Journal of Chemical Education

Does Information Want To Be Free?

Thu, 25 Sep 2008 15:03:41 -0000

Editorial
John W. Moore
If you had free online access to all of the content of this Journal, would you pay for a subscription? Think about this for a moment before reading on.

I might. I like to page through the printed copy. I appreciate the care the editorial staff has taken…

National Chemistry Week: What Works?

Thu, 25 Sep 2008 15:03:41 -0000

Especially for High School Teachers
Erica K. Jacobsen
As I write this, the garden is winding down for the season. The time is ripe (pun intended) for reflection. What worked? What didn’t? A new addition this year was zucchini. We tested the waters with just a single plant and it kept us easily supplied for sauteeing with…

Research Advances: Toward an Urgently Needed Antidote for Cyanide Poisoning Disasters; Synthetic Rose "Petal Effect"; Cell Phone Diagnosis

Thu, 25 Sep 2008 15:03:41 -0000

Reports from Other Journals: Research Advances
Angela G. King
Cyanide prophylactic? Roses aid materials science understanding. Using cell phones in medicine…

Broadening Participation in Undergraduate Research

Thu, 25 Sep 2008 15:03:41 -0000

Association Report: CUR
Kerry K. Karukstis
Numerous reports and initiatives are focused on the need to prepare a diverse workforce for the 21st Century. Organizations such as the National Academies, the Committee on Equal Opportunities in Science and Engineering, the Association of American Colleges and Universities, and Building Engineering and Science Talent (BEST) are calling for collective…

"Having a Ball with Chemistry": More Things to Try

Thu, 25 Sep 2008 15:03:41 -0000

Classroom Activity Connections
Thomas S. Kuntzleman, David Sellers, and Rachel Hoffmeyer
A short outreach activity is described in which students test the rebound properties of superballs, racquetballs, "happy" balls and "sad balls" at many temperatures. After conducting the experiment, students use the test results to estimate the glass transition temperature of the elastic polymer that comprises each ball. The activity is used…

The Origin of the Rotavap

Thu, 25 Sep 2008 15:03:41 -0000

Ask the Historian
William B. Jensen
In response to a reader query, the column traces the origins of the laboratory rotary vacuum evaporator or rotavap…

Lanthanum (La) and Actinium (Ac) Should Remain in the d-block

Thu, 25 Sep 2008 15:03:41 -0000

Commentary
Laurence Lavelle
This paper discusses the reasons and implications of placing lanthanum (La) and actinium (Ac) in the f-block and lutetium (Lu) and lawrencium (Lr) in the d-block. The author's conclusion is that placing lanthanum (La) and actinium (Ac) in the f-block results in a less satisfactory presentation of the…

Hydroquinone

Thu, 25 Sep 2008 15:03:41 -0000

CLIP, Chemical Laboratory Information Profile
Jay A. Young
Safe handling and laboratory use of hydroquinone are discussed…

Biphenyl

Thu, 25 Sep 2008 15:03:41 -0000

CLIP, Chemical Laboratory Information Profile
Jay A. Young
Safe handling and laboratory use of biphenyl are discussed…

News & Announcements

Thu, 25 Sep 2008 15:03:41 -0000

JCE news and announcements for this month.

Artistic Periodic Table in Honor of Mendeleev

Thu, 25 Sep 2008 15:03:41 -0000

Letters
Antonio Marachal Ingrain
A large periodic table was placed on the main façade of Sciences Building in the University of Jaén (Spain) in November 2007 to welcome everybody (1). This table was inaugurated by the rector of the University of Jaén and…

French Mnemonics for the Periodic Table

Thu, 25 Sep 2008 15:03:41 -0000

Letters
Gilles Olive and David Riffont
Recently in this Journal (1), Michael et al. proposed some “Multilingual Mnemonics for the Periodic Table”. The example languages were Spanish, English, and German. Memorizing chemical names and symbols can be relatively easy, although the exact horizontal and vertical positions of…

