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The intermediates formed during the reac...

The intermediates formed during the reaction of `R-overset(O)overset(||)C-NH_(2)` with `Br_(2)` and KOH are :

A

RCONHBr and RNCO

B

RNHCOBr and RNCO

C

RNHBr and RCONHBr

D

`RCONBr_(2)`

Text Solution

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The correct Answer is:
To solve the question regarding the intermediates formed during the reaction of the amide \( R-C(=O)-NH_2 \) with \( Br_2 \) and KOH, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Reaction Type**: The reaction in question is known as the Hofmann bromamide degradation reaction. This reaction involves the conversion of a primary amide into a primary amine with the loss of one carbon atom. **Hint**: Recall that the Hofmann degradation specifically targets primary amides. 2. **Write the Structure of the Amide**: The structure of the amide can be represented as \( R-C(=O)-NH_2 \). **Hint**: Ensure you understand the functional groups present in the amide. 3. **Reaction with Bromine and KOH**: When the amide \( R-C(=O)-NH_2 \) reacts with \( Br_2 \) in the presence of KOH, the bromine will react with the nitrogen atom of the amide. **Hint**: Remember that KOH acts as a base and facilitates the reaction. 4. **Formation of the First Intermediate**: The bromine will attach to the nitrogen, leading to the formation of the intermediate \( R-C(=O)-NBr \) (bromamide). Water is also produced in this step. **Hint**: Look for the addition of bromine to the nitrogen atom. 5. **Elimination Reaction**: The next step involves the elimination of potassium bromide (KBr) and the formation of a new intermediate \( R-C(=O)-N \) (an N-substituted amide). **Hint**: Consider how the elimination of KBr occurs in the presence of KOH. 6. **Rearrangement**: The intermediate undergoes a rearrangement where the nitrogen atom shifts to form a new bond with the alkyl group, resulting in the formation of \( R-N=C=O \) (isocyanate). **Hint**: Rearrangement often involves shifting of groups to stabilize the molecule. 7. **Final Step - Hydrolysis**: Finally, when this isocyanate reacts with water (from the KOH), it hydrolyzes to form the primary amine \( R-NH_2 \) and potassium carbonate \( K_2CO_3 \). **Hint**: Hydrolysis is a common reaction for isocyanates. 8. **Identify the Intermediates**: The two key intermediates formed during this reaction are: - \( R-C(=O)-NBr \) (bromamide) - \( R-N=C=O \) (isocyanate) **Hint**: Make sure to list all intermediates that were formed throughout the reaction. ### Final Answer: The intermediates formed during the reaction of \( R-C(=O)-NH_2 \) with \( Br_2 \) and KOH are: 1. \( R-C(=O)-NBr \) 2. \( R-N=C=O \)

To solve the question regarding the intermediates formed during the reaction of the amide \( R-C(=O)-NH_2 \) with \( Br_2 \) and KOH, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Reaction Type**: The reaction in question is known as the Hofmann bromamide degradation reaction. This reaction involves the conversion of a primary amide into a primary amine with the loss of one carbon atom. **Hint**: Recall that the Hofmann degradation specifically targets primary amides. ...
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