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NVAEasyJEE 2023Isomerism (Structural, Stereoisomerism)

JEE Chemistry 2023 Question with Solution

The total number of chiral compound/s from the following is _____ .

Set of four chemical structures for chirality identification, including a phenyl-substituted cyclohexane carboxylic acid, a fused aromatic ether ester, a polyhydroxy cyclic compound, and a substituted cyclopropane dicarboxylic acid.
Embedded duplicate overlay handle image from the source editor near the chemical structure figure; not part of the chemistry question content.

Answer

Correct answer:2

Step-by-step solution

Standard Method

Given: Four compounds are shown, and we need to count how many are chiral.

Find: The total number of chiral compounds.

A molecule is chiral if it has at least one chiral carbon attached to four different groups, and the molecule does not have internal symmetry that removes chirality.

Analyze each compound:

  1. Compound 1: The carbon attached to COOH, H, and Ph is chiral. Hence, this compound is chiral.
  2. Compound 2: No carbon atom is bonded to four different groups. Hence, this compound is not chiral.
  3. Compound 3: The molecule has several chiral centers due to multiple asymmetric carbons bearing OH groups. Hence, this compound is chiral.
  4. Compound 4: The cyclopropane carbon atoms are symmetrically substituted, so chirality is absent. Hence, this compound is not chiral.

Therefore, the total number of chiral compounds is 22.

Common mistakes

  • Counting every carbon bearing a substituent as a chiral center. A carbon is chiral only if it is attached to four different groups. Always check all four attachments before declaring chirality.

  • Ignoring symmetry in the molecule. Even if substituted carbons are present, internal symmetry can make the compound achiral. Check for planes or centers of symmetry before counting it as chiral.

  • Assuming that a molecule with multiple OH groups must be achiral or always chiral. The correct approach is to examine each stereogenic center and the overall molecular symmetry together.

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