Animated Solution for Chemistry - Organic Chemistry: Consider the above chemical reaction and identify product "A"
Select Answer:
Visualized Solution
\text{Reaction Sequence}
R−C≡NH2​O/H+​AH2​O/H+,Δ​R−COOH
\text{Hydrolysis of Nitriles}
\text{Nitriles undergo hydrolysis in acidic or basic medium.}
\text{Partial Hydrolysis}
R−C≡NH2​O/H+​R−CONH2​ (Amide)
\text{Identifying Product A}
\text{Product A is Cyclohexanecarboxamide.}
\text{Complete Hydrolysis}
R−CONH2​H2​O/H+,Δ​R−COOH+NH3​
\text{The Way Forward}
\text{What if we used } LiAlH_4 \text{ instead?}
00:00 / 00:00
The Sigma Insight: Carbonyl Compounds
Solution Diagram
Analyzing the Setup
Imagine you are a molecular architect, and your starting material is 1-cyanocyclohexane
We are presented with a two-step reaction sequence. Our primary objective is to deduce the identity of the intermediate product, labeled as "A".
The reaction begins with the treatment of our starting material with water in an acidic medium (H2​O/H+). This is a classic condition for the hydrolysis of nitriles.
The Master Equation
Hydrolysis of Nitriles
When nitriles (−C≡N) are subjected to aqueous acid, they don't just instantly turn into carboxylic acids. The process is beautifully staged.
The first stage is partial hydrolysis. Without the application of external heat, the water molecule adds across the carbon-nitrogen triple bond. This breaks the π-bonds and transforms the nitrile group into an amide group (−CONH2​).
R−C≡NH2​O/H+​R−CONH2​
Identifying Product A
Applying this logic to our specific molecule, the cyanide group attached to the cyclohexane ring undergoes partial hydrolysis
The −C≡N group becomes a −CONH2​ group.
Therefore, the intermediate product "A" is cyclohexanecarboxamide. This perfectly matches option (c).
Final Confirmation
Complete Hydrolysis
To ensure our deduction is flawless, let's examine the second step. The reaction conditions now include heat (Δ) along with the aqueous acid.
When an amide is heated in an acidic medium, it undergoes complete hydrolysis. The carbon-nitrogen single bond in the amide breaks, releasing ammonia (NH3​) and leaving behind a carboxylic acid (−COOH).
R−CONH2​H2​O/H+,Δ​R−COOH+NH3​
This perfectly aligns with the final product shown in the reaction scheme, confirming that our intermediate "A" is indeed the amide.
The Way Forward
Always keep a sharp eye on the reaction conditions! If the first step had employed a strong reducing agent like lithium aluminium hydride (LiAlH4​) instead of water, the nitrile would have been reduced to a primary amine (−CH2​NH2​)
Small tweaks in reagents can completely alter the functional group's destiny.