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A: In Hofmann's bromamide degradation am...

A: In Hofmann's bromamide degradation amines formed containing one carbon atom less than carbon atoms present in amide.
R: This reaction occurs through the formation of nitrine intermediate

A

If both Assertion & Reason are true and the reason is the correct explanation of the assertion, then mark (1).

B

If both Assertion & Reason are true but the reason is not the correct explanation of the assertion, then mark (2)

C

If Assertion is true statement but Reason is false, then mark (3)

D

If both Assertion and Reason are false statements, then mark (4)

Text Solution

AI Generated Solution

The correct Answer is:
### Step-by-Step Solution: 1. **Understanding the Reaction**: - The Hofmann bromamide degradation reaction involves the conversion of a primary amide into a primary amine. The key feature of this reaction is that the amine produced contains one carbon atom less than the original amide. 2. **Chemical Reaction**: - The reaction can be represented as follows: \[ R-CO-NH_2 + Br_2 + KOH \rightarrow R-NH_2 + K_2CO_3 + KBr + H_2O \] - Here, \(R-CO-NH_2\) is the primary amide, and \(R-NH_2\) is the primary amine formed. 3. **Mechanism of the Reaction**: - The mechanism begins with the reaction of the primary amide with bromine (\(Br_2\)) in the presence of potassium hydroxide (\(KOH\)). - This leads to the formation of an intermediate called acyl nitrene. 4. **Formation of Acyl Nitrene**: - The primary amide reacts to form a brominated intermediate: \[ R-C(=O)-NH-Br \] - In a basic medium, the base abstracts a proton from the nitrogen, leading to the formation of acyl nitrene: \[ R-C(=O)-N^-(Br) \] - The bromine leaves as bromide ion (\(Br^-\)), resulting in the acyl nitrene intermediate. 5. **Rearrangement**: - The acyl nitrene undergoes rearrangement to form an isocyanate: \[ R-C(=O)-N=C=O \] - This rearrangement is crucial as it leads to the formation of the product. 6. **Hydrolysis**: - The isocyanate undergoes hydrolysis in the presence of \(KOH\) to yield the primary amine: \[ R-NH_2 \] - This primary amine has one carbon atom less than the original amide. 7. **Conclusion**: - The assertion is true: in Hofmann's bromamide degradation, the amine formed contains one carbon atom less than the carbon atoms present in the amide. - The reason is also true: the reaction occurs through the formation of a nitrene intermediate (specifically, acyl nitrene). - However, the reason does not correctly explain the assertion. ### Final Answer: Both the assertion and the reason are true, but the reason is not the correct explanation for the assertion. Therefore, the correct option is option 2. ---
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