Question Details

The reagent ‘R’ in the given sequence of chemical reaction is :

Options

A

H2O

B

CH3CH2OH

C

HI

D

CuCN/KCN

Show Answer

Correct Answer :

Option B

CH3CH2OH

CH₃CH₂OH

Solution :

The correct answer is: CH3CH2OH (Ethanol)

Let us analyze the reaction sequence shown in the image step by step.

Step 1: Identify the Starting Material
The starting compound is 2,4,6-tribromoanline — a benzene ring bearing an −NH2 (amine) group and three bromine (Br) substituents at positions 2, 4, and 6.

Step 2: First Reaction — Diazotization
The amine is treated with NaNO2 / HCl at 0–5°C. This is a classic diazotization reaction. The primary aromatic amine (−NH2) reacts with nitrous acid (HNO2, generated in situ from NaNO2 and HCl) at low temperature to form a diazonium salt (−N2+ Cl).

So the intermediate product is 2,4,6-tribromobenzenediazonium chloride, as clearly shown in the image with the N2+ Cl group attached to the ring.

Step 3: Second Reaction — Treatment with Reagent 'R'
The diazonium salt is then treated with the unknown reagent R, and the final product shown in the image is 1,3,5-tribromobenzene ��� a benzene ring with only three bromine atoms and no nitrogen-containing group. The −N2+ Cl group has been replaced by a hydrogen atom (−H).

Step 4: Identify the Reaction Type
The replacement of the diazonium group (−N2+) by a hydrogen atom (−H) is known as deamination or reductive de-diazotization. In this reaction, nitrogen gas (N2) is evolved, and a C−H bond is formed where the C−N2+ bond existed.

Step 5: Which Reagent Achieves This?
The standard reagent used to replace a diazonium group with hydrogen is ethanol (CH3CH2OH). When a diazonium salt is warmed with ethanol, the following occurs:

Ar−N2+ Cl + CH3CH2OH → Ar−H + N2↑ + CH3CHO + HCl

Ethanol acts as a reducing agent (specifically, a hydride source). It donates a hydrogen atom to the aryl ring, replacing the diazonium group. In the process, ethanol itself gets oxidized to acetaldehyde (CH3CHO), and nitrogen gas is released.

Why not the other options?

H2O — Water with a diazonium salt would give a phenol (Ar−OH), not Ar−H.
HI — While HI can also replace −N2+ with −H via a radical pathway, the classical and most widely recognized reagent for this transformation in standard organic chemistry is ethanol.
CuCN/KCN — This is a Sandmeyer reaction reagent that would replace −N2+ with −CN (a nitrile group), not −H.

Therefore, the reagent R is CH3CH2OH (Ethanol).

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