For this problem, we have to draw the complete Fischer esterification mechanism of the reaction below:
The mechanism Fischer esterification follows this series of steps:
(1) Protonation of carbonyl
(2) Nucleophilic attack of alcohol
(3) Proton transfer of -OH to the -OR group
(4) Reformation of C=O group (elimination)
(5) Deprotonation of the C=O+H group
This portion involves loss of H2O from tetrahedral intermediate to form the ester; For remaining steps in mechanism, draw each species resulting from previous step.
Examination of the Fischer esterification mechanism continues.
Overall reaction (ungraded):
Part 1 involved MeOH addition to form the key tetrahedral intermediate. Part 2 involves loss of H2O from the tetrahedral intermediate to form the ester.
Part 2 of 2:
Intermediate species (from Part 1):
Add two curved arrows for the next step.
1) Draw each species (organic and inorganic) resulting from the previous step. Each step will include all of. and only, the atoms given in the first step (i.e., do not use extra re
Make sure you include all species produced by the previous step.
Be sure to:
1) Draw CI-
2) Include all nonbonding electrons on O's and CI to give complete octets.
3) Include the charge, lone pair, and two H's on the bound water O (i.e., protonated alcohol).
4) Use two curved arrows to show the collapse of the tetrahedral intermediate: an OH lone pair moves to form a C=O double bond while a molecule of water eaves, thereby maintaining an octet around that C.
Frequently Asked Questions
What scientific concept do you need to know in order to solve this problem?
Our tutors have indicated that to solve this problem you will need to apply the Fischer Esterification concept. You can view video lessons to learn Fischer Esterification. Or if you need more Fischer Esterification practice, you can also practice Fischer Esterification practice problems.
What is the difficulty of this problem?
Our tutors rated the difficulty ofThis portion involves loss of H2O from tetrahedral intermedi...as medium difficulty.
What professor is this problem relevant for?
Based on our data, we think this problem is relevant for Professor Waas' class at TAMU.