Alcohols and Ethers - Result Question 4

6. The major product of the following reaction is

(2019 Main, 8 April I)

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(a)

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(b)

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(c)

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(d)

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Show Answer

Answer:

Correct Answer: 6. (b)

Solution:

  1. Ethers are least reactive functional groups. The cleavage of $C-O$ bond in ethers take place under drastic conditions with excess of $H X$.

The major product obtained in the reaction is as follows :

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-357_jpg_height_169_width_562_top_left_y_2315_top_left_x_408.jpg"width="400">

As conc. HBr is in excess. So, reaction will take place at both the substituents.

Mechanism

Step 1: Protonation of ether to form oxonium ion.

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-357_jpg_height_253_width_611_top_left_y_551_top_left_x_1319.jpg"width="400">

Step 2: Attack of nucleophile at the protonated ether.

<img src=“https://imagedelivery.net/YfdZ0yYuJi8R0IouXWrMsA/c55321f0-3a6c-4f0e-a403-fac096bf3900/public"width="400">

Step 3: As $HBr$ is in excess, so, reaction will also take place at alkene.

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/cropped_2024_01_16_b4fdca9f34924034e8d8g-357_jpg_height_190_width_559_top_left_y_1446_top_left_x_1345.jpg"width="400">



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