Suppose you carried out the following synthesis of 3-methylbutyl ethanoate (isoa

Question

Suppose you carried out the following synthesis of 3-methylbutyl ethanoate (isoamyl acetate):

As the chemical equation shows, 3-methyl-1-butanol (also called isoamyl alcohol or isopentyl alcohol) was mixed with an excess of acetic acid (ethanoic acid by its systematic name) and a trace of sulfuric acid (which serves as a catalyst). This reaction is an equilibrium reaction, so it is expected that not all of the starting materials will be consumed. The equilibrium should lie quite far to the right due to the excess of acetic acid used, but not completely.
After an appropriate length of time, isolation of the desired product from the reaction mixture was begun by adding a volume of 5% aqueous sodium bicarbonate (NaHCO3 has an effective pKa of 7) roughly equal to the volume of the reaction mixture. Bubbling occurred and a mixture consisting of two layers resulted

Suppose you carried out the following synthesis of 3-methylbutyl ethanoate (isoamyl acetate): As the chemical equation shows, 3-methyl-1-butanol (also called isoamyl alcohol or isopentyl alcohol) was mixed with an excess of acetic acid (ethanoic acid by its systematic name) and a trace of sulfuric acid (which serves as a catalyst). This reaction is an equilibrium reaction, so it is expected that not all of the starting materials will be consumed. The equilibrium should lie quite far to the right due to the excess of acetic acid used, but not completely. After an appropriate length of time, isolation of the desired product from the reaction mixture was begun by adding a volume of 5% aqueous sodium bicarbonate (NaHCO3 has an effective pKa of 7) roughly equal to the volume of the reaction mixture. Bubbling occurred and a mixture consisting of two layers resulted???a basic aqueous layer and an organic layer. The layers were separated and the aqueous layer was removed. The addition of aqueous sodium bicarbonate to the layer of organic materials and separation of the layers were repeated twice. Each time the predominantly aqueous layers were removed, they were combined in the same collection flask. The organic layer that remained after the three bicarbonate extractions was dried and then subjected to distillation in order to obtain a pure sample of 3-methylbutyl ethanoate (isoamyl acetate). Choose all the chemical species likely to be present at the end of the reaction but before adding aqueous NaHCO3. Note that the H2SO4 was not consumed (since it is a catalyst), and is thus still available to donate a proton to atoms that can be protonated.

Explanation / Answer

As you have workedup reaction mixture with NaHCO3 ,for several times to isolate the product , the H2SO4 present in the aqueous phase got nuetralised by releasing CO2 gas ,So that there is no acid proton, results no furthur protonation.

2 NaHCO3 + H2SO4 = Na2SO4 + 2CO2 + 2 H2O

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