Cart
Article
The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
Based on previously described experiments on the Ritter reaction between tert-butyl alcohol and benzonitrile in the presence of concentrated sulfuric acid and on the analysis of three computed hypothetical pathways, also previously described, Ritter reactions using the remaining three isomeric butyl alcohols in which Wagner-Meerwein rearrangements can take place are performed. From this information students are able to propose a mechanism for the Ritter reaction compatible with the experimental evidence they themselves obtained. The reactions are run simultaneously by groups of students under very simple experimental conditions, the reference compounds are prepared and characterized using melting point determination and IR and 1H NMR spectroscopy, and the reaction products are identified by TLC. Since the students have to share samples and information, they have a fruitful, cooperative learning experience.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Collaborative / Cooperative LearningKeywords (Subject):
Mechanisms of ReactionsCiting 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).
Carbocation Rearrangement in an Electrophilic Aromatic Substitution Discovery Laboratory
Victoria Polito, Christian S. Hamann and Ian J. RhileJournal of Chemical Education2010 87 (9), 969-970Carbocation Rearrangement in an Electrophilic Aromatic Substitution Discovery Laboratory
Victoria Polito, Christian S. Hamann and Ian J. RhileJournal of Chemical Education2010 87 (9), 969-970In this discovery laboratory, students performed electrophilic aromatic substitution reactions between 1,4-dimethoxybenzene and either 2-methyl-2-butanol or 3-methyl-2-butanol with sulfuric acid as a catalyst. The carbocation from 3-methyl-2-butanol ...
Silver- and Gold-Catalyzed Intramolecular Rearrangement of Propargylic Alcohols Tethered with Methylenecyclopropanes: Stereoselective Synthesis of Allenylcyclobutanols and 1-Vinyl-3-oxabicyclo[3.2.1]octan-8-one Derivatives
Liang-Feng Yao, Yin Wei and Min ShiThe Journal of Organic Chemistry2009 74 (24), 9466-9469Silver- and Gold-Catalyzed Intramolecular Rearrangement of Propargylic Alcohols Tethered with Methylenecyclopropanes: Stereoselective Synthesis of Allenylcyclobutanols and 1-Vinyl-3-oxabicyclo[3.2.1]octan-8-one Derivatives
Liang-Feng Yao, Yin Wei and Min ShiThe Journal of Organic Chemistry2009 74 (24), 9466-9469Ag(I)-catalyzed intramolecular reaction of monoarylmethylenecyclopropanes (MCPs) tethered with 1,1,3-triarylprop-2-yn-1-ols provides diastereoselective access to polysubstituted allenylcyclobutanols and the obtained allenylcyclobutanols catalyzed by Au(I) ...
Large Amplitude, Proton- and Cation-Activated Latch-Type Mechanical Switches: O-Protonated Amides Stabilized by Intramolecular, Low-Barrier Hydrogen Bonds within Macrocycles
Mariappan Kadarkaraisamy, Gerald Caple, Andrea R. Gorden, Marie A. Squire and Andrew G. SykesInorganic Chemistry2008 47 (24), 11644-11655Large Amplitude, Proton- and Cation-Activated Latch-Type Mechanical Switches: O-Protonated Amides Stabilized by Intramolecular, Low-Barrier Hydrogen Bonds within Macrocycles
Mariappan Kadarkaraisamy, Gerald Caple, Andrea R. Gorden, Marie A. Squire and Andrew G. SykesInorganic Chemistry2008 47 (24), 11644-11655Reduction of an anthraquinone macrocycle and reaction with nitriles and primary amides under Ritter amide conditions yields protonated oxonium ions stabilized by an intramolecular hydrogen bond. Short, Low-Barrier Hydrogen Bonds (LBHB) are formed, ...
Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography. A Microscale Experiment for Organic Chemistry
Benjamin T. Burlingham and Joseph C. RettigJournal of Chemical Education2008 85 (7), 959Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography. A Microscale Experiment for Organic Chemistry
Benjamin T. Burlingham and Joseph C. RettigJournal of Chemical Education2008 85 (7), 959A microscale experiment is presented in which cyclohexene is dihydroxylated under three sets of conditions: epoxidation–hydrolysis, permanganate oxidation, and the Woodward dihydroxylation. The products of the reactions are determined by the use of thin-...
A Nitration Reaction Puzzle for the Organic Chemistry Laboratory
Milton J. Wieder and Russell BarrowsJournal of Chemical Education2008 85 (4), 549A Nitration Reaction Puzzle for the Organic Chemistry Laboratory
Milton J. Wieder and Russell BarrowsJournal of Chemical Education2008 85 (4), 549Treatment of phenylacetic acid with 90% HNO3 yields a product, I, whose observed melting point is 175–179 °C and whose equivalent weight is approximately 226 grams. Treatment of phenylacetic acid with 70% HNO3 yields a product, II, whose observed melting ...
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
