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 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
Y
es or
N
o 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?
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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