Identify [A], [B], and [C], respectively in the following reaction sequence :
![Reaction sequence showing diazotization of aromatic amine to benzene diazonium chloride, then reaction with KI, followed by 2Na in dry ether to form final product [C].](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/lhhFULZLvjcfExfGkDBXB.png)
- A
![Option showing [A] as aniline, [B] as chlorobenzene, and [C] as iodobenzene on benzene rings with labels.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/lApVgHOFV9E3BWrMA4hSS.png)
- B
![Option showing [A] as aniline, [B] as chlorobenzene, and [C] as benzene without substituent on aromatic ring.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/gcZ-tcQ5MEWavot0xIt02.png)
- C
![Option showing [A] as aniline, [B] as iodobenzene, and [C] as biphenyl with two benzene rings joined directly.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/g-voJZfUrp1VNCEjCxKwd.png)
- D
![Option showing [A] as nitrobenzene, [B] as iodobenzene, and [C] as biphenyl with two benzene rings joined directly.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/CWGL4pmvsUlgOSaPyf6P8.png)
Identify [A], [B], and [C], respectively in the following reaction sequence :
![Reaction sequence showing diazotization of aromatic amine to benzene diazonium chloride, then reaction with KI, followed by 2Na in dry ether to form final product [C].](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/lhhFULZLvjcfExfGkDBXB.png)
![Option showing [A] as aniline, [B] as chlorobenzene, and [C] as iodobenzene on benzene rings with labels.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/lApVgHOFV9E3BWrMA4hSS.png)
![Option showing [A] as aniline, [B] as chlorobenzene, and [C] as benzene without substituent on aromatic ring.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/gcZ-tcQ5MEWavot0xIt02.png)
![Option showing [A] as aniline, [B] as iodobenzene, and [C] as biphenyl with two benzene rings joined directly.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/g-voJZfUrp1VNCEjCxKwd.png)
![Option showing [A] as nitrobenzene, [B] as iodobenzene, and [C] as biphenyl with two benzene rings joined directly.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/CWGL4pmvsUlgOSaPyf6P8.png)
Correct answer:C
Standard Method
Given: The reaction sequence involves treatment of [A] with and at , followed by reaction with , and then with in dry ether.
Find: Identify [A], [B], and [C].
The first step is diazotization. An aromatic primary amine forms a diazonium salt under these conditions, so [A] must be aniline, .
The diazonium salt then reacts with . This replaces the diazonium group by iodine, so [B] is iodobenzene, .
In the final step, aryl halide with in dry ether undergoes coupling to form biphenyl. Therefore [C] is biphenyl, .
![Solution diagram showing aniline as [A], diazonium chloride intermediate, iodobenzene as [B], and biphenyl as [C] formed using 2Na in dry ether.](https://cdn.jeeify.com/questions/JEE_MAIN_2025_APR_03_S1/1202504030162/5MGOBJxN0irUUkuZNwcXJ.png)
Therefore, the correct option is C.
Stepwise Identification
Given: Recognize the reactions involved: diazotization, Sandmeyer reaction, and coupling reaction.
Find: The identities of [A], [B], and [C].
Step 1: The first reaction involves the treatment of [A] with and at .
This is a typical diazotization reaction where an aromatic amine (aniline) is converted into a diazonium salt. Thus, [A] is aniline, .
Step 2: The diazonium salt formed reacts with .
This is a Sandmeyer reaction where the diazonium group is replaced by iodide to form an iodobenzene compound. Hence, [B] is iodobenzene, .
Step 3: The compound undergoes a reaction with in dry ether.
This reaction is a typical Wurtz reaction where iodobenzene reacts with sodium to form biphenyl. Therefore, [C] is biphenyl, .
Thus, the correct answer is: Aniline ([A]) Iodobenzene ([B]) Biphenyl ([C]). Hence, the correct option is C.
Mistake: Identifying [A] as nitrobenzene instead of aniline. This is wrong because diazotization with at low temperature requires a primary aromatic amine. Do instead: choose aniline as the starting compound.
Mistake: Assuming gives chlorobenzene or leaves the diazonium salt unchanged. This is wrong because iodide replaces the diazonium group to form iodobenzene. Do instead: recognize the substitution product as aryl iodide.
Mistake: Not recognizing the final sodium-dry ether step as coupling. This is wrong because aryl halides under these conditions form a biaryl product. Do instead: identify [C] as biphenyl, not benzene or a mono-substituted ring.
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