JEE Main Chemistry question

ChemistryOrganic Chemistry - Some Basic Principles and TechniquesJEE Main

How many chiral monochlorinated products are obtained from 2-methylpentane, (CH)CH–CH–CH–CH?

Answer: 3

Solution

Substitution at C1 (or the equivalent branch methyl) gives 1-chloro-2-methylpentane, with a new stereocentre at C2 (four different groups) — chiral. Substitution at C2 gives 2-chloro-2-methylpentane, whose C2 bears two identical methyls — achiral. Substitution at C3 gives

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Question ID VK-142910