The dehydrohalogenation of 2-bromobutane: A simple illustration of anti-Saytzeff elimination as a laboratory experiment for organic chemistry

Leone, Stephen A.; Davis, Justin

doi:10.1021/ed069pa175

Cited by 3 publications

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“…Substitution and elimination reactions are two fundamental reactions taught in undergraduate organic chemistry. − Both reactions are studied substantially in theory, but nucleophilic substitution reactions have garnered more usage in laboratory settings as compared to elimination reactions. − The major problems associated with performing the elimination experiments are the number of products observed and the low boiling points of the formed products. − In this paper, we will show an easy to implement protocol for the acid catalyzed elimination of the pentanol series and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) catalyzed elimination of the bromopentane series using gas chromatography (GC) and proton and carbon nuclear magnetic resonance ( 1 H and 13 C NMR) as analytical tools. We will also show a detailed investigation of the effects of the position of either the hydroxyl or the bromine group on the elimination products under these conditions.…”

Section: Introductionmentioning

confidence: 99%

Revisiting Elimination Reactions in the Pentanol and Bromopentane Series

Raza,

Pattison,

Zhou

et al. 2023

J. Chem. Educ.

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While elimination reactions are ubiquitous in organic chemistry textbooks, their implementation in undergraduate laboratories still suffers from a lack of reliable and easy setup procedures. This paper describes an easy-to-implement set of elimination experiments in the pentanol and bromopentane series using a modified Hickman distillation head. These experiments expose the students to elimination reactions under acidic and basic conditions while analyzing the reaction mixture to determine the stereochemistry of the final products. Additionally, the new safe and green design of these two experiments makes them attractive to implement in large enrollment organic chemistry teaching laboratories in addition to the experiments already available in such settings.

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Section: Introductionmentioning

confidence: 99%

Revisiting Elimination Reactions in the Pentanol and Bromopentane Series

Raza,

Pattison,

Zhou

et al. 2023

J. Chem. Educ.

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Potassiumtert-Heptoxide

Caine

2001

Encyclopedia of Reagents for Organic Synthesis

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Comparable Educational Benefits in Half the Time: An Alternating Organic Chemistry Laboratory Sequence Targeting Prehealth Students

2016

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The laboratory is a mainstay in STEM education, promoting the development of critical thinking skills, dexterity, and scientific curiosity. The goals in the laboratory for nonchemistry, prehealth majors, though, could be distinguished from those for chemistry majors. In service courses such as organic chemistry, much laboratory time is often spent building discipline-specific technical skills that poorly align with the postgraduate goals of prehealth students. To address the needs of students in Muhlenberg College's organic chemistry course for nonchemistry majors, we developed a time-and resourcesaving laboratory sequence that alternates traditional experiments with computer-graded self-guided inquiry activities. This innovative sequence requires approximately half the amount of reagents and fewer staff members, and it offers increased flexibility for students and instructors compared to a traditional (i.e., weekly) lab experience. When this model was offered in 2013− 15, student performances on reports, notebooks, quizzes, exams, and the ACS Organic Chemistry Exam remained consistent with grades in prior course iterations even though students spent less time in lab. Student feedback on this model has been positive, and students felt they were better able to focus on individual lab assignments. We present a detailed overview of this model along with direct and indirect assessment data.

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The dehydrohalogenation of 2-bromobutane: A simple illustration of anti-Saytzeff elimination as a laboratory experiment for organic chemistry

Abstract: A quantitative microscale experiment of the dehydrohalogenation of 2-bromobutane to explore how increasing the base size affects the distribution of products.

Cited by 3 publications

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Revisiting Elimination Reactions in the Pentanol and Bromopentane Series

Revisiting Elimination Reactions in the Pentanol and Bromopentane Series

Potassiumtert-Heptoxide

Comparable Educational Benefits in Half the Time: An Alternating Organic Chemistry Laboratory Sequence Targeting Prehealth Students

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