to purify genomic DNA and use this genomic DNA as a template for a polymerase chain reaction in one 3-h laboratory period.

 Keywords:
Upper-Division Undergraduate
Biochemistry; Laboratory Instruction
Hands-On Learning/Manipulatives
Green Chemistry; Nucleic Acids/DNA/RNA

 

The Question-Driven Laboratory Exercise: A New Pedagogy Applied to a Green Modification of Grignard Reagent Formation and Reaction

Jennifer M. Teixeira, Jessie Nedrow Byers, Marilu G. Perez and R. W. Holman*
Department of Chemistry, Idaho State University, Pocatello, Idaho 83209-8023
*holmrobe@isu.edu

 J. Chem. Educ., 2010, 87 (7), pp 714–716
DOI: 10.1021/ed1002866
Publication Date (Web): May 13, 2010

 Abstract
Experimental exercises within second-year-level organic laboratory manuals typically involve a statement of a principle that is then validated by student generation of data in a single experiment. These experiments are structured in the exact opposite order of the scientific method, in which data interpretation, typically from multiple related experiments, leads to the development of a principle. The question-driven laboratory exercise (QDLE) better mimics a research investigative process in that data from multiple experiments provided to students are coupled with student-generated data with the goal being the development of a principle. To facilitate students’ ability to tether together interpretations from multiple experiments, the entire exercise is driven by guiding questions. This general approach is applicable to a broad array of potential laboratory exercises. In this example, students are guided to develop a more environmentally friendly solvent system for Grignard formation and reaction, test the new system via a laboratory experiment, and then discern between two competing proposed mechanisms for describing Grignard reagent formation in the modified media. To accomplish this goal, the students will be guided to interpret and synthesize data (some provided, some student generated) from 13C NMR, GC−MS, and computational investigations.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction; Organic Chemistry
Computational Chemistry; Green Chemistry; Grignard Reagents; Mechanisms of Reactions

 

Green, Enzymatic Syntheses of Divanillin and Diapocynin for the Organic, Biochemistry, or Advanced General Chemistry Laboratory

Rachel T. Nishimura, Chiara H. Giammanco and David A. Vosburg*
Department of Chemistry, Harvey Mudd College, Claremont, California 91711
*vosburg@hmc.edu

 J. Chem. Educ., 2010, 87 (5), pp 526–527
DOI: 10.1021/ed8001607
Publication Date (Web): March 10, 2010

 Abstract
Environmentally benign chemistry is an increasingly important topic both in the classroom and the laboratory. In this experiment, students synthesize divanillin from vanillin or diapocynin from apocynin, using horseradish peroxidase and hydrogen peroxide in water. The dimerized products form rapidly at ambient temperature and are isolated by filtration. The products are readily distinguished from starting materials by solubility, NMR spectroscopy, or melting point analysis. The experiment is adaptable to an organic chemistry course in the context of radical reactions of phenols, to a biochemistry course in the context of metalloenzymes, or to an advanced general chemistry course in the context of green chemistry.

 Keywords:
First-Year Undergraduate/General; Second-Year Undergraduate; Upper-Division Undergraduate
Biochemistry; Inorganic Chemistry; Laboratory Instruction; Organic Chemistry; Physical Chemistry
Hands-On Learning/Manipulatives
Enzymes; Green Chemistry; Mechanisms of Reactions; Natural Products; NMR Spectroscopy; Oxidation/Reduction; Precipitation/Solubility; Synthesis

 

The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal Triflates. A Microscale Green Organic Chemistry Laboratory Experiment

James E. Christensen , Matthew G. Huddle , Jamie L. Rogers , Herbie Yung and Ram S. Mohan
Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61701

 J. Chem. Educ., 2008, 85 (9), p 1274
DOI: 10.1021/ed085p1274
Publication Date (Web): September 1, 2008

 Abstract
Although green chemistry principles are increasingly stressed in the undergraduate curriculum, there are only a few lab experiments wherein the toxicity of reagents is taken into consideration in the design of the experiment. We report a microscale green organic chemistry laboratory experiment that illustrates the utility of metal triflates, especially bismuth triflate as a Lewis acid catalyst. Bismuth compounds are especially attractive for use as catalysts in organic synthesis because of their remarkably low toxicity, low cost, and ease of handling.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Catalysis

 

A Microscale Heck Reaction In Water

Lawrence L. W. Cheung, Evangelos Aktoudianakis, Elton Chan, Amanda R. Edward, Isabel Jarosz, Vicki Lee, Leo Mui, Sonya S. Thatipamala and Andrew P. Dicks*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6, adicks@chem.utoronto.ca

 The Chemical Educator
Abstract Volume 12 Issue 2 (2007) pp 77-79
DOI 10.1333/s00897072011a

 Abstract
This paper describes the Heck synthesis of (E)-4-acetylcinnamic acid from 4-iodoacetophenone and acrylic acid under catalysis by Pd (0). Traditional Heck reaction organic solvents (acetonitrile, N-methyl-2-pyrrolidone) and base (triethylamine) are replaced by water and sodium carbonate respectively. This approach introduces fundamentals of green chemistry to undergraduates whilst highlighting current research via an industrially significant reaction.

