Ethyl 4-Nitrobenzoate Synthesis Essay

Synthesis of ethyl 4-nitrobenzoate from 4-nitrobenzoic acid  (please see the attached file for more infomation)

1) write a mechanism with electron transfer arrows

2) why must anhydrous ethanol used in this reaction?

3) what will be observed when a reaction is heating at "mild reflux"?

4) To what approximate temperature should the oil bath be heated to attain mild reflux in this experiment?

5) Which compound would you predict will have the larger Rf value(TLC): 4-nitrobenzoic acid or ethyl 4-nitrobenzoate?  Support your choice by illustrating the predominant interaction between the compounds and the silica gel.

6) in the workup phases of the experiment, why is the organic layer washed first with water, and not aqueous NaHCO3? Write the balanced equation to support your choice.

7)why  is the organic layer washed with brine as the final step before drying with sodium sulfate?

8)The Fischer esterification:

 (a)What quantity of acid is used to promote this reaction?

 (b)Why a large quantity of sulfuric acid, compared to 4-nitrobenzoic acid, is used in this experiment?

 (c) what is one disadvantage of using the Fischer esterification method to prepare ester from carboxylic acids? Suggest one alternative synthetic strategy for the preparation of esters that has been devised to overcome the disadvantage

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