-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.
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 45MP
Related questions
Question
100%
Please show all intermediates and label with numbers. Thank you!!
Expert Solution
Step 1
Solution:
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning