Ketone synthesis using household bleach

Perkins, Robert A.; Chau, Felix

doi:10.1021/ed059p981

Cited by 9 publications

(3 citation statements)

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“…Oxidation of alcohols to their corresponding ketones is a common experiment in the organic chemistry laboratory but is most often conducted using either chromic acid or bleach (1)(2)(3)(4)(5)(6)(7). To convert either (+)-menthol to (+)-menthone or (−)-menthol to (−)-menthone, this experiment uses Dess-Martin periodinane as the oxidizing agent, which represents a facile and nontoxic approach to the reaction (8)(9)(10).…”

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Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory

et al. 2005

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Using circular dichroism, organic laboratory students investigated the change in absolute stereochemistry upon oxidation of menthol to menthone. In the first laboratory period, the oxidation was performed with DessMartin periodinane, which is a facile and less toxic oxidizing agent. Half the laboratory group performed the oxidation with (–)-menthol and the other half used (+)-menthol to produce (–)-menthone and (+)-menthone, respectively. The products were analyzed in the second laboratory period using infrared spectroscopy and gas chromatography/mass spectrometry to determine the fraction of starting alcohol converted to ketone. Comparison was made between CD spectra both for the menthol reactant and menthone product and for the (+)- and (–)-menthone enantiomers. A large change in the CD spectrum from reactant to product was diagnostic of successful oxidation. Additionally, the students observed that the circular dichroism spectra of the two enantiomeric products, (–)-menthone and (+)-menthone, are identical in shape but opposite in sign owing to the distinct optical activity of these molecules. Pre- and post-evaluations, completed by the students showed that the learning goal of exposure to CD spectroscopy theory and methods for study of optically active molecules was successful overall.

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confidence: 99%

Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory

et al. 2005

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“…At UGA, traditional oxidation of isoborneol to camphor was performed. , The researchers modified this standard single-outcome experiment to incorporate the use of multiple secondary alcohols as unknown reagents in the oxidation of alcohols to ketones (see Figures and ). The oxidation of alcohols using reagents such as household bleach was reported previously in the literature. ,− However, the development of a multioutcome experiment for the identification of an unknown alcohol with inclusion of benchtop 1 H NMR analysis has yet to be reported.…”

Section: Example Moe: Oxidation Of Alcoholsmentioning

confidence: 98%

Developing and Implementing Multioutcome Experiments in Undergraduate Teaching Laboratories To Promote Student Ownership of the Experience: An Example Multioutcome Experiment for the Oxidation of Alcohols

2019

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Single-outcome experiments are used in the undergraduate instructional laboratory, particularly for large lectures associated with multiple sections of instructional laboratories, due in large part to efficiencies associated with chemical purchases, experiment preparations, and assessments. Despite the practical advantages, single-outcome experiments are not effective in encouraging students to critically analyze and interpret their acquired individual results. Instead, students are satisfied if their results are the same as or similar to all of their classmates’ results, limiting the opportunity for engagement with the laboratory content. In contrast, multioutcome experiments (MOEs) require students to explore the same chemical reaction or transformation but obtain individual results. Individualization of results is accomplished by using a set of starting materials or reagents, one of which is assigned to each student. Students do not know the identity of the assigned component but may be given possible options for its identity. Students elucidate the identity of their individualized products, using modern analytical techniques such as gas chromatography, Fourier-transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy, and deduce the unknown component of their experiment. An example MOE for the oxidation of alcohols is described herein. A traditional single-outcome experiment that utilized a common household oxidizing agent (hypochlorite bleach), rather than a heavy metal-containing alternative, was modified. For the MOE modification, one unknown secondary alcohol (2-pentanol, 3-pentanol, or 3-methyl-2-butanol) was oxidized using bleach. Each student pair was assigned one of three possible unknown alcohols, all of which were constitutional isomers of secondary alcohols. Students knew the identities of the three possible alcohols. Analysis of their oxidation products was accomplished using FTIR and benchtop 1H NMR spectroscopies. Students interpreted their spectra and deduced the identity of the unknown alcohol they were assigned. This experiment provides a tangible framework to understand the applicability of the oxidation reaction and the utility of FTIR and 1H NMR spectroscopies.

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“…This challenge prompted many educators to approach this problem from a pragmatic point of view by using chemicals, equipment, and devices that are available or can be simply transformed from everyday, frequently household materials and tools. The large number of publications on this topic include inter alia analytical, − electrochemical, − synthetic, − and isolation experiments.…”

Section: Introduction Scope and Limitationsmentioning

confidence: 99%

An Integrated Database of Common Chemicals and Chemistry Demonstrations and Student Experiments Used in Hungary

Kovács

Betyár²,

Korom

2021

J. Chem. Educ.

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Chemistry curricula in part rely on the use of laboratory demonstrations and experiments. The complex nature of this kind of educational activity has been posing challenges from the very early days of teaching chemistry. As chemistry is an experimental science, one possible approach to make the teaching of this subject more efficient is to use materials that students encounter in their everyday life. The present paper delineates our efforts to create an integrated database of common chemicals and their use in Hungarian elementary and middle schools. The database combines two seemingly separate but intimately connected fields which has not been accomplished so far: a database of common chemicals and a database of chemistry laboratory demonstration experiments. The two databases with their own idiosyncrasies are connected through a common element, the components present in everyday chemicals. The database offers various levels of searching in both subdatabases and allows pre-and in-service teachers to design their own demonstrations and student experiments, based on common chemicals, that best fit their curricula in context-, project-, inquiry-, discovery-, and phenomenon-based education. The application of our database allows the facilitation of a conceptual change how chemistry and chemicals are contemplated both in and outside school.

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Ketone synthesis using household bleach

Abstract: Household bleach is used to synthesize several different ketones from alcohols.

Cited by 9 publications

References 0 publications

Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory

Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory

Developing and Implementing Multioutcome Experiments in Undergraduate Teaching Laboratories To Promote Student Ownership of the Experience: An Example Multioutcome Experiment for the Oxidation of Alcohols

An Integrated Database of Common Chemicals and Chemistry Demonstrations and Student Experiments Used in Hungary

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