Herasymchuk, Khrystyna published the artcileA New Look at the Competitive Nucleophilic Substitution Reaction in the Pentanol Series, Quality Control of 584-02-1, the main research area is nucleophilic substitution reaction pentanol.
Substitution reactions of alcs. are some of the simplest experiments performed in undergraduate organic chem. laboratory settings. However, the use of gas chromatog. (GC) as an anal. tool for these reactions can be at time laborious and time-consuming. In this work, 1-pentanol, 2-pentanol, 3-pentanol, and 2-methyl-2-butanol were reacted with a 50/50 mixture of ammonium chloride-ammonium bromide in water to yield the corresponding alkyl bromide and alkyl chloride mixtures Aliquots of the reaction mixture were analyzed using proton NMR (1H NMR) spectroscopy and verified by GC. Secondary to secondary carbocation rearrangements were observed in the nucleophilic substitution reactions of 2- and 3-pentanol yielding a mixture of 2- and 3-substituted alkyl halides, while the primary and tertiary alcs. yielded the expected products. Students were assessed on their observations and explanations with the majority of them able to identify the correct reasoning for the alkyl halides mixture formation. 1H NMR spectroscopy provided an inexpensive and quicker method to analyze the mixture and expose the students to the secondary to secondary carbocation rearrangement in the nucleophilic substitution reaction in the pentanol series.
Journal of Chemical Education published new progress about Carbocations. 584-02-1 belongs to class alcohols-buliding-blocks, name is 3-Pentanol, and the molecular formula is C5H12O, Quality Control of 584-02-1.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts