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In the Hoffmann rearrangement of primary...

In the Hoffmann rearrangement of primary amides having optically active group with S-configuration, the product amine has

A

R-configuration

B

S-configuration

C

racemic mixture

D

meso-form

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The correct Answer is:
To solve the problem regarding the Hoffmann rearrangement of primary amides with an optically active group having S-configuration, we can break down the process step-by-step. ### Step-by-Step Solution: 1. **Understanding the Starting Material**: - We start with a primary amide of the form R-C(=O)-NH2, where R is an optically active group with S-configuration. 2. **Reagents Used**: - The reagents for the Hoffmann rearrangement include a halogen (like Br2) and a strong base (like NaOH or KOH). 3. **Formation of N-haloamide**: - The primary amide reacts with the halogen to form an N-haloamide. This involves the substitution of the hydrogen atom on the nitrogen with a halogen atom (Br in this case). - The structure now is R-C(=O)-NBr. 4. **Base-Induced Rearrangement**: - The presence of a strong base facilitates the rearrangement. The base abstracts a hydrogen atom from the nitrogen, generating a negative charge on nitrogen. - The R group migrates from the nitrogen to the carbonyl carbon, leading to the formation of an isocyanate intermediate. 5. **Formation of the Product**: - The isocyanate then hydrolyzes in the presence of water (from the base), leading to the formation of a carbamic acid intermediate. - The carbamic acid can then decompose to form the final amine product and carbon dioxide (CO2). 6. **Retention of Configuration**: - Importantly, during the migration of the R group, the stereochemistry of the original optically active group is retained. Since the original configuration was S, the product amine will also have S-configuration. 7. **Conclusion**: - Therefore, the product amine resulting from the Hoffmann rearrangement of a primary amide with an optically active group having S-configuration will also have S-configuration. ### Final Answer: The product amine has S-configuration.

To solve the problem regarding the Hoffmann rearrangement of primary amides with an optically active group having S-configuration, we can break down the process step-by-step. ### Step-by-Step Solution: 1. **Understanding the Starting Material**: - We start with a primary amide of the form R-C(=O)-NH2, where R is an optically active group with S-configuration. 2. **Reagents Used**: ...
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The conversion of an amide into an amine with one carbon atom less by the action of alkaline hydrohalite is known as Hofmann bromamide rearrangement: RCONH_(2) overset(Br_(2)//KOH)toR-NH_(2) The most important feature of the reaction is the arrangement of N–bromamide anion to isocyanate : The product of the reaction Product amine will be :

MODERN PUBLICATION-ORGANIC COMPOUNDS CONTAINING NITROGEN -Competition File (B) MULTIPLE CHOICE QUESTIONS
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  7. The major product of the following reaction is :

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  8. The major product obtained in the following reaction is:

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  9. The major products A and B for the following reaction are :

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  10. The increasing order of reactivity of the following compounds towards ...

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  11. Arrange the following amines in the decreasing order of basicity:

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  12. The increasing basicity order of the following compounds is : (A) CH...

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  14. Which of the following is NOT a Correct method of the preparation of b...

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  15. In the reaction the structure of the product T is :

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  16. The major product of the following reaction is

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  17. Amongst the compounds gives, the one that would form a brilliant color...

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  18. The major product of the reaction is

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  19. In the following reactions, the major product W is

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