Benzene and Alkyl Benzene - Result Question 8

12. Match the four starting materials given in Column I with the corresponding reaction schemes provided in Column II and select the correct answer using the code given below the lists.

<img src=“https://imagedelivery.net/YfdZ0yYuJi8R0IouXWrMsA/3694ea2c-428f-43c4-5bec-432db3331f00/public"width="650">

Codes

A B C D
(a) p s q r
(b) r p s q
(c) r s q p
(d) s p r q

(2014 Adv.)

Show Answer

Answer:

Correct Answer: 12. (c)

Solution:

PLAN: This problem can be solved by using the various concepts synthesis of benzene, electrophilic substitution reaction and directive influence of various substituents, including oxidation and reduction.

$\Rightarrow-OH$ and $-NH _2$ are $o / p$-directing groups.

$\Rightarrow N$-acetylation is more favourable than $C$-acylation.

$\Rightarrow N$-sulphonation is more favourable than $C$-sulphonation.

$\Rightarrow NO _2$ is a meta-directing group.

$\Rightarrow H _2 S \cdot NH _3$ reduces only one $NO _2$ group selectively in the presence of two $NO _2$ groups.

Using above concepts the correct sequence of reaction can be written as

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/snip_images_vW8PVsxXqUUPKvmiLEJbWDR7RZd7b0jwwVnhVs_sLFc_original_fullsize_png.jpg"width="600"/>

<img src=“https://temp-public-img-folder.s3.amazonaws.com/sathee.prutor.images/sathee_image/snip_images_2sUaKVIppvUnDsD4_JDl4Lyn7oFbmlkynB4monxyMHk_original_fullsize_png.jpg"width="600"/>

Above reaction proceeds through oxidation, chlorination and amide formation sequentially.

$\therefore A \rightarrow r, B \rightarrow s, C \rightarrow q, D \rightarrow p$

Hence, the correct choice is (c).