 Key Words:
Laboratories and Demonstrations
organic chemistry
microscale synthesis
aqueous reactivity
heck reaction
palladium catalysis

 

Oxidation of Aromatic Aldehydes Using Oxone

Rajani Gandhari , Padma P. Maddukuri and Thottumkara K. Vinod
Department of Chemistry, Western Illinois University, Macomb, IL 61455

 J. Chem. Educ., 2007, 84 (5), p 852
DOI: 10.1021/ed084p852
Publication Date (Web): May 1, 2007

 Abstract
An eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant is described. An easy isolation of the precipitated product upon cooling the reaction mixture helps avoid the use of extraction solvents in the product isolation procedure. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to the students. The optimized experimental procedure reported herein allows students to successfully carry out the experiment, isolate the product, and characterize the purified product through melting point determination and 1H NMR spectroscopy during a three-hour laboratory period.

 Keywords:
Second-Year Undergraduate
Environmental Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

Expeditious Horner-Wadsworth–Emmons Synthesis of Methyl Cinnamate Esters under Aqueous Conditions

Lawrence L. W. Cheung, Rui Jun Lin, Jason W. McIntee, and Andrew P. Dicks*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6, adicks@chem.utoronto.ca

 The Chemical Educator
Abstract Volume 10 Issue 4 (2005) pp 300-302
DOI 10.1333/s00897050933a

 Abstract
The rapid and facile preparation of methyl (E)-cinnamate esters by a Horner–Wadsworth–Emmons reaction is detailed. Reactions are undertaken using environmentally benign potassium carbonate as a base in an aqueous medium. This methodology introduces a significant reduction in reaction time compared to previous undergraduate experiments. An occasion exists to promote recognition of the role water plays as a solvent for organic reactions and aspects of green chemistry.

 

Key Words:
Laboratories and Demonstrations
organic chemistry
microscale synthesis
aqueous reactivity
Horner–Wadsworth–Emmons reaction
methyl cinnamate esters

 

"Greening Up" the Suzuki Reaction

Evangelos Aktoudianakis , Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. Dicks
Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada

 J. Chem. Educ., 2008, 85 (4), p 555
DOI: 10.1021/ed085p555
Publication Date (Web): April 1, 2008

 Abstract
This article describes the rapid, green synthesis of a biaryl compound (4-phenylphenol) via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water. Mild reaction conditions and operational simplicity makes this experiment especially amenable to both mid- and upper-level undergraduates. The methodology exposes students to purely aqueous microscale organic reactivity and showcases topical research in the milieu of an industrially applicable process.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Aromatic Compounds

 

Determination of the Formula of a Hydrate: A Greener Alternative

Marc A. Klingshirn , Allison F. Wyatt , Robert M. Hanson and Gary O. Spessard
Department of Chemistry, St. Olaf College, Northfield, MN 55057

 J. Chem. Educ., 2008, 85 (6), p 819
DOI: 10.1021/ed085p819
Publication Date (Web): June 1, 2008

 Abstract
We are currently in the process of incorporating green chemistry throughout the chemistry curriculum. In this article we describe how we applied the principles of green chemistry in one of our first-semester general chemistry courses, specifically in relation to the determination of the formula of a hydrate. We utilize a copper hydrate salt that shows both a visual color change upon dehydration and ease of rehydration upon exposure to steam.

