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Q.

No. of possible monochlorinated product (only structural isomers) of iso-octane 

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answer is 4.

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Detailed Solution

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Iso-octane is 2,2,4-trimethylpentane, its skeletal structure is:

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To count the number of possible monochlorinated structural isomers of iso-octane, consider the distinct types of hydrogen atoms that can be replaced by chlorine.

Types of hydrogens:

  1. On primary carbons (methyl groups): The three types of methyls are:
    • Two equivalent methyls at C-2 (two attached methyl groups on the same carbon),
    • One methyl at C-4,
    • One methyl at C-1 (terminal).
  2. On secondary carbons (CH):
  3. On tertiary carbons (C with three alkyl groups).

Counting distinct positions:

  • Cl substitution on each unique type of hydrogen gives different isomers.

By considering symmetry and positions, the number of distinct monochlorinated structural isomers of iso-octane is 9.

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