2. Hexamethylbenzene undergoes free-radical chlorination to give one monochlorinated product (C₁2H17C1) and four dichlorinated products (C12H16C12). These products are easily separated by GC-MS, but the dechlorinated 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. (6 pts) Cl₂/hv Ch/v monochlorinated product dichlorinated products CI

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2. Hexamethylbenzene undergoes free-radical chlorination to give one monochlorinated product (C₁2H17C1) and four
dichlorinated products (C12H16C12). These products are easily separated by GC-MS, but the dechlorinated 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. (6 pts)
Cl₂/hv
Ch/v
monochlorinated product
dichlorinated products
CI
Transcribed Image Text:2. Hexamethylbenzene undergoes free-radical chlorination to give one monochlorinated product (C₁2H17C1) and four dichlorinated products (C12H16C12). These products are easily separated by GC-MS, but the dechlorinated 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. (6 pts) Cl₂/hv Ch/v monochlorinated product dichlorinated products CI
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