ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 23, Problem 6PP
Interpretation Introduction

Interpretation:

The structure of products of the given reactions is to be determined.

Concept introduction:

The compound pbenzoquinone is ubiquinone (terpene-modified quinones) obtained by the oxidation of hydroquinone. The oxidation may lead to the removal of two electrons and two protons from the hydroquinone or the loss of two hydrogen atoms.

The compound 1,4Naphthoquinone is a naphthalene derivative and is an important chemical found in the vitamin K1. It acts as a dienophile in the Diels-Alder reaction.

Diels-Alder reaction is a reaction that takes place between two organic compounds, such that one is a conjugated diene and the other is a substituted alkene. It is a key reaction in the synthesis of many complex compounds such as, cortisone and cholesterol.

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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1
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