Esterification

You will make isopentyl acetate (banana oil) according to the instructions in your lab text on page 93. Obtain the IR and nmr spectra of the product.

Answer the following questions as part of your report:

1) a) If the Keq for the esterification of acetic acid with isopentyl alcohol is 3.0, what is the maximum amount of isopentyl acetate that can be recovered at equilibrium if a 1:1 mole ratio of acid:alcohol is used?

b) If a 1:5 mole ratio is used?

c) 5:1 mole ratio?

2) What role does sulfuric acid play in this reaction? Explain; show equations.

3) Tell what effect doubling the concentration of sulfuric acid would have on the yield of the ester.

4) Why were the contents of the round bottom flask after reflux poured into 10 mL of water?

5) Why do we wash the ester with sodium carbonate solution?

6) Why would solid NaOH not be a good drying agent for the ester?

7) How would you distinguish between the nmr spectra of methyl benzoate and phenyl acetate?