What is the major Hofmann elimination product formed from the below amine?

Question:

What is the major Hofmann elimination product formed from the below amine?

Hofmann Elimination Product:

Quaternary ammonium salt reacts with an alkyl iodide. Further action of silver oxide, water, and optimum heat on the intermediate quaternary ammonium iodide results in a tertiary amine and a least stable, less substituted alkene as a major Hofmann elimination product.

Answer and Explanation: 1

Given Data

The major product will come from Hofmann's elimination of the following amine,


We can redraw the structure in the following simple equivalent form.


The easiest way to predict the major Hofmann elimination product is as follows:

1. Remove the {eq}- {\rm{N}}{{\rm{H}}_2} {/eq} group.

2. Remove the hydrogen atom directly attached to the carbon atom adjacent to the carbon where the amino group was attached.

3. Place a double bond between the carbons from where the amino group and hydrogen atom were subsequently removed.

Thus, working on this method, we get an alkene product with the following structure.


Thus, the major product of the given Hofmann reaction is drawn above.


Learn more about this topic:

Amine Reactions: Practice Problems
Amine Reactions: Practice Problems

from

Chapter 4 / Lesson 15
224

In this lesson, we will practice reactions that involve amines. This includes reactions that synthesize amines and reactions that amines can participate in.


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