Problem: 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 reMake 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.

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FREE Expert Solution

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

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Problem Details

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.