A mixture of all possible monochloro derivatives is formed upon free radical chlorination of 3-methylpentane. When this product mixture is subjected to fractional distillation, the number of distinct fractions obtained is _________

Step-by-step solution

The given compound is 3-methylpentane, CH ₃ -CH ₂ -CH(CH ₃ )-CH ₂ -CH ₃ . The non-equivalent positions for monochlorination and the resulting fractions are: 1) Chlorination at C1 (or C5) gives 1-chloro-3-methylpentane. It has one chiral center at C3, forming a pair of enantiomers. Since enantiomers have identical boiling points, they distill together in 1 fraction. 2) Chlorination at C2 (or C4) gives 2-chloro-3-methylpentane. It has two chiral centers (C2 and C3), forming 4 stereoisomers (2 pairs of enantiomers). S