Question 18.2: What product would you expect from Hofmann elimination of th...
Predicting the Product of a Hofmann Elimination
What product would you expect from Hofmann elimination of the following amine?
S t r a t e g y
The Hofmann elimination is an E2 reaction that converts an amine into an alkene and occurs with non-Zaitsev regiochemistry to form the least highly substituted double bond. To predict the product, look at the reactant and identify the positions from which elimination might occur (the positions two car-bons removed from nitrogen). Then carry out an elimination using the most accessible hydrogen. In the present instance, there are three possible positions from which elimination might occur—one primary, one secondary, and one tertiary. The primary position is the most accessible and leads to the least highly substituted alkene, ethylene.
