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Question

The major product formed in the following reaction sequence is

The correct answer is

The given reaction sequence involves two main steps. Let's go through them one by one:

Heck Reaction: The first step involves the use of Pd(OAc)2 (Palladium acetate) and Et3N (Triethylamine) in DMSO with heat. This is indicative of a Heck reaction, which is a carbon-carbon bond-forming process between an aryl halide and an alkene. Here, the aryl triflate (OTf) serves as the substrate, reacting with the alkene [CH2=CHOC2H5]. This will result in the formation of a substituted alkene where the aryl group is attached to the terminal carbon of the alkene, replacing the triflate group.

Thermal Cycloaddition Reaction: In the second step, the newly formed product undergoes a cycloaddition with methyl acrylate [CH2=CHCO2Me] under heat. This step likely involves a [4+2] cycloaddition, commonly known as the Diels-Alder reaction, forming a cyclic compound.

To determine the major product, we must recognize that the initial Heck coupling will orient the structure for an optimal Diels-Alder reaction in the next step, resulting in a bicyclic product.

The correct structure resulting from these transformations is illustrated below:

Thus, the major product of this reaction sequence is the one formed by the Heck coupling followed by Diels-Alder cycloaddition, resulting in a bicyclic structure.

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Important Questions from Organic Transformations

  1. The major products X and Y in the following reaction sequence are 

  2. The following conversion is an example of 

  3. The major product formed in the reaction given below is

  4. In the following reaction 

    the major product [X] is

  5. In the following reaction 

    the major product [X] is

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