The Flyleaf Table: An Alternative

Thu, 25 Sep 2008 15:03:41 -0000

Letters
Philip J. Stewart
In their consideration of three ways of treating the f-block elements in the standard periodic table, Clark and White opt to footnote a set 15-elements-wide, including both La and Lu, Ac, and Lr (1). Their only grounds seem to be that this…

Response to “The Flyleaf Periodic Table”

Thu, 25 Sep 2008 15:03:41 -0000

Letters
Laurence Lavelle
Clark and White examined 35 introductory and general chemistry textbooks to ascertain which periodic table was most often presented on the flyleaf. Their data show that three versions of the periodic table are most commonly used; however, their data also show that the majority of textbooks use a periodic table with…

The Periodic Table: Facts or Committees?

Thu, 25 Sep 2008 15:03:41 -0000

Letters
William B. Jensen
I would like to offer two observations relative to the recent letter of Clark and White on the representation of the f-block elements in the periodic table that relate to some disturbing trends in the attitudes of the chemical community towards the nature and use of the periodic table&mdash…

The Author of "The Flyleaf Periodic Table" Responds

Thu, 25 Sep 2008 15:03:41 -0000

Letters
Roy W. Clark
Since publication of our letter about the multiple forms of periodic tables presented in the flyleaf of textbooks (1) I have received many replies similar to those of Lavelle and Jensen. To these readers and any others who were puzzled by our recommendation I offer…

The Information Page

Thu, 25 Sep 2008 15:03:41 -0000

The most recent contact and technical information about JCE.

Molecules and Medicine (E. J. Corey, Barbara Czakó, and László Kürti)

Thu, 25 Sep 2008 15:03:41 -0000

Book & Media Reviews
Robert E. Buntrock
Looking for a book on common drugs and pharmaceuticals? On diseases and medical conditions? On pharmacology? In addition, do you need some background in chemistry to handle all of this information? If you want all of this, and in addition want it under one cover, then this is the book for…

Advertising in This Issue

Thu, 25 Sep 2008 15:03:41 -0000

A list of current advertisers in JCE.

Out of the Editor's Basket

Thu, 25 Sep 2008 15:03:41 -0000

Information (press releases) on selected products are collected. Links to the WWW sites of the product manufacturers can be found in the Advertiser's Index for three months after the month of publication…

Communicating about Matter with Symbols: Evolving from Alchemy to Chemistry

Thu, 25 Sep 2008 15:03:41 -0000

Luigi Fabbrizzi
Modern chemists know that alchemists were their historical predecessors, yet they are not proud of this relationship, which chemists today tend to hide or forget. However, no discontinuity exists between alchemy and chemistry and we still use laboratory techniques that were invented by alchemists hundreds or thousands of years ago. Alchemists…

Separation Anxiety: An In-Class Game Designed To Help Students Discover Chromatography

Thu, 25 Sep 2008 15:03:41 -0000

Michael J. Samide
An in-class activity has been developed to assist students in discovering chromatographic separations. Designed on the basis of plate theory, the game has students use instructor-provided partition coefficients to establish equilibrium for two different items between a stationary and mobile phase. As students work through equilibration and mobile phase…

Saying What You Mean: Teaching Mechanisms in Organic Chemistry

Thu, 25 Sep 2008 15:03:41 -0000

J. Brent Friesen
Organic reactions in introductory organic chemistry courses are most commonly taught with a mechanism-based approach to the understanding of molecular reactivity. However, the effectiveness of the popular curved arrow representation to describe reaction mechanisms is often compromised by the overuse of shortcuts and obscure notation. The consistent use of balanced…