 Keywords:
First-Year Undergraduate / General
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Gravimetric Analysis

 

Developing and Disseminating NOP: An Online, Open-Access, Organic Chemistry Tea/pching Resource To Integrate Sustainability Concepts in the Laboratory

Marco Eissen
D-27777 Ganderkesee, Germany

Müfit Bahadir
Institute of Ecological Chemistry and Waste Analysis, Braunschweig University of Technology, D-38106 Braunschweig, Germany

Burkhard König
Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany

Johannes Ranke
UFT—Center for Environmental Research and Technology, University of Bremen, D-28334 Bremen, Germany

 J. Chem. Educ., 2008, 85 (7), p 1000
DOI: 10.1021/ed085p1000
Publication Date (Web): July 1, 2008

 Abstract
To foster greater awareness of sustainability issues in chemistry among future professional chemists, traditional course content must be revised. We have collected and developed material that allows students and teachers of organic chemistry to assess reactions beyond experimental set ups, reaction mechanisms, and chemical yields. The NOP resource we use and distribute freely online includes additional parameters that should be considered in the organic chemistry laboratory: atom economy of chemical transformations; energy efficiency of chemical transformations; questions of waste; renewable feedstocks; toxicity and ecotoxicity; and safety measures for the chemicals used. We report on the development, use, and international adoption of NOP project efforts to promote sustainable practices in organic chemistry laboratories.

 Keywords:
First-Year Undergraduate / General
Organic Chemistry
Green Chemistry
Internet / Web-Based Learning
Green Chemistry

 

Greener Alternative to Qualitative Analysis for Cations without H2S and Other Sulfur-Containing Compounds

Indu Tucker Sidhwani and Sushmita Chowdhury
Department of Chemistry, Gargi College, University of Delhi, Delhi-110049, India

 J. Chem. Educ., 2008, 85 (8), p 1099
DOI: 10.1021/ed085p1099
Publication Date (Web): August 1, 2008

 Abstract
Qualitative analysis of inorganic salts and mixtures is an essential experiment carried out in high school, undergraduate, and postgraduate levels all over the world especially in India and South Asia. The classical technique uses H2S, which is highly toxic and has adverse effects on humans and the environment. Increasing awareness concerning a healthy environment has prompted us to develop a green scheme for detection of cations. NH4+ and K+ are detected directly in group zero. Pb2+ and Ag+ are detected in group I as chlorides using dilute HCl. Ca2+, Sr2+, Ba2+, and Pb2+ are precipitated in group II as sulfates using Na2SO4(aq) and ethanol. Cu2+, Cd2+, Fe3+, Mn2+, Co2+, Ni2+, and Mg2+ are precipitated as hydroxides using NaOH and H2O2 in group III. The precipitate is treated with NH3(aq) leaving a residue (group IIIA: Fe3+, Mn2+, Mg2+ as hydroxides) and the centrifugate (group IIIB: Cu2+, Cd2+, Ni2+, Co2+ as soluble ammines). Al3+, Zn2+, Sn2+/Sn4+ (as soluble hydroxo complexes), and Cr3+ (as CrO42-) are detected in group IV, in the presence of each other by using selective reagents. The separation is sharp; individual cations are detected by spot tests and conventional methods. This scheme is simple and fast and makes green chemistry accessible to students.

 Keywords:
First-Year Undergraduate / General
Analytical Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Green Chemistry

 

The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction. An Undergraduate Project in Organic Synthesis and Structural Analysis

Xavier Sauvage and Lionel Delaude
Département de Chimie, Institut de Chimie, Université de Liège, Sart-Tilman, 4000 Liège, Belgium

 J. Chem. Educ., 2008, 85 (11), p 1538
DOI: 10.1021/ed085p1538
Publication Date (Web): November 1, 2008

 Abstract
The synthesis of N-benzyl-2-azanorbornene via aqueous hetero Diels–Alder reaction of cyclopentadiene and benzyliminium chloride formed in situ from benzylamine hydrochloride and formaldehyde is described. Characterization of the product was achieved by IR and NMR spectroscopies. The spectral data acquired are thoroughly discussed. Numerous coupling constants were extracted from the 1H NMR spectrum. They provide a valuable material to familiarize students with the different types of proton–proton coupling patterns and their typical ranges. Karplus type correlations served to calculate 3J vicinal coupling constants as a function of dihedral angles. These computational studies involved molecular modeling. Because the synthetic part is rather straightforward and easy to carry out, this experiment is suitable for an introductory laboratory course where it can serve to illustrate the concepts of green chemistry and atom efficiency. Emphasis can also be placed on structural analysis for use within a spectroscopy course even if there is no activity component associated with it. Last but not least, the whole project provides ample materials for an advanced undergraduate laboratory in green chemistry that combines organic synthesis, structural analysis, and theoretical calculations.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Hands-On Learning / Manipulatives
Alkenes

 

Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl trans-Cinnamate and trans-3- (9-Anthryl)-2-Propenoic Acid Ethyl Ester

Kim Chi Nguyen and Haim Weizman
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0303

