Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter D, Problem 9PP
Interpretation Introduction

Interpretation:

The products of the given reaction are to be determined.

Concept introduction:

The mechanism involved in Claisen-cope rearrangement is known to be the 3,3 sigmatropic arrangements as the sigma (σ)-bonded group or atoms gets shifted to a new position with pi (π) bonds.

They are represented by two numbers within brackets, referring to the distance each sigma σ bond has moved. These are concerted reactions, where the positions of all the bonds occur simultaneously once they are initiated by heat.

There are six electrons involved: two σ and four π electrons, contributing to the resonance structure.

The rules for drawing resonance structures are as follows:

Only nonbonding electron pairs and pi electrons can participate in conjugation in the formation of various resonating structures.

The single bonds present in the molecule do not break or form in the resonance structures.

The placement of atoms present in the molecule remains fixed.

The octet of all atoms is completely filled.

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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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