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Question 68

Which statements are True?
A. In Hoffmann bromamide degradation, 4 moles of NaOH and 2 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 Br$$_2$$ and NaOH will give secondary amine.
E. The by-products of Hoffmann degradation are Na$$_2$$CO$$_3$$, NaBr and H$$_2$$O.
Choose the correct answer from the options given below :

Hoffmann bromamide degradation:

$$RCONH_2 + Br_2 + 4NaOH$$ $$\rightarrow$$ $$RNH_2 + 2NaBr + Na_2CO_3 + 2H_2O$$

Analysis of the statements:

For Statement A:

It states that 4 moles of NaOH and 2 moles of $$Br_2$$ are consumed per mole of amide.

From the balanced equation:

$$1 \text{ mole of amide consumes } 1 \text{ mole of } Br_2$$ and $$4 \text{ moles of } NaOH$$

Therefore, $${\text{False}}$$

For Statement B:

Hoffmann bromamide degradation is given by:

$$RCONH_2$$ (primary amides) including alkyl amides such as: $$CH_3CONH_2$$

Hence, $${\text{False}}$$

For Statement C:

The reaction converts a primary amide into a primary amine having one carbon less.

$$RCONH_2$$ $$\rightarrow$$ $$RNH_2$$

Therefore, $${\text{True}}$$

For Statement D:

Secondary amides $$RCONHR'$$ do not undergo Hoffmann degradation to give secondary amines.

The reaction is characteristic of primary amides.

Therefore, $${\text{False}}$$

For Statement E:

From the balanced equation, the by-products are:

$$Na_2CO_3,\; NaBr,\; H_2O$$

Hence, $${\text{True}}$$

Therefore, the true statements are: $${C \text{ and } E}$$

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