Sequential Hofmann Elimination Reactions

Part 1.

For each of the following amines (A through D), exhaustive methylation (treatment with excess methyl iodide), followed by Hofmann elimination (heating with AgOH), repeated as necessary, removes the nitrogen atom in the form of trimethylamine. Select a compound by checking one of the buttons to the right of the formulas, and then indicate the number of repetitive Hofmann eliminations required to remove the nitrogen by entering a number (1 to 4) in the designated answer site (red). Finally, draw a structural formula for the hydrocarbon product remaining after all the eliminations are completed. To do so use the drawing window opened by the "Draw Formulas" button. Don't draw hydrohen substituents or specify stereoisomers. When you are finished, "Submit" your formula and then check it by pressing the "Check Answer" button. A help screen is available for the drawing window.

A  
B  
C  
D  
Number of eliminations?


The evaluation window on the right
will display a response to your answer.


   

Part 2.

For some of the following amines (A through D), repetitive exhaustive methylation, followed by Hofmann elimination removes the nitrogen atom in the form of trimethylamine; for others this severing of the nitrogen function is not possible. Select a compound by checking one of the buttons to the right of the formulas, and then indicate whether the nitrogen function can be removed by entering a Yes or No in the designated answer site(red). Finally, draw a structural formula for the product remaining after all the eliminations are completed. To do so use the drawing window opened by the "Draw Formulas" button. Don't specify stereoisomers. When you are finished, "Submit" your formula and then check it by pressing the "Check Answer" button. A help screen is available for the drawing window.

A  
B  
C  
D  
Removal of nitrogen?


This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.
JME Molecular Editor v2002.05 by: by Peter Ertl