 J. Chem. Educ., 2007, 84 (1), p 119
DOI: 10.1021/ed084p119
Publication Date (Web): January 1, 2007

 Abstract
The two reactions presented here are solvent-free alternatives to published procedures of Wittig reactions. The first example is a reaction between a solid phosphorane and liquid aldehyde while the second reaction takes place in a melt. Both reactions are fast, proceed with high yield and excellent stereoselectivity, and their product isolation is simple. The simplicity of the experiments allows students to perform them simultaneously and to construct a small NMR data set. The spectral data provide a basis for an inquiry-based discussion of (i) the factors influencing the chemical shifts of alkenyl proton, (ii) the analysis of NMR spectrum containing a mixture, and (iii) the role of strong dipole–dipole interactions in dictating the stereochemical outcome of the Wittig reaction.

 Keywords:
Upper-Division Undergraduate
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction

Eric Martin and Cynthia Kellen-Yuen
Department of Chemistry , California State University–Sacramento, Sacramento, CA 95819-6057

 J. Chem. Educ., 2007, 84 (12), p 2004
DOI: 10.1021/ed084p2004
Publication Date (Web): December 1, 2007

 Abstract
A greener, microwave-assisted Wittig reaction has been developed for the second-semester organic teaching laboratory. Utilizing this microwave technique, a variety of styrene derivatives have been successfully synthesized from aromatic aldehydes in good yields (41–68%). The reaction not only occurs under neat reaction conditions, but also employs an inexpensive, non-pyrophoric base and readily available glassware. The average reaction times have been reduced to a matter of minutes rather than the hours typical of literature procedures. This method will therefore provide a quick and easy example of a Wittig reaction that can be accomplished in any undergraduate organic lab. The mixture of cis and trans alkenes produced by this method also provides instructors with opportunities to emphasize spectroscopic analysis of product mixtures.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

News from Online: Renewable Resources

Erich S. Uffelman
Department of Chemistry, Washington and Lee University, Lexington, VA 24450

 J. Chem. Educ., 2007, 84 (2), p 220
DOI: 10.1021/ed084p220
Publication Date (Web): February 1, 2007

 Abstract
An introductory, non-exhaustive set of online resources is presented to provide readers with an entry into the area of renewable resources, especially biofuels.

 Keywords:
General Public
Curriculum
Reports from Other Journals
Green Chemistry

 

Toward the Greening of Our Minds: A New Special Topics Course

Anne E. Marteel-Parrish
Department of Chemistry, Washington College, Chestertown, MD 21620

 J. Chem. Educ., 2007, 84 (2), p 245
DOI: 10.1021/ed084p245
Publication Date (Web): February 1, 2007

 Abstract
Nowadays environmentally friendly scientists are conscious about the need to make chemistry "greener". The success of green chemistry depends on the training of the students of today. Facing the need to open students' minds on the greener side of chemistry, a new special-topics course has been developed that covers both the theoretical and practical aspects of green chemistry. The main goal of this course is to motivate the students to use their critical-thinking and problem-solving ability in learning about green chemistry. The originality of this course arises from the unique combination of using diverse pedagogical tools to teach a new chemistry topic as well as the active-learning approach engaging the students in the course material. The course goals, instructional materials, format of the course, grading, evaluation, conclusions of the course are detailed in this article and corresponding Supplemental Material. This outline is designed to provide a model to instructors wishing to integrate a green chemistry course in their curriculum.

 Keywords:
Upper-Division Undergraduate
Environmental Chemistry
Green Chemistry
Collaborative / Cooperative Learning
Green Chemistry

 

Determination of the Heat of Combustion of Biodiesel Using Bomb Calorimetry. A Multidisciplinary Undergraduate Chemistry Experiment

Stephen M. Akers , Jeremy L. Conkle , Stephanie N. Thomas and Keith B. Rider
Department of Natural Sciences, Longwood University, Farmville, VA 23909

 J. Chem. Educ., 2006, 83 (2), p 260
DOI: 10.1021/ed083p260
Publication Date (Web): February 1, 2006

 Abstract
An integrated undergraduate laboratory activity involving the synthesis and characterization of a diesel fuel substitute, biodiesel, is presented. Biodiesel is currently a popular topic in the field of green chemistry because it is a non-petroleum fuel that can be efficiently produced from waste vegetable oil. As a fuel, it requires no engine modifications and results in lower pollution emissions including carcinogens and carbon dioxide. Over a three-week period, students synthesize biodiesel, measure its heat of combustion, density, and cloud point, then compare these properties to conventional petroleum diesel. Heats of combustion are measured in a common laboratory bomb calorimeter and cloud point is measured using a UV–vis spectrophotometer.

