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Question

The major product formed in the reaction given below is

The correct answer is

To determine the major product of the given reaction, we first need to understand the reaction conditions and the starting material.

The reaction involves an amine group under diazotization conditions using sodium nitrite (\(NaNO_2\)) and hydrochloric acid (HCl) at low temperatures (0-5°C). This typically results in the conversion of the amine group to a diazonium ion.

Here's a step-by-step breakdown of the reaction process:

  1. The primary amine is converted to a diazonium salt under the reaction conditions.
  2. The bicyclic compound depicted in the reactants has a bridgehead amine. Diazotization in bridged bicyclic systems at the bridgehead often results in rearrangements or unique reactivity due to steric hindrance and strain.
  3. The diazonium group is generally a good leaving group and, under aqueous acidic conditions, can lead to a substitution by \(OH^-\) or water, resulting in an alcohol.

Given the constraints and the typical behavior of diazonium ions, the major product forms as an alcohol. This product is the most feasible one accounting for the reaction's conditions and steric factors.

In conclusion, considering the transformations and typical behavior of diazonium intermediates, the correct product is an alcohol, as shown in the image above.

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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. In the following reaction 

    the major product [X] 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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