The Hofmann Rearrangement Using Household Bleach: Synthesis of 3-Nitroaniline

Monk, Keith A.; Mohan, Ram S.

doi:10.1021/ed076p1717

Cited by 7 publications

(6 citation statements)

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“…To enhance understanding, hands-on experimentation is recommended to render these concepts tangible. 9 Although experimental designs for rearrangement reactions have been introduced into laboratory education, such as Favorskii rearrangement, 10,11 Hofmann rearrangement, 12 Fries rearrangement, 13 and Pinacol rearrangement, 14 discussions on the regional selectivity of rearrangement reactions remain sparse. Therefore, the introduction of a regioselective rearrangement reaction into undergraduate experimental education holds profound importance.…”

Section: ■ Introductionmentioning

confidence: 99%

“…15,16 Moreover, carbon-to-carbon (C → C) migration dominates rearrangement reactions applied in undergraduate laboratories, while carbonto-nitrogen (C → N) migrations are rarely involved. 17 Such C → N migrations generate new carbon−nitrogen bonds within molecular skeletons, 15,16,18,19 thereby offering the potential to achieve amide products with bioactivity or specific function.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Although experimental designs for rearrangement reactions have been introduced into laboratory education, such as Favorskii rearrangement, , Hofmann rearrangement, Fries rearrangement, and Pinacol rearrangement, discussions on the regional selectivity of rearrangement reactions remain sparse.…”

Section: Introductionmentioning

confidence: 99%

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Introducing Regioselectivity in Rearrangement Reactions through a Discovery Experiment Using an Improved Schmidt-Type Reaction

Chen,

Zeng,

et al. 2024

J. Chem. Educ.

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Rearrangement reactions, one of the most important transformations in organic chemistry, represent an important yet difficult aspect of the discipline. However, rearrangement reactions that involve regioselectivity are rarely covered in traditional experimental textbooks. Herein, a novel organic chemistry laboratory experiment centered around a Schmidt-type rearrangement was designed and presented, aimed at elucidating the mechanism of this reaction and its regioselective nature for students. Before conducting the experiment, students are tasked with previewing the mechanism underlying the formation of the observed amide product from the reaction between 4-nitrobenzophenone and n-PrNO 2 . Given the asymmetric nature of the ketone, the potential for obtaining different amide products depends on the priority of the migration of the two aryls of 4-nitrobenzophenone during rearrangement. Through this experiment, students can discover that the product arises from the migration of the more electron-rich aryl, thereby indicating a nucleophilic rearrangement with evident regioselectivity. Additionally, the concept of green chemistry was integrated into the organic chemistry curriculum, underscoring the contribution of this improved Schmidt-type reaction in reducing toxicity and enhancing safety. This approach prompts students to recognize the imperative of green chemistry in advancing sustainable societal development, emphasizing the collective responsibility of chemists to shoulder environmentally conscious practices.

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Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Introducing Regioselectivity in Rearrangement Reactions through a Discovery Experiment Using an Improved Schmidt-Type Reaction

Chen,

Zeng,

et al. 2024

J. Chem. Educ.

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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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“…As such, a plethora of methods for the construction of these motifs have been developed. 5 Traditional protocols (nucleophilic substitutions, 6 rearrangements of primary amides, 7 the two-step reductive amination of aromatic aldehydes/ketones, 8 or the 1,2addition of carbon nucleophiles into a C-N-double bond 9,10 ) are broadly applicable but do have severe limitations that are partially due to the specific nature of the nucleophilic nitrogen atom (e.g. overalkylation, elimination).…”

mentioning

confidence: 99%