ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 23.12, Problem 11P
Interpretation Introduction

Interpretation:

The product obtained in the Claisen rearrangement of C6H5OCH2CH=CHCH3 is to be determined.

Concept introduction:

Allyl phenyl ethers undergo Claisen rearrangement to form o-allyl phenols.

In this type of rearrangement, the allyl group migrates from the oxygen atom in the ring to the carbon atom which is at an ortho position to it.

The transition state formed in the first step of the Claisen rearrangement is similar to that in the Diels-Alder cycloaddition.

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Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)
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