Carboxylic Acids and their Derivatives - Result Question 41

Passage

$R \mathrm{CONH}_2$ is converted into $R \mathrm{NH}_2$ by means of Hofmann’s bromamide degradation.

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/snip_images_t2psBpwgwp6INZD6ksgwoSFMTbsI-F8SpUNctVh5ciI_original_fullsize_png.jpg"width="400"/>

In this reaction, $R \mathrm{CONHBr}$ is formed from which this reaction has derived its name. Electron donating group at phenyl activates the reaction. Hofmann’s degradation reaction is an intramolecular reaction.

$(2006,3 \times 4 M=12 M)$

27. What are the constituent amines formed when the mixture of (1) and (2) undergoes Hofmann’s bromamide degradation?

alt text

alt text

Show Answer

Answer:

Correct Answer: 27. (b)

Solution:

The rate determining step of Hofmann’s bromamide reaction is unimolecular rearrangement of bromamide anion (iii) and no cross-products are formed when mixture of amides are taken.

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-396_jpg_height_287_width_767_top_left_y_382_top_left_x_334.jpg"width="400">