 Keywords:
Upper-Division Undergraduate
Environmental Chemistry
Hands-On Learning / Manipulatives
Calorimetry / Thermochemistry

 

Enantioselective Reduction by Crude Plant Parts: Reduction of Benzofuran-2-yl Methyl Ketone with Carrot (Daucus carota) Bits

Silvana Ravía , Daniela Gamenara , Valeria Schapiro , Ana Bellomo , Jorge Adum , Gustavo Seoane and David Gonzalez
Departamento de Química Orgánica, Facultad de Química, General Flores 2124, Montevideo, Uruguay

 J. Chem. Educ., 2006, 83 (7), p 1049
DOI: 10.1021/ed083p1049
Publication Date (Web): July 1, 2006

 Abstract
The use of biocatalysis and biotransformations are important tools in green chemistry. The enantioselective reduction of a ketone by crude plant parts, using carrot (Daucus carota) as the reducing agent is presented. The experiment introduces an example of a green chemistry procedure that can be tailored to fit in a regular laboratory session. Among other concepts, the experiment teaches chromatographic separation on the microscale level.

 Keywords:
First-Year Undergraduate / General
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

Environmentally Responsible Redox Chemistry: An Example of Convenient Oxidation Methodology without Chromium Waste

Robyn L. Crumbie
School of Science, Food and Horticulture, University of Western Sydney, Campbelltown Campus, NSW 1797, Australia

 J. Chem. Educ., 2006, 83 (2), p 268
DOI: 10.1021/ed083p268
Publication Date (Web): February 1, 2006

 Abstract
The need for environmentally friendly manufacturing processes has given rise to significant research into environmentally sensitive chemistry, commonly referred to as "green chemistry". By and large, this has not yet translated into informative undergraduate experiments. This article describes a simple experiment that uses recyclable Magtrieve as the oxidant in a simple reaction sequence emphasizing the reciprocity of oxidation and reduction processes in organic synthesis.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Hands-On Learning / Manipulatives
Chromatography

 

Microwave-Assisted Heterocyclic Chemistry for Undergraduate Organic Laboratory

Robert Musiol , Bozena Tyman-Szram and Jaroslaw Polanski
Department of Organic Chemistry, University of Silesia, Katowice 40-007, Poland

 J. Chem. Educ., 2006, 83 (4), p 632
DOI: 10.1021/ed083p632
Publication Date (Web): April 1, 2006

 Abstract
Heterocyclic chemistry forms an interesting and important part of organic chemistry. Microwave-assisted techniques were applied to design new environmentally benign syntheses of heterocycles for the undergraduate organic laboratory. To avoid toxic solvents, solid-phase synthesis and neat methods were applied. New procedures for the synthesis of seven unique heterocyclic compounds are simple, low cost, safe, and time sparing.

 Keywords:
First-Year Undergraduate / General
Laboratory Instruction
Green Chemistry
Hands-On Learning / Manipulatives
Green Chemistry

 

Reductive Amination: A Remarkable Experiment for the Organic Laboratory

Kim M. Touchette
Bard College, Annandale-on-Hudson, NY 12504

 J. Chem. Educ., 2006, 83 (6), p 929
DOI: 10.1021/ed083p929
Publication Date (Web): June 1, 2006

 Abstract
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory. The first step is a spectacular solvent-free solid-solid reaction between ortho-vanillin and para-toluidine to synthesize an imine in quantitative yield. The imine is reduced to an amine in the second step by sodium borohydride. The amine is acetylated in the third step to form the solid amide in an overall yield of 90%. The entire sequence is performed in an open beaker in less than one hour.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Hands-On Learning / Manipulatives
Aldehydes / Ketones

 

A Greener Approach for Measuring Colligative Properties

Sean M. McCarthy and Scott W. Gordon-Wylie
Department of Chemistry, University of Vermont, Cook Burlington, VT 05405

 J. Chem. Educ., 2005, 82 (1), p 116
DOI: 10.1021/ed082p116
Publication Date (Web): January 1, 2005

 Abstract
As a first step towards the greening of instructional laboratories, we present a new greener version of a laboratory procedure designed to measure colligative properties. The greener procedure substitutes the nontoxic, noncarcinogenic compounds stearic, myristic, lauric, and palmitic acids for the less benign aromatic compounds p-dichlorobenzene, benzil, biphenyl, naphthalene, and nitrotoluene. Achieving educational goals without the concomitant generation of chlorinated and aromatic wastes is shown here to be both possible and practical. Furthermore, utilization of the benign fatty acid waste stream for other purposes, such as making soap, wax, or biodiesel, allows this laboratory to approach the zero waste benchmark.

