ORGANIC CHEMISTRY II
PRACTICE PROBLEMS
WEDS. APRIL 7, 2004

1. For each of the following Fischer esterification reactions, draw the reactants and the organic product(s) that would be formed.Name the product(s).If stereoisomers would be formed, draw them and indicate what type they are.

a. acetic acid and propanol

b. benzoic acid and ethanol

c. formic acid and cyclohexanol

d. S-2-methylbutanoic acid and methanol



e. pentanoic acid and 2-butanol

2. Show how each of the following could be prepared by a Fischer esterification reaction. Draw the reactants, name them, and draw the product.

a. butyl propanoate

b. methyl formate

c. ethyl cyclohexanecarboxylate

d. cyclopentyl acetate



3. Draw each of the following esters and give the products that would be formed (name and structure) on acid-catalyzed hydrolysis.

a. isobutyl formate

b. pentyl acetate

c. propyl butanoate

d. cyclohexyl benzoate

e. phenyl pentanoate



Draw the reactants, and draw and name the product of each of the following reactions.

4. 

5.

6.

7. 

8. 

9.



10.

Show what combination of reactants you would use to prepare each of the following compounds from the appropriate acid chloride.Name each compound you use.

11. 3-methylphenyl butanoate

12. N-cyclopropylpentanamide

13. N,N-dimethylbenzamide



14. N-ethyl-3-butenamide

15. cyclopropyl 3,4-dimethylbenzoate

16. tertbutyl 3-cyclopentenecarboxylate