A Multioutcome Experiment for the Williamson Ether Synthesis

Abstract

Williamson ether experiments are commonly performed by students in undergraduate organic chemistry instructional laboratory courses. In this multioutcome experiment, students were provided 4-bromophenol and one of three alkyl halides: 1-bromopentane, 1-bromobutane, or 1-bromo-3-methylbutane. The alkyl halides served as the unknown component of the experiment, and students were given these three as unknown candidates. After isolating the product from the reaction mixture, students analyzed their products using FT-IR and benchtop 1H NMR spectroscopies. The experimental results herein summarize the inclusion of this experiment in the large enrollment second-semester organic chemistry laboratory course over four semesters.

Incorporating Benchtop NMR Spectrometers in the Undergraduate Lab: Understanding Resolution and Circumventing Second-Order Effects

“…19 Notably, Morrison and co-workers have also published several works highlighting the option for inclusion of multioutcome experiments through the use of hands-on NMR spectroscopy. 20,21 While the size, cost, and maintenance characteristics of benchtop NMR address the accessibility issues, the low-field aspect of these magnets introduces new concerns: sensitivity, resolution, dispersion, and spectral complexity. While sensitivity is inherently reduced at low field, this is often easily overcome at an undergraduate level by increasing the concentration of the sample.…”

“…The emergence of benchtop NMR spectrometers in the early 2010s was well-received by undergraduate laboratory instructors, as evidenced by a sharp increase in the number of academic publications which showcase feasible experiments for hands-on instrument usage − as well as within academic and industrial research. − Additionally it allowed NMR spectroscopy to be included in teaching and outreach initiatives including the Royal Society of Chemistry’s (RSC) Spectroscopy in a Suitcase (SIAS) program and the Scottish NMR User’s Group (SNUG) . Notably, Morrison and co-workers have also published several works highlighting the option for inclusion of multioutcome experiments through the use of hands-on NMR spectroscopy. , While the size, cost, and maintenance characteristics of benchtop NMR address the accessibility issues, the low-field aspect of these magnets introduces new concerns: sensitivity, resolution, dispersion, and spectral complexity.…”

Pemanfaatan Iradiasi Gelombang Mikro pada Sintesis Metil orto-metoksisinamat

“…Reaksi antara ion fenoksida dengan dimetilsulfat mengikuti sintesis eter Williamson, yaitu substitusi nukleofilik bimolekular (SN 2 ). Sintesis eter aromatis melalui pembentukan ion fenoksida dapat juga diperoleh dengan menggunakan kondisi basa KOH dengan katalis fase transfer tetra butil ammonium bromide untuk senyawa fenol yang tidak larut air mengikuti mekanisme reaksi SN 2 [13,14].…”

“…Hal tsb menunjukkan bahwa proton pada Cα dan Cβ alkena berada pada konformasi trans [19]. Adanya dua metil pada senyawa hasil sintesis, terkonfirmasi pada geseran kimia 3.79 ppm dan 3.74 ppm pada spektra 1 HNMR, yang diperkuat pada spektra 13 CNMR geseran kimia 51.2 dan 55.5 ppm.…”

Bio-Based Aromatic Copolyesters: Influence of Chemical Microstructures on Thermal and Crystalline Properties

“…In this study, starting from the renewable nipagin and eugenol, two kinds of diester monomers were synthesized via thiol-ene click chemistry and SN2 reactions [39,40]. Random copolymerization was then carried out in the predetermined composition ratios of diester monomers with another renewable monomer, 1,6-hexanediol, as a comonomer [41,42].…”