JEE Advanced · 2020 · 27 Sep 2020 · Paper 2 · Alcohols Phenols and Ethers

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An organic compound rotates plane-polarized light. It produces pink color with neutral solution. What is the total number of all the possible isomers for this compound?

Answer: 6

Solution

Given:
  • Molecular formula:
  • Gives test → contains phenolic OH
  • Optically active → contains a chiral center

The compound must be a phenol derivative with a chiral carbon.

Possible structures:
  1. Ortho-hydroxyphenyl ethanol: (2 enantiomers)
  2. Meta-hydroxyphenyl ethanol: (2 enantiomers)
  3. Para-hydroxyphenyl ethanol: (2 enantiomers)

Total = 6 isomers (3 positional isomers × 2 enantiomers each)

JEE Advanced · 2020 · 27 Sep 2020 · Paper 2 · Integer answer

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