The steps involved in the given reaction and the reason for the process of cyclopentadiene are to be explained. Concept introduction: According to Huckel’s rule , aromatic compounds contain a planar ring with 4 n + 2 π electrons, where n = 0 , 1 , 2 , 3 , ... An aromatic compound contains conjugated pi bonds and all the atoms in the ring have an unhybridized p orbital The C atom in the aromatic ring is sp 2 hybridized.

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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…

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Question

Chapter 14, Problem 2LGP

Interpretation Introduction

Interpretation:

The steps involved in the given reaction and the reason for the process of cyclopentadiene are to be explained.

Concept introduction:

According to Huckel’s rule, aromatic compounds contain a planar ring with 4n+2π

electrons, where n=0,1,2,3,...

An aromatic compound contains conjugated pi bonds and all the atoms in the ring have an unhybridized p

orbital

The C atom in the aromatic ring is sp² hybridized.

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