-NH -OEt H2N 1. EtO Na* 2 CH,CH2OH 2. H,0 - NH -OEt H,N Barbiturates are prepared by treating a derivative of diethyl malonate with urea in the presence of sodium ethoxide as catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea. Write a detailed mechanism for this reaction (shown above) which proceeds in 6 steps, including proton transfer steps. Then draw Intermediate 1 in the window provided. The mechanism is detailed as follows: Step 1: Deprotonation of urea to yield intermediate 1. Step 2: Nucleophilic attack to yield intermediate 2. Step 3: Collapse of tetrahedral center in intermediate 2 to yield intermediate 3. Step 4: Deprotonation to yield intermediate 4. Step 5: Intramolecular nucleophilic attack to yield charged intermediate 5. Step 6: Collapse of tetrahedral center in intermediate 5 to yield to product. • You do not have to consider stereochemistry. • In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na*, r, in your answer. • Do not draw organic or inorganic by-products.

-NH -OEt H2N 1. EtO Na* 2 CH,CH2OH 2. H,0 - NH -OEt H,N Barbiturates are prepared by treating a derivative of diethyl malonate with urea in the presence of sodium ethoxide as catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate and urea. Write a detailed mechanism for this reaction (shown above) which proceeds in 6 steps, including proton transfer steps. Then draw Intermediate 1 in the window provided. The mechanism is detailed as follows: Step 1: Deprotonation of urea to yield intermediate 1. Step 2: Nucleophilic attack to yield intermediate 2. Step 3: Collapse of tetrahedral center in intermediate 2 to yield intermediate 3. Step 4: Deprotonation to yield intermediate 4. Step 5: Intramolecular nucleophilic attack to yield charged intermediate 5. Step 6: Collapse of tetrahedral center in intermediate 5 to yield to product. • You do not have to consider stereochemistry. • In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na*, r, in your answer. • Do not draw organic or inorganic by-products.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.64P

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