Question

Ö 11-11: Dieckmann Reaction For this assignment, the target compound that you should synthesize is 2-oxo-cyclohexane carboxylic acid methyl ester.This is an intramolecular carbonyl addition variation. Examine the product and determine which ester is the nucleophile and which is the electrophile. Keep in mind the mechanism and that you need to acidify the intermediate in order to isolate a neutral product. Synthesis Procedures 1. Start Virtual ChemLab and select Dieckmann Reactionfrom the list of assignments ontbe whiteboard. After entering the synthesis laboratory, use the available reagents on the stockroom shelf, identify the appropriate starting materials required to synthesize the target compound and add them to the round bottom flask. Select the appropriate solvent and drag the flask to the Stir Plate on the lab bench. 2. The round bottom flask containing the starting materials should now be on the stir plate, and the contents of the flask should be visible on the chalkboard. From the group of reagents found on the lab bench, select the correct reagent to synthesize the target compound and add it to the flask on the stir plate. Now attach the heater, condenser, and N2 gas to the round bottom flask so the reaction mixture can be heated. 3. Start the reaction by clicking on the Stir button on the front of the stir plate. You should be able to observe the reaction mixture stirring in the flask. Monitor the progress of the reaction using TLC measurements as necessary until the product has formed and the starting materials have been consumed. You can advance the laboratory time using the clock on the wall. With the electronic lab book open (click on the lab book on the stockroom counter), you can also save your TLC plates by clicking Save on the TLC window. 4. When the reaction is complete, “workup” your reaction by first dragging and dropping the separatory funnel on the flask and then adding H20 to the funnel. Extract the organic layer in the funnel by clicking on the top layer and dragging it to the cork ring on the lab bench. Your target compound should now be in this flask. List the starting materials, solvent, reagent, and products formed: Starting Materials: 1,7-Dimethyl-heptanedioate Solvent: Diethyl ether Reagent: sodium methoxide Products: 3-oxo-cyclohexane carboxylic acid methyl ester How long did it take to finish the reaction? Around 1 hour What are the TLC values (R) for (a) Starting Materials: 0.6 (b) Products: 0.5 Write a mechanism for this reaction:

I need help with questions 5, 6, & 7. The FTIR and NMR is provided. I also need help creating a reaction mechanism using the following:  

Starting material: 1,7-Dimethyl-heptanedioate

Solvent: Diethyl ether

Reagent: sodium methoxide

Product: 3-oxo-cyclohexane carboxylic acid methyl ester

THANK YOU!!!!!