-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.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Please show all intermediates and label with numbers. Thank you!!
Transcribed Image Text:NH
OEt
H2N
1. ΕΙΟ Na"
2 CH3CH2OH
H2N
2. H20
- NH
-OEt
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.
opy aste
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