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Animated Solution for Chemistry - Organic Chemistry: In the chemical reaction, compounds A and B respectively are

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Visualized Solution

The Sigma Insight: Amines

Solution Diagram

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

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