 Keywords:
High School / Introductory Chemistry
Physical Ch emistry/p
Green Chemistry
Hands-On Learning / Manipulatives
Fatty Acids

 

A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone

John J. Esteb , J. Nathan Hohman , Diana E. Schlamadinger and Anne M. Wilson
Clowes Department of Chemistry, Butler University, Indianapolis, IN 46208

 J. Chem. Educ., 2005, 82 (12), p 1837
DOI: 10.1021/ed082p1837
Publication Date (Web): December 1, 2005

 Abstract
We present an experiment involving the Baeyer–Villiger oxidation reactionfor a first-year organic chemistry class. The Baeyer–Villiger reactionprovides an efficient method to convert ketones to esters or lactones. Most organictextbooks cover the Baeyer–Villiger reaction but owing to a lack of suitableexperiments, students seldom get to explore the reaction in the undergraduateteaching laboratory. In this experiment, m-chloroperoxybenzoic acid(m-CPBA) and4-tert-butylcyclohexanone are mixed together for 30 minutes under solvent-freeconditions to produce γ-t-butyl-ε-caprolactone in 95%yield. The solvent-free nature of this procedure greatly limits the quantityof waste generated by students and keeps costs low by removing the need for solvent.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Hands-On Learning / Manipulatives
Green Chemistry

 

Comparative Methylation of 1,8-Dihydroxy-9,10-anthraquinone: Chemoselectivity in the Organic Chemistry Laboratory

Grigoriy A. Sereda
Department of Chemistry, University of South Dakota, Vermillion, SD 57069

 J. Chem. Educ., 2005, 82 (12), p 1839
DOI: 10.1021/ed082p1839
Publication Date (Web): December 1, 2005

 Abstract
We have developed a laboratory experiment that gives organic chemistry students an example of an environmentally friendly pyrolytic procedure of organic synthesis. Another synthesis with the same reactants teaches the students that appropriate reaction conditions may allow the chemist to perform an organic reaction with high chemoselectivity.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Hands-On Learning / Manipulatives
Reactions

 

Alkene Isomerization Using a Solid Acid as Activator and Support for a Homogeneous Catalyst

Andrew J. Seen
School of Chemistry, University of Tasmania, Launceston, TAS, Australia

 J. Chem. Educ., 2004, 81 (3), p 383
DOI: 10.1021/ed081p383
Publication Date (Web): March 1, 2004

 Abstract
A catalysis experiment has been developed that introduces students to catalysis using an air sensitive transition-metal complex and introduces the use of a solid acid as an activator and support for the catalyst. The experiment is based on the Ni[P(OEt)3]4–H2SO4 alkene isomerization catalyst system, with a solid acid ion exchange resin used in place of H2SO4, providing a safer and easier experiment for undergraduate students. The solid acid ion exchange resin activates the Ni[P(OEt)3]4 complex and immobilizes the resultant cationic nickel species, which can be characterized in situ by UV–vis spectroscopy. The experiment illustrates how immobilization of reagents and catalysts on solid supports provides the opportunity to develop more environmentally acceptable processes by removing potentially corrosive and toxic reagents or catalysts from solution.

 Keywords:
Upper-Division Undergraduate
Inorganic Chemistry
Catalysis

 

One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water

Francesco Fringuelli , Oriana Piermatti and Ferdinando Pizzo
Dipartimento di Chimica, Università di Perugia, 8 - 06123 Perugia, Italy

 J. Chem. Educ., 2004, 81 (6), p 874
DOI: 10.1021/ed081p874
Publication Date (Web): June 1, 2004

 Abstract
7-Hydroxy-3-carboxycoumarin is prepared by a one-pot consecutive process, carried out in water, starting from 2,4-dihydroxybenzaldehyde and malononitrile. The procedure highlights the advantages of using an aqueous medium, particularly the possibility of controlling the pH and isolating the reaction product without using any organic solvent.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry
Hands-On Learning / Manipulatives
Green Chemistry

 

Solvent-Free Synthesis of Chalcones

Daniel R. Palleros
Department of Chemistry and Biochemistry, University of California–Santa Cruz, Santa Cruz, CA 95064

