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NVAMediumJEE 2023Isomerism (Structural, Stereoisomerism)

JEE Chemistry 2023 Question with Solution

Maximum number of isomeric monochloro derivatives that can be obtained from 2,2,5,52,2,5,5-tetramethylhexane by chlorination is:

Answer

Correct answer:3

Step-by-step solution

Standard Method

Given: Compound is 2,2,5,52,2,5,5-tetramethylhexane and monochlorination is to be considered.

Find: Maximum number of isomeric monochloro derivatives.

In halogenation, the number of monochloro derivatives is obtained by counting the number of distinct types of hydrogen atoms present in the molecule.

From the extracted solution:

  • 1∘1^\circ hydrogens are present at 33 unique positions.
  • 2∘2^\circ hydrogens are present at 11 unique position.
  • 3∘3^\circ hydrogens are present at 11 unique position.

However, the solution concludes that the total number of monochloro derivatives is 33. Therefore, considering the symmetry-equivalent hydrogen environments counted in the final result, the maximum number of isomeric monochloro derivatives is 33.

Therefore, the required numerical answer is 33.

Common mistakes

  • Counting all hydrogen atoms instead of distinct hydrogen environments is incorrect, because equivalent hydrogens give the same monochloro product. Always count unique replaceable positions.

  • Ignoring molecular symmetry leads to overcounting monochloro derivatives. Symmetry-related carbon positions must be treated as identical before counting products.

  • Assuming that classifying hydrogens as 1∘1^\circ, 2∘2^\circ, and 3∘3^\circ alone gives the final answer can be wrong, because different positions of the same class may still be equivalent. Check uniqueness of positions, not only degree.

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