The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the final product. Show the mechanism of addition and the structure of the final un-charged addition product.

The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the final product. Show the mechanism of addition and the structure of the final un-charged addition product.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter27: Amines

Section: Chapter Questions

Problem 5E

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