Reaction scheme

Question

can you Devise a reaction scheme to convert propanone into ethyl propanoate.

Answer 1

1st think about the number of carbons in the starting material (propanone or acetone) 3 and ethyl propanoate 5. The acetone has 2 methyl groups attached. There are 2 different ways to get to the product. Remove a methyl group through a haloform reaction and replace with an ethoxide group. To the other methyl, you will take advantage of the fact that it is an alpha carbon and add a methyl to that group. Remember there is always more than 1 route in organic.

Answer 2

Beginning with the propanone (a.k.a. acetone), it needs to be oxidized using a strong oxidizing agent (you could cheat and use PCC, Pyridinium ChloroChromate, as the oxidizing agent) to propanoic acid.

Note: those C's aren't actually capitalized, I just wanted to show how the shortcut name PCC came to be

CH₃--(CO)--CH₃ =(PCC)> CH₃--(CO)--CH₂--OH

Once you've gotten propanoic acid, it needs to react with ethanol to detach the Hydrogen on the far right of the propanoic acid [ CH₃(CO)CH₂OH ] and add the needed ethyl group to form ethyl propanoate.

CH₃--(CO)--CH₂--OH + CH₃--CH₂--OH => CH₃--(CO)--O--CH₂--CH₃ + H₂O

I hope this helps! It has been a bit since I've done Organic Chemistry reactions like this, but this should get you on your way! Message me in the comments if you have any questions, comments, or concerns about my solution and if you'd a depiction of the electron arrows where bonds would break/form in the reactions above; I will do my best later if you ask for it!