JEE Challenger
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Ozonolysis and Reductive Ring Formation of Methyl Indene

In the following sequence of reactions, determine the identity of the product S\mathbf{S}:

Question Diagram 1

Options

A
Option A Diagram 1
Correct
B
Option B Diagram 1
C
Option C Diagram 1
D
Option D Diagram 1

Step-by-Step Solution

To determine the identity of the product S\mathbf{S}, we trace the reaction sequence step by step:

Step 1: Ozonolysis of the Alkene Derivative (Formation of R)

The starting material is a substituted indene derivative containing a fused benzene ring and a cyclopentene ring with a methyl group (−CH3-\text{CH}_3) at the top-left position of the benzene ring.

Under reductive ozonolysis conditions:

  1. O3\text{O}_3 selectively cleaves the more electron-rich, non-aromatic carbon-carbon double bond (−CH=CH−-\text{CH}=\text{CH}-) in the five-membered ring.
  2. Subsequent reduction with Zn/H2O\text{Zn} / \text{H}_2\text{O} yields a dicarbonyl compound R\mathbf{R}, containing:
    • An aromatic aldehyde group (−CHO-\text{CHO}) attached directly to the benzene ring.
    • An aliphatic aldehyde group (−CH2−CHO-\text{CH}_2-\text{CHO}) attached to the adjacent position of the benzene ring.

The structure of R\mathbf{R} is 2-(2-oxoethyl)benzaldehyde with the −CH3-\text{CH}_3 substituent intact at the position meta to the −CH2CHO-\text{CH}_2\text{CHO} group and para to the direct −CHO-\text{CHO} group (top-left).


Step 2: Reaction with Ammonia (NH3\text{NH}_3) (Formation of S)

The 1,5-dicarbonyl compound R\mathbf{R} undergoes nucleophilic attack by ammonia (NH3\text{NH}_3):

  1. The lone pair on ammonia attacks one of the aldehyde carbonyl carbons, followed by intramolecular attack on the second aldehyde carbonyl carbon to form a six-membered cyclic intermediate.
  2. Subsequent dehydration (loss of two molecules of H2O\text{H}_2\text{O}) and aromatization results in the formation of a stable isoquinoline ring system.

Since the cyclization of 2-(2-oxoethyl)benzaldehyde with NH3\text{NH}_3 yields isoquinoline (where the nitrogen atom is at position 22, not at position 11 as in quinoline), the resulting product S\mathbf{S} is 7-methylisoquinoline.


Conclusion:

Comparing with the given options:

  • (A) correctly shows the isoquinoline ring (with nitrogen at position 22) and the methyl group located at position 77 (top-left).

Therefore, the correct option is (A).