Presenter(s)
Natalie Olsen
Abstract
The main goal of this research was to demonstrate the occurrence of allylic rearrangement in the reaction of N-bromosuccinimide (NBS) with 2-heptene. Thus, we aimed to demonstrate using 1H NMR and HPLC that (E)-2-bromo-3-heptene (E-2-3) and (E)-4-bromo-2-heptene (E-4-2) are formed in roughly equal amounts. This is important because several references claim that allylic rearrangement does not occur to a significant extent in this reaction. The reaction was run using 2.1mL (15 mmol) of 2-heptene, 1.84 g of NBS (10 mmol), and 0.008g of benzoyl peroxide (0.03 mmol), in cyclohexane (9.4 mL) under reflux. 1H NMR of the product mixture clearly showed the formation of both products (43% E-2-3, 37% E-4-2), which we attempted to isolate by HPLC.
College
College of Science & Engineering
Department
Chemistry
Campus
Winona
First Advisor/Mentor
Tom Nalli
Location
Kryzsko Great River Ballroom, Winona, Minnesota; United States
Start Date
4-23-2026 1:00 PM
End Date
4-23-2026 2:00 PM
Presentation Type
Poster Session
Format of Presentation or Performance
In-Person
Session
2a=1pm-2pm
Poster Number
47
N-Bromosuccinimide Bromination of 2-Heptene: Determination of all Allylic Bromide Products
Kryzsko Great River Ballroom, Winona, Minnesota; United States
The main goal of this research was to demonstrate the occurrence of allylic rearrangement in the reaction of N-bromosuccinimide (NBS) with 2-heptene. Thus, we aimed to demonstrate using 1H NMR and HPLC that (E)-2-bromo-3-heptene (E-2-3) and (E)-4-bromo-2-heptene (E-4-2) are formed in roughly equal amounts. This is important because several references claim that allylic rearrangement does not occur to a significant extent in this reaction. The reaction was run using 2.1mL (15 mmol) of 2-heptene, 1.84 g of NBS (10 mmol), and 0.008g of benzoyl peroxide (0.03 mmol), in cyclohexane (9.4 mL) under reflux. 1H NMR of the product mixture clearly showed the formation of both products (43% E-2-3, 37% E-4-2), which we attempted to isolate by HPLC.
Comments
Olsen, Natalie L