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  4. An organic compound ( C 8 H 10 O 2) rotates plane-polarized light. It produces pink color with neutral FeCl 3 solution. What is the total number of all the possible isomers for this compound?

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Q. An organic compound $\left( C _{8} H _{10} O _{2}\right)$ rotates plane-polarized light. It produces pink color with neutral $FeCl _{3}$ solution. What is the total number of all the possible isomers for this compound?

JEE AdvancedJEE Advanced 2020

Solution:

Since given compound produces pink colour with neutral $FeCl _{3}$.
So, it must have at least one $- OH$ group attached to benzene ring.
Also, given compound is optically active, it means it should have a chiral centre, which is only possible when it has - $CH ( OH ) CH _{3}$
So, based on the above observations, compound $\left( C _{8} H _{10} O _{2}\right)$ is expected to possess the following isomeric structures.
image
So, total isomeric structures $= 6$