Problem 2- Kolbe Reaction

OH

1. NaOH 2. CO2 3. Acid

OH COOH

1 1. Name the function groups in the staring material and product.

2. CO2 is used as a reagent in this reaction. Draw an MO diagram to describe the bonding of CO2. Label all orbitals, ll in the electrons, and indicate which orbitals are the HOMO and the LUMO.

3. In the rst step of this reaction, compound 1 is deprotonated by the NaOH. Draw the product of this reaction. OH 1. NaOH

1 4. Estimate the ratio of 1:1' in solution when this reaction reaches equillibrium.

1'

5. In the next step, 1' reacts with CO2. Based on your answer to question 2, describe the orbitals involved in this reaction. Draw out the CO2 in line form and use curved arrows to show how compound 2 is formed. O 2. CO2 2 1' 6. Compound 2 is further deprotonated. Identify the most acidic proton and draw the product of this deprotonation above. Include any reasonable resonances structure of the product and circle the most stable structure. COO NaOH

7. In the nal step of this reaction, an acid is added to generate the nal product. Suppose HOCl (pKa=7.5) is used. Draw the major product below.

Created by Hanna Key Grinnell College