Statements on Hoffmann Bromamide Degradation Reaction
Which statements are True ?
A. In Hoffmann bromamide degradation, and are consumed per mole of an amide
B. Hoffmann bromamide reaction is not given by alkyl amides.
C. Primary amines can be synthesized by Hoffmann bromamide degradation.
D. Secondary amide on reaction with and will give secondary amine.
E. The by-products of Hoffmann degradation are , and .
Choose the correct answer from the options given below :
Options
A, C and E only
B, C and D only
C and E only
C, D and E only
Step-by-Step Solution
To determine the correct statements regarding the Hoffmann Bromamide Degradation Reaction, let us analyze the balanced general chemical equation for this reaction:
Now, let us evaluate each statement individually:
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Statement A: "In Hoffmann bromamide degradation, and are consumed per mole of an amide."
- From the stoichiometric coefficients in the balanced reaction, and are consumed per mole of a primary amide.
- Since Statement A mentions , it is Incorrect (False).
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Statement B: "Hoffmann bromamide reaction is not given by alkyl amides."
- Both aliphatic (alkyl) and aromatic (aryl) primary amides undergo the Hoffmann bromamide degradation to yield the corresponding primary amines containing one carbon atom less.
- Therefore, Statement B is Incorrect (False).
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Statement C: "Primary amines can be synthesized by Hoffmann bromamide degradation."
- The reaction specifically converts primary amides () into primary amines ().
- Therefore, Statement C is Correct (True).
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Statement D: "Secondary amide on reaction with and will give secondary amine."
- The reaction mechanism requires two hydrogen atoms on the nitrogen of the amide group () to proceed through the formation of an -bromoamide intermediate followed by base-induced elimination to form an acyl nitrene/isocyanates intermediate ().
- Secondary amides () lack the second acidic hydrogen atom on nitrogen and thus do not undergo this degradation to yield secondary amines.
- Therefore, Statement D is Incorrect (False).
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Statement E: "The by-products of Hoffmann degradation are , and ."
- According to the balanced equation, the side products (by-products) formed alongside the primary amine are sodium carbonate (), sodium bromide (), and water ().
- Therefore, Statement E is Correct (True).
Thus, only statements C and E are true.
Correct Option: C ()