Hexamethylbenzene undergoes free-radical chlorination to give one monochlorinated product (C12H17Cl) and four dichlorinated products (C12H16Cl2). These products are easily separated by GC-MS, but the dichlorinated products are difficultto distinguish by their mass spectra. Draw the monochlorinated product and the four dichlorinated products, and explainhow 13C NMR would easily distinguish among these compounds.1

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 67AP: Acidcatalyzed dehydration of 3hydroxy3phenylcyclohexanone leads to an unsaturated ketone. What...
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Hexamethylbenzene undergoes free-radical chlorination to give one monochlorinated product (C12H17Cl) and four dichlorinated products (C12H16Cl2). These products are easily separated by GC-MS, but the dichlorinated products are difficult
to distinguish by their mass spectra. Draw the monochlorinated product and the four dichlorinated products, and explain
how 13C NMR would easily distinguish among these compounds.
1

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