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Question

In the following reaction sequence

 the major product [X] is

The correct answer is

Sure! Let's solve the question step-by-step.

The given reaction sequence involves several steps with specific reagents. Let's break it down:

  1. The first step involves PTSA (p-toluenesulfonic acid), C6H6, and heat. This step likely indicates the formation of an imine between cyclopentanone and pyrrolidine. In the presence of an acid catalyst and heat, the ketone reacts with the amine to form an imine.
  2. The second step uses CHCl3 and NaOH. This combination represents a typical haloform reaction or like the Reimer-Tiemann reaction condition, but here, it could participate in further reactions to introduce a dichlorocarbene. However, here the conditions facilitate oxidation or alpha substitution.
  3. The final step, H3O+, indicates hydrolysis of the formed imine back to a ketone or aldehyde.

Considering these steps, the expected product forms after rearrangement or modification of the imine. On examination of the given options, the correct product as explained follows:

This is the result of the discussed reactions and rearrangements. The imine formation and reversion, facilitated by the reagents provided, lead to the correct major product, as established in organic synthesis sequences.

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Important Questions from Organic Synthesis

  1. For an unambiguous single step synthesis of the following target molecule (TM), the best bond disconnection in its retrosynthetic analysis is
     

  2. The major products X and Y formed in the following reaction sequences are

  3. For the following reaction, the possible product(s) is/are

  4. The reaction(s) that yield(s) X as the major product is (are) 

  5. The major products E and F in the following reaction sequence are 

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