Below is the structure of Pentobarbital (Nembutal®), which is a barbiturate sedative. N H Pentobarbital – Nembutal® Two common undergraduate Organic Chemistry reactions are used in the total synthesis: alkylation and nucleophilic acyl substition. Why do they work? 1. NAOET 1. NAOET 2. EtBr 2. Br H,N NH2 HN NH O Amides are more stable than esters. O The CH bonds in diethylmalonate are acidic enough to be deprotonated by ethoxide.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
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Below is the structure of Pentobarbital (Nembutal®), which is a barbiturate sedative.
N
H
Pentobarbital – Nembutal®
Two common undergraduate Organic Chemistry reactions are used in the total
synthesis: alkylation and nucleophilic acyl substition. Why do they work?
1. NAOET
1. NAOET
2. EtBr
2.
Br
H,N NH2
HN
NH
O Amides are more stable than esters.
O The CH bonds in diethylmalonate are acidic enough to be deprotonated by ethoxide.
Transcribed Image Text:Below is the structure of Pentobarbital (Nembutal®), which is a barbiturate sedative. N H Pentobarbital – Nembutal® Two common undergraduate Organic Chemistry reactions are used in the total synthesis: alkylation and nucleophilic acyl substition. Why do they work? 1. NAOET 1. NAOET 2. EtBr 2. Br H,N NH2 HN NH O Amides are more stable than esters. O The CH bonds in diethylmalonate are acidic enough to be deprotonated by ethoxide.
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