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JEE Main Chemistry question

ChemistryOrganic Chemistry - Some Basic Principles and TechniquesJEE Main

The maximum number of isomers (including stereoisomers) possible on monochlorination of 3-methylpentane, CHCHCH(CH)CHCH, is . [JEE Advanced 2011]

Answer: 8

Solution

3-Methylpentane has four constitutionally distinct substitution positions: (i) C1/C5 (equivalent terminal methyls), giving 1-chloro-3-methylpentane with one stereocentre at C3 (2 stereoisomers); (ii) C2/C4 (equivalent methylenes), giving 2-chloro-3-methylpentane with two stereocentres (4

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Question ID VK-142859