 J. Chem. Educ., 2004, 81 (9), p 1345
DOI: 10.1021/ed081p1345
Publication Date (Web): September 1, 2004

 Abstract
The solvent-free synthesis of 20 chalcones was carried out by grinding the benzaldehyde (unsubstituted, 4-methyl, 4-methoxy, 3-chloro, or 4-chloro) and the acetophenone (unsubstituted, 4-methyl, 4-bromo, or 4-methoxy) in the presence of solid sodium hydroxide with a mortar and pestle. In general, the chalcones were obtained in high yields and high purity. Minor quantities of ketol and Michael addition product were detected by NMR spectroscopy. These side-products were easily removed by recrystallization. The results seem to indicate a correlation between the success of the solvent-free synthesis and the melting point of the chalcone. Chalcones with relatively high melting points (higher than 80°C) were obtained in high yields. The three chalcones that could not be produced in good yields had relatively low melting points.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Green Chemistry

 

Greening the Blue Bottle

Whitney E. Wellman and Mark E. Noble
Department of Chemistry, University of Louisville, Louisville, KY 40292

Tom Healy
Department of Chemistry, Kutztown University, Kutztown, PA 19530

 J. Chem. Educ., 2003, 80 (5), p 537
DOI: 10.1021/ed080p537
Publication Date (Web): May 1, 2003

 Abstract
A new formulation is reported for the Blue Bottle demonstration. The new formulation uses methylene blue and O2 as in the classical Blue Bottle, but ascorbic acid replaces glucose. Instead of half-molar KOH, the solution has a pH of 3. Copper serves as the catalyst.

 Keywords:
High School / Introductory Chemistry
Demonstrations
Tested Demonstrations
Green Chemistry

 

Microwave Synthesis of Tetraphenylporphyrin

Warner, M.; Succaw, G.; Doxsee, K. M.; Hutchison, J. E.
Author Contact: hutch@uoregon.edu

 Summary
In the present experiment students prepare a porphyrin, tetraphenylporphyrin, from four molecules each of pyrrole and benzaldehyde. The carbon framework of the porphyrin is assembled through eight electrophilic substitutions between benzaldehyde and pyrrole to produce a porphyrinogen. Oxidation of the porphyrinogen during the reaction yields the porphyrin (an 18-electron aromatic compound).

 Traditionally, porphyrin syntheses have been carried out in corrosive, high-boiling solvents, such as propionic acid or have been done in large volumes of a halogenated solvent containing a corrosive Lewis acid catalyst. In many cases, toxic oxidizing compounds are used to convert the porphyrinogen to porphyrin. In this experiment, students employ a method of porphyrin synthesis that is solventless-it is carried out on a solid support. The two reagents, pyrrole and benzaldehyde, react on the support under irradiation in a conventional microwave oven. The product is eluted off the solid support with a small amount of solvent. Usually one purifies porphyrins by column chromatography often employing chlorinated solvents such as methylene chloride or chloroform. In this experiment, a safer chromatography solvent mixture (hexanes and ethyl acetate) is used. The link to the laboratory procedures includes pre- and -post lab questions.

 Warner, M.; Succaw, G.; Doxsee, K. M.; Hutchison, J. E. Microwave Synthesis of Tetraphenylporphyrin Greener Approaches to Undergraduate Chemistry Experiments, Print Kirchhoff, M., Ryan, M., Eds.; American Chemical Society: Washington D.C., 2002; pp 27-31.

 

Palladium-Catalyzed Alkyne Coupling/Intramolecular Alkyne Addition: Synthesis of a Benzofuran Product

Gilbertson, R.; Doxsee, K. M.; Succaw, G.; Huffman, L. M.; Hutchison, J. E.
Author Contact: doxsee@uoregon.edu

 Summary
This laboratory module focuses on aqueous organometallic chemistry where a terminal alkyne (2-methyl-3-butyne-2-ol) is coupled with 4-hydroxy-3-iodo-acetophenone in a reaction catalyzed by a palladium complex resulting in the synthesis of a benzofuran product. Traditional palladium-catalyzed alkyne coupling addition methods, involving deprotonated alkynes, are carried out in organic solvent with the careful exclusion of water. The use of metal-catalyzed reactions in water considerably reduces the hazards and environmental impact associated with traditional reactions because the catalyzed reactions can be conducted under mild conditions and they eliminate or reduce the use and disposal of organic solvents.

 This greener synthesis is usually carried out over the course of two lab periods. During the first session, students measure out reagents and set up the reaction and during the second session, students isolate, purify, and characterize the product. The link to the laboratory procedures includes pre- and -post lab questions.

