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How many distinct monochlorinated products (including stereoisomers) can be obtained by free-radical chlorination of methylcyclobutane when heated with Cl2?
- 4
- 5
- 6
- 7
Correct answer: 6
Solution
Methylcyclobutane has distinct H sets: CH3 (primary, 1 product), C1-H (tertiary, 1 product), C2/C4 axial/equatorial positions (give cis and trans 1-methyl-2-chlorocyclobutane = 2 stereoisomers), and C3 (gives 1-methyl-3-chlorocyclobutane with cis/trans = 2 stereoisomers). Total = 1 + 1 + 2 + 2 = 6 distinct products.
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