HN O= NH allobarbital This barbiturate can be synthesized in three steps from diethyl malonate: 1 & 2. Diethyl malonate reacts successively with two alkyl bromides in Na+ OEt; 3. The dialkylated intermediate is treated with urea to form the final product. Draw the structures of the two alkyl bromides that must be used to synthesize this barbiturate. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. Sn [1

HN O= NH allobarbital This barbiturate can be synthesized in three steps from diethyl malonate: 1 & 2. Diethyl malonate reacts successively with two alkyl bromides in Na+ OEt; 3. The dialkylated intermediate is treated with urea to form the final product. Draw the structures of the two alkyl bromides that must be used to synthesize this barbiturate. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. Sn [1

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 75AP: One frequently used method for preparing methyl esters is by reaction of carboxylic acids with...

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