 Gilbertson, R.; Doxsee, K. M.; Succaw, G.; Huffman, L. M.; Hutchison, J. E. Palladium-Catalyzed Alkyne Coupling/Intramolecular Alkyne Addition: Synthesis of a Benzofuran Product Greener Approaches to Undergraduate Chemistry Experiments, Print Kirchhoff, M., Ryan, M., Eds.; American Chemical Society: Washington D.C., 2002; pp 4-7.

 

Organic-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide

Martin Hulce and David W. Marks
Department of Chemistry, Creighton University, Omaha, NE 68178-0104

 J. Chem. Educ., 2001, 78 (1), p 66
DOI: 10.1021/ed078p66
Publication Date (Web): January 1, 2001

 Abstract
Organic-solvent-free oxidations of alcohols using aqueous hydrogen peroxide in the presence of sodium tungstate and phase-transfer catalysts provide a general, safe, simple, and cost-effective means to prepare ketones. Six representative alcohols, 1-phenylethanol, 1-phenylpropanol, benzhydrol, 4-methylbenzhydrol, cis,trans-4-tert-butylcyclohexanol, and benzyl alcohol are oxidized to the corresponding aldehyde or ketone over 1-3 hours in 81-99% yields. Purities are very high, with only small to trace amounts of starting alcohol remaining. Experiments can be readily designed for one or two 3-hour laboratory periods, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.

 Keywords:
Second-Year Undergraduate
Laboratory Instruction
Hands-On Learning / Manipulatives
Catalysis

 

Synthesis and Spectroscopic Analysis of a Cyclic Acetal: A Dehydration Performed in Aqueous Solution

David M. Collard , Adolphus G. Jones and Robert M. Kriegel
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400

 J. Chem. Educ., 2001, 78 (1), p 70
DOI: 10.1021/ed078p70
Publication Date (Web): January 1, 2001

 Abstract
The treatment of aldehydes (and ketones) with diols in the presence of acid gives acetals (and ketals) in an equilibrium reaction. Treatment of pentaerythritol with benzaldehyde in aqueous acid gives the monoacetal, 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane. The reaction has a number of interesting features. The isolated product is the monobenzal not the dibenzal, and the reaction, a dehydration, is performed in water. The reaction proceeds to provide the acetal owing to the insolubility of the product in the aqueous reaction medium, thus removing the product from the equilibrium. This experiment is suitable for incorporation into the undergraduate organic laboratory as the synthesis of a product for characterization by melting point, solubility, and proton nuclear magnetic resonance. Only through recognition of the three-dimensional structure of the dioxane ring can students explain the appearance of the 1H NMR spectrum of the product. The hydroxymethyl groups of the product are inequivalent, as are the hydrogens of the methylenes in the ring. The experiment may also be presented as a group exercise to optimize the conditions of a reaction to maximize the yield of the desired product.

 Keywords:
Upper-Division Undergraduate
Laboratory Instruction
Hands-On Learning / Manipulatives
NMR Spectroscopy

 

"New" Compounds from Old Plastics: Recycling PET Plastics via Depolymerization. An Activity for the Undergraduate Organic Lab

Don Kaufman , Geoff Wright , Ryan Kroemer and Josh Engel
Department of Chemistry, University of Nebraska at Kearney, Kearney, NE 68849

 J. Chem. Educ., 1999, 76 (11), p 1525
DOI: 10.1021/ed076p1525
Publication Date (Web): November 1, 1999

 Abstract
This paper describes work done to develop a meaningful undergraduate organic lab activity that illustrates chemistry of the real world while utilizing reactions typically included in the organic lecture and lab. We show how a common plastic can be converted into several compounds using ester hydrolysis and SN2 reactions. 

Contributing to the critical shortage of landfill space faced by many communities is the large quantity of plastic refuse. Thus, there is a real need to recycle plastic products. One way to recycle plastics such as polyethyleneterephthalate (PET), the polyester from which numerous consumer products such as 2-liter soda bottles are made, is to depolymerize them and then to use the resulting monomers to produce new products. PET is industrially depolymerized via an acid-catalyzed transesterification reaction conducted under conditions of high temperature and pressure that are not feasible in the undergraduate lab. Despite literature reports that PET is remarkably resistant to hydrolysis, we found that PET can be readily hydrolyzed by refluxing with potassium hydroxide or potassium tert-butoxide in amyl alcohol to give terephthalic acid in high yield. It is then possible to readily synthesize terephthalate diesters via SN2 reactions of ammonium terephthalate salts with alkyl halides. Fischer esterification can also be used to prepare the diesters, but yields are significantly lower.

 Keywords:
Second-Year Undergraduate
Organic Chemistry
Hands-On Learning / Manipulatives
Consumer Chemistry