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Visualized Solution
The Sigma Insight: Amines
Analyzing the Setup Imagine you are in a chemistry lab, and you have a flask containing aniline, a primary aromatic amine
The problem asks us to subject this aniline to a specific sequence of reagents. The first step involves treating aniline with sodium nitrite () and hydrochloric acid () at a chilly temperature of (which is ).
Whenever you see a primary aromatic amine reacting with and at ice-cold temperatures (), your mind should immediately jump to one of the most famous reactions in organic chemistry: Diazotization.
The Master Equation
Diazotization
In the diazotization process, the sodium nitrite and hydrochloric acid react in situ to generate nitrous acid (). This nitrous acid then attacks the amino group () of the aniline. Through a series of protonations and water eliminations, the amino group is transformed into a diazonium group ().
Because we are using , the counter ion is chloride (). Thus, the product formed, Compound A, is Benzene diazonium chloride (). This compound is highly reactive and serves as a versatile synthetic intermediate, acting as a gateway to synthesize a myriad of substituted benzene derivatives.
Final Calculation
The Sandmeyer Reaction
Now, let's move to the second step. Compound A is treated with cuprous cyanide () and heated (). This is a classic example of a nucleophilic aromatic substitution () reaction, specifically known as the Sandmeyer reaction.
The diazonium group () is an exceptionally good leaving group because it leaves as nitrogen gas (), a highly stable and neutral molecule. The departure of nitrogen gas provides a massive thermodynamic driving force for the reaction. As the nitrogen leaves, the cyanide nucleophile () from the cuprous cyanide takes its place on the benzene ring.
This substitution yields Compound B, which is Benzonitrile (). Therefore, our intermediate A is benzene diazonium chloride, and our final product B is benzonitrile. This perfectly matches option (b).
Similar Questions
JEE Main 2021
LEVELJEE Main
Identify correct A, B and C in the reaction sequence given below.
(A)
A = Nitrobenzene, B = m-chloronitrobenzene, C = m-chloroaniline
(B)
A = Nitrobenzene, B = o-chloronitrobenzene, C = o-chlorophenol
(C)
A = Nitrobenzene, B = p-chloronitrobenzene, C = p-chloroaniline
(D)
A = Nitrobenzene, B = p-chloronitrobenzene, C = p-chlorophenol
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LEVELJEE Main
Identify A in the following reaction.
JEE Main 2021
LEVELJEE Main
In the above reactions, products A and B respectively are
(A)
(B)
(C)
(D)
JEE Main 2019
LEVELJEE Main
Benzene diazonium chloride on reaction with aniline in the presence of dilute hydrochloric acid gives
(A)
(B)
(C)
(D)
JEE Main 2020
LEVELJEE Main
Consider the following reactions : The compound [P] is
(A)
(B)
(C)
(D)
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'A' and 'B' in the following reaction are
(A)
(B)
(C)
(D)
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The major products A and B in the following set of reactions are
(A)
(B)
(C)
(D)
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LEVELJEE Main
The major products and formed in the following reaction sequence are
(A)
(B)
(C)
(D)
LEVELJEE Main
Fluorobenzene () can be synthesized in the laboratory
(A)
by heating phenol with HF and KF
(B)
from aniline by diazotisation followed by heating the diazonium salt with
(C)
by direct fluorination of benzene with gas
(D)
by reacting bromobenzene with NaF solution
JEE Main 2021
LEVELJEE Advanced
Which of the following reaction(s) will not give -aminoazobenzene?
(A)
A only
(B)
C only
(C)
B only
(D)
A and B
