HydrocarbonshardNUMERICAL

Isopentane (2-methylbutane) is subjected to free radical chlorination (). How many structurally distHydrocarbons Chemistry Question

Question

Isopentane (2-methylbutane) is subjected to free radical chlorination ($Cl_2/h u$). How many structurally distinct monochlorinated products (excluding stereoisomers) can be formed?

Answer: 4

💡 Solution & Explanation

The structure of 2-methylbutane is $CH_3-CH(CH_3)-CH_2-CH_3$. It contains four distinct types of hydrogen environments: 1) the primary hydrogens on C1, 2) the tertiary hydrogen on C2, 3) the secondary hydrogens on C3, and 4) the primary hydrogens on C4. Substitution at any of these positions leads to a unique structural isomer: 1-chloro-2-methylbutane, 2-chloro-2-methylbutane, 3-chloro-2-methylbutane, and 1-chloro-3-methylbutane. Total = 4.

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