Organic Chem Esterification
EXPERIMENT 5- A FISCHER ESTERIFICATION SYNTHESIS OF PEAR OIL
One of the major uses of Esterification (C(=O)-C-R) is forming compounds with different odors which can be used to make different synthetic and natural flavorings. Using the chemical and physical properties of organic compounds, an ester was catalyzed from the reaction of a carboxylic acid with an alcohol, producing an odor similar to that of pear oil. The mechanism of this Fischer- Esterification process is outlined as follows: Carboxylic Acid Alcohol (fig.1) Ester water
Particularly, 1-hexanol was reacted with an excess of acetic acid, using an acid catalyst to yield its ester: hexyl acetate. The reaction was performed under reflux which sped up the reaction by continuous vapor-condensation cycles of the solution mixture as the solution boiled. The vapors were blocked from escaping the solution by a stream of cold water running up the reflux column. Also, to increase the reaction rate, an acid catalyst: sulfuric acid, was added to the reactant mixture (³). The main reaction is as follows:
However, the actual reaction does not only produce the expected ester and water but also unreacted reactants along with byproducts; the actual mixture contains:
Hexyl Alcohol (aq) + Acetic Acid (aq) Hexyl Acetate (l) + H2O (aq) + H2SO4 (aq) + Acetic Acid (aq) +hexanol(aq) +Byproducts
To produce a better yield, le chatelier’s principle was applied which states that increasing the amount of a compound will force the reaction in the opposite direction; having an excess of the acetic acid, allowed the
One of the major uses of Esterification (C(=O)-C-R) is forming compounds with different odors which can be used to make different synthetic and natural flavorings. Using the chemical and physical properties of organic compounds, an ester was catalyzed from the reaction of a carboxylic acid with an alcohol, producing an odor similar to that of pear oil. The mechanism of this Fischer- Esterification process is outlined as follows: Carboxylic Acid Alcohol (fig.1) Ester water
Particularly, 1-hexanol was reacted with an excess of acetic acid, using an acid catalyst to yield its ester: hexyl acetate. The reaction was performed under reflux which sped up the reaction by continuous vapor-condensation cycles of the solution mixture as the solution boiled. The vapors were blocked from escaping the solution by a stream of cold water running up the reflux column. Also, to increase the reaction rate, an acid catalyst: sulfuric acid, was added to the reactant mixture (³). The main reaction is as follows:
However, the actual reaction does not only produce the expected ester and water but also unreacted reactants along with byproducts; the actual mixture contains:
Hexyl Alcohol (aq) + Acetic Acid (aq) Hexyl Acetate (l) + H2O (aq) + H2SO4 (aq) + Acetic Acid (aq) +hexanol(aq) +Byproducts
To produce a better yield, le chatelier’s principle was applied which states that increasing the amount of a compound will force the reaction in the opposite direction; having an excess of the acetic acid, allowed the