Diethyl n-Butylmalonate Lab Organic Chemistry II Virtual Lab (Guide) Summer 2021, Organic

Diethyl n-Butylmalonate Lab
Organic Chemistry II Virtual Lab (Guide)
Summer 2021, Organic Chemistry II
Objective
To synthesize diethyl n-butylmalonate by the alkylation of diethyl malonate
Chemical equation:
Introduction
Review the introduction in Chapter 42 (page 538).
Mechanism:
As shown above, this experiment involves two important steps. The first step is the formation of an enol by deprotonating diethyl malonate at the alpha carbon. The second step is the alkylation of the enol (which acts as a nucleophile) using 1-bromobutane in an SN2 mechanism.
For an explanation of enol formation with different carbonyls with acidic alpha hydrogen, review this video: https://www.youtube.com/watch?v=WVAv0deX370
For an explanation of the SN2 mechanism, review this video: https://www.youtube.com/watch?v=xoA1zMiCEB4
Experimental Procedure
Use the microscale procedure on page 539 to formulate the steps for the experiment.
Results
Assume the reaction yielded the diethyl n-butylmalonate in 518 mg.
 Use these data to calculate the percent yield. Show all derivations in the result section of your lab report.