spectra of his unknown ester in E6. He claims that he carried out all of the necessary steps for the workup of his Fischer esterification, and yet the spectra does not look how he anticipated. Looking through his notebook, you notice some last minute changes to the procedure. He mistakenly used half the volume of acetic acid and refluxed the reaction for 30 min. He neutralized the remaining acid with Na2CO3
and extracted with MTBE. After washing his organic layer with aq. 10% Na2CO3 twice and brine once, he dried the organic phase with anhydrous magnesium sulfate. Next, Jack Johnson removed the MTBE solvent by careful evaporation until the mass was constant. Consider the purpose of each step in the workup, identify Jack's key mistake, explain what happened as a result, and how this would affect the IR spectra (be specific about which peak/s are unexpectedly present and/or absent?)
Jack's most important mistake was that he_______
The reaction was not complete
Equilibrium does not favor the products
Residual acetic acid was not removed
aqueous impurities was not removed
residulal alcohol was not removed
As a result _______ and the IR spectra will show
Show signals from both starting materials
show signals from residual water
show signals from the starting acetic acid
show signals from the starting alcohol
not be affected
