JEE Challenger
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Statements on Hoffmann Bromamide Degradation Reaction

Which statements are True ?

A. In Hoffmann bromamide degradation, 4 moles of NaOH4\text{ moles of NaOH} and 2 moles of Br22\text{ moles of Br}_2 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 Br2\text{Br}_2 and NaOH\text{NaOH} will give secondary amine.

E. The by-products of Hoffmann degradation are Na2CO3\text{Na}_2\text{CO}_3, NaBr\text{NaBr} and H2O\text{H}_2\text{O}.

Choose the correct answer from the options given below :

Options

A

A, C and E only

B

B, C and D only

C

C and E only

Correct
D

C, D and E only

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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:

R-CONH2+Br2+4NaOHR-NH2+Na2CO3+2NaBr+2H2O\text{R-CONH}_2 + \text{Br}_2 + 4\text{NaOH} \rightarrow \text{R-NH}_2 + \text{Na}_2\text{CO}_3 + 2\text{NaBr} + 2\text{H}_2\text{O}

Now, let us evaluate each statement individually:

  1. Statement A: "In Hoffmann bromamide degradation, 4 moles of NaOH4\text{ moles of NaOH} and 2 moles of Br22\text{ moles of Br}_2 are consumed per mole of an amide."

    • From the stoichiometric coefficients in the balanced reaction, 1 mole of Br21\text{ mole of Br}_2 and 4 moles of NaOH4\text{ moles of NaOH} are consumed per mole of a primary amide.
    • Since Statement A mentions 2 moles of Br22\text{ moles of Br}_2, it is Incorrect (False).
  2. 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).
  3. Statement C: "Primary amines can be synthesized by Hoffmann bromamide degradation."

    • The reaction specifically converts primary amides (R-CONH2\text{R-CONH}_2) into primary amines (R-NH2\text{R-NH}_2).
    • Therefore, Statement C is Correct (True).
  4. Statement D: "Secondary amide on reaction with Br2\text{Br}_2 and NaOH\text{NaOH} will give secondary amine."

    • The reaction mechanism requires two hydrogen atoms on the nitrogen of the amide group (-CONH2\text{-CONH}_2) to proceed through the formation of an NN-bromoamide intermediate followed by base-induced elimination to form an acyl nitrene/isocyanates intermediate (R-N=C=O\text{R-N=C=O}).
    • Secondary amides (R-CO-NHR’\text{R-CO-NHR'}) 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).
  5. Statement E: "The by-products of Hoffmann degradation are Na2CO3\text{Na}_2\text{CO}_3, NaBr\text{NaBr} and H2O\text{H}_2\text{O}."

    • According to the balanced equation, the side products (by-products) formed alongside the primary amine are sodium carbonate (Na2CO3\text{Na}_2\text{CO}_3), sodium bromide (NaBr\text{NaBr}), and water (H2O\text{H}_2\text{O}).
    • Therefore, Statement E is Correct (True).

Thus, only statements C and E are true.

Correct Option: C (C and E only\text{C and E only})

Statements on Hoffmann Bromamide Degradation Reaction | Chemistry PYQ Solution - JEE Challenger