Teaching Organic Synthesis: A Comparative Case Study Approach

Thu, 25 Sep 2008 15:03:41 -0000

David A. Vosburg
In this course, students encounter reactions and mechanisms in the context of landmark syntheses of biologically important molecules. Students closely examine pairs of syntheses of related or identical molecules to facilitate their appreciation for synthetic strategy. They then write short, creative papers that critically compare the two synthetic routes. Teams of…

Novel Organic Courses

Thu, 25 Sep 2008 15:03:41 -0000

Arietta W. Clauss
JCE offers a wealth of materials for teaching and learning chemistry. Below are some additional resources for teaching organic chemistry suggested by Arrietta Clauss of the Editorial Staff that are available through JCE.…

Percy Julian, Robert Robinson, and the Identity of Eserethole

Thu, 25 Sep 2008 15:03:41 -0000

Addison Ault
The Nova production Percy Julian—Forgotten Genius included the very public disagreement between Percy Julian, an unknown American chemist, and Robert Robinson, possibly the best known organic chemist of the day, as to the identity of "eserethole", the key intermediate for the synthesis of the alkaloid…

A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory

Thu, 25 Sep 2008 15:03:41 -0000

Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas
The Robinson annulation is a topic of importance in the second-year organic curriculum. A one-pot, enantioselective Robinson annulation is described. The experiment is completed in two lab periods and is geared towards the second-year organic chemistry major. To our knowledge, this is the first example of a one…

Borohydride Reduction of Estrone. Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory

Thu, 25 Sep 2008 15:03:41 -0000

Animesh Aditya, David E. Nichols, and G. Marc Loudon
This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly diastereoselective manner. The diastereomeric estradiols produced in the reaction can be analyzed and differentiated by thin-layer chromatography…

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

Thu, 25 Sep 2008 15:03:41 -0000

Green Chemistry
Xavier Sauvage and Lionel Delaude
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…

A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and Acetanilides

Thu, 25 Sep 2008 15:03:41 -0000

Edward M. Treadwell and Tung-Yin Lin
An experiment is described involving the nitration of ortho or meta monosubstituted benzoic acids (XC₆H₄CO₂H, X = Halogen, Me, OH, or OMe) and monochlorinated acetanilides with nitric acid to determine the regioselectivity of addition by ¹H NMR…

Experimental Design and Optimization: Application to a Grignard Reaction

Thu, 25 Sep 2008 15:03:41 -0000

Naoual Bouzidi and Christel Gozzi
This project is conducted by students during the second semester of their second year in our educational institution. This project constitutes an initiation into research and allows a broadening of knowledge, a development in autonomy, organization, team work, and initiative. It helps prepare the student-engineer for an internship in industry…

The Synthesis of a Cockroach Pheromone. An Experiment for the Second-Year Organic Chemistry Laboratory

Thu, 25 Sep 2008 15:03:41 -0000

Patty L. Feist
This experiment describes the synthesis of gentisyl quinone isovalerate, or blattellaquinone, a sex pheromone of the German cockroach that was isolated and identified in 2005. The synthesis is appropriate for the second semester of a second-year organic chemistry laboratory course. It can be completed in two, three-hour laboratory periods…

NMR and IR Spectroscopy for the Structural Characterization of Edible Fats and Oils. An Instrumental Analysis Laboratory

Thu, 25 Sep 2008 15:03:41 -0000

Molly W. Crowther
This article describes an upper-level instrumental laboratory for undergraduates that explores the complementary nature of IR and NMR spectroscopy for analysis of several edible fats and oils that are structurally similar but differ in physical properties and health implications. Five different fats and oils are analyzed for average chain length…

Identification of Secondary Metabolites in Citrus Fruit Using Gas Chromatography and Mass Spectroscopy

Thu, 25 Sep 2008 15:03:41 -0000

Jean-Michel Lavoie, Esteban Chornet, and André Pelletier
This experiment targets undergraduate students in an analytical or organic instructional context. Using a simple extraction, this protocol allows students to quantify and qualify monoterpenes in essential oils from citrus fruit peels. The procedures involve cooling down the peels by immersing them into icy water. After a few minutes, the chilled…

