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EstersandAlcohols-AlternativeAssignment-Lab2.pdf

Name:______________________ Date: _________________

Experiment: Fisher Esterification

Watch the following video: https://www.youtube.com/watch?v=lJLP2bcXDqY

1. Describe the Fisher Esterification synthesis.

2. Show a reaction scheme for the synthesis of methyl salicylate from salycilic acid and

methanol.

3. Provide a step-by-step reaction mechanism for the synthesis of the target product.

4. Calculate the theoretical yield of your target product. Show calculations. You need to

used the grams mentioned in the video for your calculations.

5. Which compound is the limiting reagent? Show calculations.

6. Calculate the percent yield of the target product. Show calculations.

7. Provide a detailed experimental procedure for the synthesis of methyl salicylate from

salycilic acid and methanol.

8. In the work up of the reaction mixture, what is the purpose of (a) washing the organic

layer with sodium bicarbonate solution, (b) simple distillation?

9. What is the boiling point of methyl salicylate?

10. Methyl salicylate is known as the oil of ________________.

11. Why do you need an acid as a catalyst if you already have a carboxylic acid as one of the

reagents for the Fisher esterification synthesis? Show any reaction scheme and/or

chemical structures to support your detailed explanation.

12. Describe the expected IR data for your reaction product. 8. How could you synthesize

propyl acetate (pear scent) using the Fisher esterification synthesis? Propose a reaction

scheme.

13. Ethyl propanoate (pineapple scent) can be prepared by the reaction of ethanol with

_____________using sulfuric acid as a catalyst by the use of the Fisher esterification

synthesis. Propose two different experimental methods that could be done to increase the

percent yield of the product? Provide a detailed explanation.

14. How could you synthesize an ester that has the scent of bananas using the Fisher

Esterification?