The major product formed in the following reaction is

F1 Savita Teaching 24-4-23 D28

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CSIR-UGC (NET) Chemical Science: Held on (15 Dec 2019)
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  1. F1 Savita Teaching 24-4-23 D29
  2. F1 Savita Teaching 24-4-23 D30
  3. F1 Savita Teaching 24-4-23 D31
  4. F1 Savita Teaching 24-4-23 D32

Answer (Detailed Solution Below)

Option 1 : F1 Savita Teaching 24-4-23 D29
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Detailed Solution

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Concept:

→ The reaction you described is a bromination reaction, where 3-methylthiophene is reacted with N-bromosuccinimide (NBS) in the presence of a radical initiator such as (PhCOO)2 and benzene (C6H6) under heat.

→ The reaction mechanism involves the formation of a bromine radical from NBS, which reacts with the 3-methylthiophene molecule to form a thiophene radical intermediate.

→ This radical intermediate then reacts with molecular bromine to form a more stable intermediate. This intermediate then undergoes rearrangement to form 3-(bromomethyl)thiophene as the major product.

Explanation:

The reaction can be summarized as follows:

Step 1: Formation of a bromine radical from NBS:

NBS + heat → Br• + NsH

Step 2Reaction of the bromine radical with 3-methylthiophene to form a thiophene radical intermediate:

Br• + 3-methylthiophene → 3-methylthiophene radical

Step 3: Reaction of the thiophene radical intermediate with molecular bromine to form a more stable intermediate:

3-methylthiophene radical + Br2F1 Savita Teaching 24-4-23 D33

Step 4: Rearrangement of the intermediate to form 3-(bromomethyl)thiophene as the major product:

F1 Savita Teaching 24-4-23 D33F1 Savita Teaching 24-4-23 D34 

Conclusion: Therefore, the major product formed in the reaction of 3-methylthiophene in the presence of NBS, (PhCOO)2, C6H6, heat is 3-(bromomethyl)thiophene. Therefore, the correct answer is option 1 .

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