Identify the Hoffmann elimination product formed when 2-bromopentane reacts with sodium tert-butoxid

Question

Identify the Hoffmann elimination product formed when 2-bromopentane reacts with sodium tert-butoxide in tert-butanol.

Professor PC Thomas Classes · Answer

Bulky base (t-butoxide) abstracts the less sterically hindered terminal proton, favoring the less substituted Hofmann alkene.