Please provide a mechanism with curved arrows for this reaction.

EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN:9781305446021
Author:Lampman
Publisher:Lampman
Chapter8: Acetylsalicylic Acid
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Please provide a mechanism with curved arrows for this reaction.

Experiment 8: Fischer Esterification (Data Sheet)
Running the reaction
1.20 mL of isopentyl alcohol and 1.70 mL of glacial acetic acid were placed in a 5 mL
conical vial
Three drops of concentrated sulfuric acid were added
An air condenser (cooled with a wet paper towel) was added and the mixture was gently
refluxed for 60 minutes
Upon cooling, two layers form: the smaller layer making the bottom layer
Product isolation
After the removal of the air condenser, 1 mL of 5 % sodium bicarbonate solution was
added; the mixture was gently mixed leading to foaming (CO2 formation); the bottom layer
was removed
Two more extractions with 1 mL of 5 % sodium bicarbonate solution were performed, the
last one barely leading to any bubble formation
The organic layer was transferred to a clean test tube and dried over three microspatulas of
anhydrous sodium sulfate
The dry organic layer was transferred to a 3 mL conical vial; a Hickman head is attached
and a thermometer placed inside the Hickman head
The crude was distilled until only two drops remained in the vial
Product characterization
1.05 g of the product
B.p.: 138.5-141.5 °C
Refractive index: np18= 1.3980
Transcribed Image Text:Experiment 8: Fischer Esterification (Data Sheet) Running the reaction 1.20 mL of isopentyl alcohol and 1.70 mL of glacial acetic acid were placed in a 5 mL conical vial Three drops of concentrated sulfuric acid were added An air condenser (cooled with a wet paper towel) was added and the mixture was gently refluxed for 60 minutes Upon cooling, two layers form: the smaller layer making the bottom layer Product isolation After the removal of the air condenser, 1 mL of 5 % sodium bicarbonate solution was added; the mixture was gently mixed leading to foaming (CO2 formation); the bottom layer was removed Two more extractions with 1 mL of 5 % sodium bicarbonate solution were performed, the last one barely leading to any bubble formation The organic layer was transferred to a clean test tube and dried over three microspatulas of anhydrous sodium sulfate The dry organic layer was transferred to a 3 mL conical vial; a Hickman head is attached and a thermometer placed inside the Hickman head The crude was distilled until only two drops remained in the vial Product characterization 1.05 g of the product B.p.: 138.5-141.5 °C Refractive index: np18= 1.3980
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