Cart
Article
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
The 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 sample. This article reports a discovery-based experiment that meets both of these criteria. Students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, they conclude that (i) with 1-propanol there is no carbocation rearrangement, (ii) with 2-pentanol there is a considerable degree of secondary-to-secondary carbocation rearrangement, and (iii) with 2,4-dimethyl-3-pentanol all of the alkyl halide formed is the result of a secondary-to-tertiary carbocation rearrangement.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
AlcoholsCiting 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 3 ACS Journal articles (3 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 ...
Probing the Reactivity of Dimethylsulfoxonium Methylide with Conjugated and Nonconjugated Carbonyl Compounds: An Undergraduate Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery
James A. Ciaccio, Elena L. Guevara, Rabeka Alam and Christina D. D’agrosaJournal of Chemical Education2010 87 (8), 850-853Probing the Reactivity of Dimethylsulfoxonium Methylide with Conjugated and Nonconjugated Carbonyl Compounds: An Undergraduate Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery
James A. Ciaccio, Elena L. Guevara, Rabeka Alam and Christina D. D’agrosaJournal of Chemical Education2010 87 (8), 850-853We introduce students to dimethylsulfoxonium methylide (DMSY) epoxidation of aryl and nonconjugated aliphatic aldehydes and ketones without revealing that DMSY cyclopropanates enones by Michael-initiated ring closure (MIRC). Each student performs the ...
A Safer, Discovery-Based Nucleophilic Substitution Experiment
Gail HorowitzJournal of Chemical Education2009 86 (3), 363A Safer, Discovery-Based Nucleophilic Substitution Experiment
Gail HorowitzJournal of Chemical Education2009 86 (3), 363A discovery-based nucleophilic substitution experiment is described in which students compare the reactivity of chloride and iodide ions in an SN2 reaction. This experiment improves upon the well-known "Competing Nucleophiles" experiment in that it does ...
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
