1. In an experiment where Glacial Acetic Acid (the Carboxylic Acid) and 1-Butanol (the Alcohol) react with concentrated (18M) Sulfuric Acid (H2SO4), then adding water to pass through this mixture and draining the bottom aqueous layer, then doing the same with saturated sodium bicarbonate (NaHCO3) (draining bottom layer), and finally with saturated sodium chloride (NaCl) (draining bottom layer), some Anhydrous Sodium Sulfate (Na2SO4) is added to remove the water from the product. The final product should be Butyl Acetate.
The overall reaction:
Glacial Acetic Acid + 1-Butanol --> Butyl Acetate
or
Chemical Formula of overal reaction:
CH3COOH + C4OH10 --> C6H12O2
a.)
Provide a full mechanism for a possible SN2 side-reaction that may occur under the experimental conditions; include all charges and intermediates. To achieve full marks, use arrows to clearly show bonds forming or breaking between atoms. Vaguely directed arrows will not receive marks. (2.5 Marks)
b.)
Would you expect the side product to be in the purified (i.e. distilled) product? Justify your answer.
(2 Marks)
1. In an experiment where Glacial Acetic Acid (the Carboxylic Acid) and 1-Butanol (the Alcohol) react with concentrated (18M) Sulfuric Acid (H2SO4), then adding water to pass through this mixture and draining the bottom aqueous layer, then doing the same with saturated sodium bicarbonate (NaHCO3) (draining bottom layer), and finally with saturated sodium chloride (NaCl) (draining bottom layer), some Anhydrous Sodium Sulfate (Na2SO4) is added to remove the water from the product. The final product should be Butyl Acetate.
The overall reaction:
Glacial Acetic Acid + 1-Butanol --> Butyl Acetate
or
Chemical Formula of overal reaction:
CH3COOH + C4OH10 --> C6H12O2
a.)
Provide a full mechanism for a possible SN2 side-reaction that may occur under the experimental conditions; include all charges and intermediates. To achieve full marks, use arrows to clearly show bonds forming or breaking between atoms. Vaguely directed arrows will not receive marks. (2.5 Marks)
b.)
Would you expect the side product to be in the purified (i.e. distilled) product? Justify your answer.
(2 Marks)
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