Table of Contents

November 2008
Volume 85, Issue 11
Pages 1467-1584
About the Cover:

Identification of Secondary Metabolites in Citrus Fruits. Jean-Michel Lavoie, Esteban Chornet, and André Pelletier describe an experiment for analytical or organic undergraduate students in which a simple extraction is used to analyze qualitatively and quantitatively monoterpenes in essential oils from citrus fruit peels. Among the fruit tested—limes, grapefruits, and oranges—all showed a high concentration of (R)-limonene, a monoterpenoid commonly found in these fruits. For students, this experiment may be a first contact with the analysis of plant extracts as well as an introduction to the biochemistry of monoterpenes.

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Chemical Education Today

Does Information Want To Be Free?

John W. Moore
p 1467
Publication Date (Web): November 1, 2008 (Editorial)
DOI: 10.1021/ed085p1467
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National Chemistry Week: What Works?

Erica K. Jacobsen
p 1469
Publication Date (Web): November 1, 2008 (Editorial)
DOI: 10.1021/ed085p1469
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Research Advances: Toward an urgently needed antidote for cyanide poisoning disasters; Synthetic rose "petal" effect; Cell phone diagnosis

Angela G. King
p 1470
Publication Date (Web): November 1, 2008 (Report)
DOI: 10.1021/ed085p1470
History, Education, and Documentation

Broadening Participation in Undergraduate Research

Kerry K. Karukstis
p 1474
Publication Date (Web): November 1, 2008 (Report)
DOI: 10.1021/ed085p1474

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

Thomas S. Kuntzleman , David Sellers and Rachel Hoffmeyer
p 1478
Publication Date (Web): November 1, 2008 (Communication)
DOI: 10.1021/ed085p1478

The Origin of the Rotavap

William B. Jensen
p 1481
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1481

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

Laurence Lavelle
p 1482
Publication Date (Web): November 1, 2008 (Commentary)
DOI: 10.1021/ed085p1482
History, Education, and Documentation
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Hydroquinone

Jay A. Young
p 1485
Publication Date (Web): November 1, 2008 (Communication)
DOI: 10.1021/ed085p1485

Biphenyl

Jay A. Young
p 1486
Publication Date (Web): November 1, 2008 (Communication)
DOI: 10.1021/ed085p1486

News and Announcements

JCE staff
p 1487
Publication Date (Web): November 1, 2008 (News and Announcements)
DOI: 10.1021/ed085p1487
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Artistic Periodic Table in Honor of Mendeleev

Antonio Marchal Ingrain
p 1489
Publication Date (Web): November 1, 2008 (Letter)
DOI: 10.1021/ed085p1489.1
History, Education, and Documentation
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French Mnemonics for the Periodic Table

Gilles Olive and David Riffont
p 1489
Publication Date (Web): November 1, 2008 (Letter)
DOI: 10.1021/ed085p1489.2
History, Education, and Documentation
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The Flyleaf Table: An Alternative

Philip J. Stewart
p 1490
Publication Date (Web): November 1, 2008 (Letter)
DOI: 10.1021/ed085p1490
History, Education, and Documentation
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Response to "The Flyleaf Periodic Table"

Laurence Lavelle
p 1491
Publication Date (Web): November 1, 2008 (Letter)
DOI: 10.1021/ed085p1491.1
History, Education, and Documentation
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The Periodic Table: Facts or Committees?

William B. Jensen
p 1491
Publication Date (Web): November 1, 2008 (Letter)
DOI: 10.1021/ed085p1491.2
History, Education, and Documentation
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Author of "The Flyleaf Periodic Table" Responds

Roy W. Clark
p 1493
Publication Date (Web): November 1, 2008 (Letter)
DOI: 10.1021/ed085p1493
History, Education, and Documentation
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Molecules and Medicine (E. J. Corey, Barbara Czakó, and László Kürti)

Robert E. Buntrock
p 1495
Publication Date (Web): November 1, 2008 (Book and Media Review)
DOI: 10.1021/ed085p1495
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Chemistry for Everyone

Communicating about Matter with Symbols: Evolving from Alchemy to Chemistry

Luigi Fabbrizzi
p 1501
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1501
History, Education, and Documentation

In the Classroom

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

Michael J. Samide
p 1512
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1512
History, Education, and Documentation

Saying What You Mean: Teaching Mechanisms in Organic Chemistry

J. Brent Friesen
p 1515
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1515
History, Education, and Documentation

Teaching Organic Synthesis: A Comparative Case Study Approach

David A. Vosburg
p 1519
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1519
History, Education, and Documentation

Novel Organic Courses

Arietta W. Clauss
p 1523
Publication Date (Web): November 1, 2008 (Communication)
DOI: 10.1021/ed085p1523

Percy Julian, Robert Robinson, and the Identity of Eserethole

Addison Ault
p 1524
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1524
History, Education, and Documentation

In the Laboratory

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

Kiel E. Lazarski , Alan A. Rich and Cheryl M. Mascarenhas
p 1531
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1531
History, Education, and Documentation

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

Animesh Aditya , David E. Nichols and G. Marc Loudon
p 1535
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1535
History, Education, and Documentation

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
p 1538
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1538
History, Education, and Documentation

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

Edward M. Treadwell and Tung-Yin Lin
p 1541
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1541
History, Education, and Documentation

Experimental Design and Optimization: Application to a Grignard Reaction

Naoual Bouzidi and Christel Gozzi
p 1544
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1544
History, Education, and Documentation

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

Patty L. Feist
p 1548
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1548
History, Education, and Documentation

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

Molly W. Crowther
p 1550
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1550
History, Education, and Documentation

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

André Pelletier , Jean-Michel Lavoie and Esteban Chornet
p 1555
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1555

Study of Molecular-Shape Selectivity of Zeolites by Gas Chromatography

Shang-Tien Tsai , Pei-Yu Chao , Yao-Yuan Chuang , Grace Hsiuying Ho , Shiow-Huey Chuang and Tseng-Chang Tsai , Chi-Young Lee , Jun-Fu Huang
p 1558
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1558

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

Lee Roecker
p 1562
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1562
History, Education, and Documentation

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

J. Clayton Baum , R. N. Compton and Charles S. Feigerle
p 1565
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1565
History, Education, and Documentation

Research: Science and Education

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

Arthur M. Halpern and Allen Liu
p 1568
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1568
History, Education, and Documentation

Effectiveness of Facilitating Small-Group Learning in Large Lecture Classes

D. C. Lyon and J. J. Lagowski
p 1571
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1571
History, Education, and Documentation

Promoting Student Learning through Group Problem Solving in General Chemistry Recitations

Madhu Mahalingam , Fred Schaefer and Elisabeth Morlino
p 1577
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1577
History, Education, and Documentation

On the Web

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

John Allison
p 1582
Publication Date (Web): November 1, 2008 (Article)
DOI: 10.1021/ed085p1582
History, Education, and Documentation

Molecular Models of Natural Products

William F. Coleman
p 1584
Publication Date (Web): November 1, 2008 (Tech Report)
DOI: 10.1021/ed085p1584
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