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Reaction of RCONH(2) with a mixture of B...

Reaction of `RCONH_(2)` with a mixture of `Br_(2)` and `KOH` gives `RNH_(2)` as the main product. The intermediates involved in the reaction are:

A

`R-overset(OH)overset(|)(C)=N-Br`

B

`R-NHBr`

C

`R-N=C=O`

D

Text Solution

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The correct Answer is:
To solve the problem, we need to analyze the reaction of an amide (RCONH₂) with a mixture of bromine (Br₂) and potassium hydroxide (KOH) to determine the intermediates involved in the process. The main product of this reaction is an amine (RNH₂). ### Step-by-Step Solution: 1. **Identify the Reaction Type**: The reaction described is known as the Hofmann rearrangement, which involves the conversion of an amide to an amine with the loss of one carbon atom. 2. **Starting Material**: The starting material is an amide, RCONH₂. In the presence of Br₂ and KOH, the amide undergoes a rearrangement. 3. **Formation of an Intermediate**: The first step involves the formation of an intermediate. When RCONH₂ reacts with Br₂ in a basic medium (KOH), the bromine will react with the nitrogen atom of the amide. This leads to the formation of an N-bromoamide (RCONHBr). 4. **Formation of Carbamic Acid**: The N-bromoamide can further react in the presence of water (from the KOH solution) to form an intermediate known as carbamic acid (R-NHCOOH). This is where the nitrogen is bonded to a carbonyl group (C=O) and has a hydroxyl group (OH). 5. **Final Product Formation**: The carbamic acid can then decompose to yield the final product, which is an amine (RNH₂) and carbon dioxide (CO₂). The nitrogen atom in the carbamic acid loses a carbon atom during this rearrangement, resulting in the formation of the amine. 6. **Identify the Intermediates**: Based on the steps above, the intermediates involved in the reaction are: - N-bromoamide (RCONHBr) - Carbamic acid (R-NHCOOH) However, the question specifically asks for the intermediates involved, and among the options given, the correct intermediate that fits the description is R-N-C-O (which represents the carbamic acid structure). ### Conclusion: The main intermediate involved in the reaction is **R-N-C-O**, which corresponds to the carbamic acid formed during the reaction. ### Final Answer: The correct answer is **C: R-N-C-O**. ---
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