Cart
Article
A Discovery-Based Friedel-Crafts Acylation Experiment: Student-Designed Experimental Procedure
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
A discovery-based Friedel–Crafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context. The reaction proceeds in 50–85% isolated yield following a simple extractive workup. 1H NMR spectroscopy is used to identify the para-substituted acetophenone product, which leads to the identification of the starting material. Semi-empirical calculations are performed on molecular models of the ortho- and para-substituted acetophenone isomers to assess the thermodynamic stability of each, providing an explanation for the lack of ortho isomer in the reaction.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
Aromatic CompoundsCiting Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 6 ACS Journal articles (5 most recent appear below).
IR Cards: Inquiry-Based Introduction to Infrared Spectroscopy
Jacqueline Bennett and Tabetha ForsterJournal of Chemical Education2010 87 (1), 73-77IR Cards: Inquiry-Based Introduction to Infrared Spectroscopy
Jacqueline Bennett and Tabetha ForsterJournal of Chemical Education2010 87 (1), 73-77As infrared spectroscopy (IR) is frequently used in undergraduate organic chemistry courses, an inductive introduction to IR spectroscopy that uses index cards printed with spectra, structures, and chemical names is described. Groups of students are given ...
Integrating Computational Molecular Modeling into the Undergraduate Organic Chemistry Curriculum
Allen D. Clauss and Stephen F. NelsenJournal of Chemical Education2009 86 (8), 955Integrating Computational Molecular Modeling into the Undergraduate Organic Chemistry Curriculum
Allen D. Clauss and Stephen F. NelsenJournal of Chemical Education2009 86 (8), 955An instructional unit is described for integrating computational molecular modeling into the undergraduate organic chemistry laboratory curriculum. The approach emphasizes use of computational modeling as a readily available, efficient tool for ...
JCE Concept Connections: Computational Molecular Modeling
Xavier Prat-Resina and Bernadette CaldwellJournal of Chemical Education2009 86 (8), 958JCE Concept Connections: Computational Molecular Modeling
Xavier Prat-Resina and Bernadette CaldwellJournal of Chemical Education2009 86 (8), 958The Journal has published many resources on computational molecular modeling and using this approach with organic chemistry.
Using Student-Developed, Inquiry-Based Experiments To Investigate the Contributions of Ca and Mg to Water Hardness
Shui-Ping Yang and Chung-Chia LiJournal of Chemical Education2009 86 (4), 506Using Student-Developed, Inquiry-Based Experiments To Investigate the Contributions of Ca and Mg to Water Hardness
Shui-Ping Yang and Chung-Chia LiJournal of Chemical Education2009 86 (4), 506This study provided a challenging opportunity for general chemistry students to mimic the scientific research process by solving a water-quality problem concerning individual calcium and magnesium concentrations. We found that general chemistry students ...
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides
Richard A. Kjonaas and Ryand J. F. TuckerJournal of Chemical Education2008 85 (1), 100A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides
Richard A. Kjonaas and Ryand J. F. TuckerJournal of Chemical Education2008 85 (1), 100The use of permanent magnet 13C NMR in large-section first-semester organic chemistry lab courses is limited by the availability of experiments that not only hinge on first-semester lecture topics, but which also produce at least 0.5 mL of neat liquid ...
Full Text HTMLTools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Received: August 03, 2009
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
