EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 30.SE, Problem 30AP
Interpretation Introduction

Interpretation:

A mechanism for the thermal rearrangement of vinyl substituted cyclopropanes in to cyclopentenes identifying the pericyclic process involved is to be proposed.

Concept introduction:

Sigmatropic rearrangements involve the migration of a σ bond present at the end or in the middle of the system across the π electron system from one position to another. They are represented by [m,n] where m and n represents the number of atoms between the bond being broken and the bond being formed in two directions.

If even number of electron pair is involved then thermal reaction occur through antarafacial pathway and photochemical reactions occur through suprafacial pathway.

If odd number of electron pair is involved then thermal reaction occur through suprafacial pathway and photochemical reactions occur through antarafacial pathway.

To propose:

A mechanism for the thermal rearrangement of vinyl substituted cyclopropanes in to cyclopentenes identifying the pericyclic process involved.

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Part II. Given below are the 'H-NMR spectrum at 300 MHz in CDC13 and mass spectrum using electron ionization of compound Brian. The FTIR of the said compound showed a strong peak at 1710 cm"). Determine the following: (a) molecular Formula and Degree of unsaturation of compound Brian (b) Basing on the given H-NMR spectrum tabulate the following (i) chemical shifts (ii) integration, ciii) multiplicity and (iv) interferences made for each signal (c) Draw the structure of compound Brian. ) ΕΙ 43 41 27 71 114 (M+) Hmmm 20 30 40 50 60 70 80 90 100 110 120 1H NMR spectrum 300 MHz in CDCl3 2.0 alle 1.0
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