Study of Molecular-Shape Selectivity of Zeolites by Gas Chromatography

Thu, 25 Sep 2008 15:03:41 -0000

Pei-Yu Chao, Yao-Yuan Chuang, Grace Hsiuying Ho, Shiow-Huey Chuang, Tseng-Chang Tsai, Chi-Young Lee, Shang-Tien Tsai, and Jun-Fu Huang
A sorption experiment using a gas chromatograph is described that can help students understand the "molecular-shape selectivity" behavior of zeolites in the subnano regime. Hexane isomers are used as probe molecules to demonstrate the sorption phenomena. In the experiment, a zeolite adsorbs certain hexane isomers with molecular sizes smaller than…

Synthesis and Base Hydrolysis of a Cobalt(III) Complex Coordinated by a Thioether Ligand

Thu, 25 Sep 2008 15:03:41 -0000

Lee Roecker
A two-week laboratory experiment for students in advanced inorganic chemistry is described. Students prepare and characterize a cobalt(III) complex coordinated by a thioether ligand during the first week of the experiment and then study the kinetics of Co–S bond cleavage in basic solution during the second week…

Laser Measurement of the Speed of Sound in Gases: A Novel Approach to Determining Heat Capacity Ratios and Gas Composition

Thu, 25 Sep 2008 15:03:41 -0000

J. Clayton Baum, R. N. Compton, and Charles S. Feigerle
The speed of sound is measured in several gases using a pulsed laser to create a micro-spark on a carbon rod and a microphone connected to a digital oscilloscope to measure the time-of-flight of the resulting shockwave over a known distance. These data are used to calculate the…

Gas Nonideality at One Atmosphere Revealed Through Speed of Sound Measurements and Heat Capacity Determinations

Thu, 25 Sep 2008 15:03:41 -0000

Arthur M. Halpern and Allan Liu
Using an easy-to-make cylindrical resonator, students can measure the speed of sound in a gas, u, with sufficiently high precision (by locating standing-wave Lissajous patterns on an oscilloscope) to observe real gas properties at one atmosphere and 300 K. For CO₂ and SF…

Effectiveness of Facilitating Small-Group Learning in Large Lecture Classes. A General Chemistry Case Study

Thu, 25 Sep 2008 15:03:41 -0000

Chemical Education Research
D. C. Lyon and J. J. Lagowski
We report the results of a study designed to investigate the effectiveness of peer-led, small-group discussions in a large (N > 400) general chemistry course usually taught in a traditional lecture format. The administrative structure, the training of the peer facilitators, and the achievement of students exposed to…

Promoting Student Learning through Group Problem Solving in General Chemistry Recitations

Thu, 25 Sep 2008 15:03:41 -0000

Madhu Mahalingam, Fred Schaefer, and Elisabeth Morlino
We describe the implementation and effects of group problem solving in recitation sections associated with the general chemistry course at a small private science university. Recitation sections of approximately 45 students are used to supplement large (approximately 180 students) lecture sections. The primary goal of recitation is working in small groups…

Mass Spectrometry Theatre: A Model for Big-Screen Instrumental Analysis

Thu, 25 Sep 2008 15:03:41 -0000

Computer Bulletin Board
John Allison
Teaching lecture or lab courses in instrumental analysis can be a source of frustration since one can only crowd a small number of students around a single instrument, typically leading to round-robin approaches. Round-robin labs can spread students into multiple labs and limit instructor–student interactions. We discuss…

Molecular Models of Natural Products

Thu, 25 Sep 2008 15:03:41 -0000

JCE Featured Molecules
William F. Coleman
This month’s issue of the Journal includes several papers discussing interesting molecules that fall into the broad category of natural products, and four of these papers serve as the source for our featured molecules this time around. Addison Ault weaves an interesting tale of the search for…