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The total number of sp$$^2$$ hybridised carbon atoms in the major product P (a non-heterocyclic compound) of the following reaction is ______.
Correct Answer: 28
Step 1: Reduction with $$\text{LiAlH}_4$$ (excess)
The starting material is $$1,1,2,2\text{-tetracyanoethane}$$:
$$\text{(NC)}_2\text{CH}-\text{CH(CN)}_2$$
Lithium aluminum hydride ($$\text{LiAlH}_4$$) is a strong reducing agent that reduces all four nitrile ($$-\text{C}\equiv\text{N}$$) groups completely into primary amine ($$-\text{CH}_2\text{NH}_2$$) groups.
The intermediate tetra-amine formed after workup with $$\text{H}_2\text{O}$$ is:
$$\text{(H}_2\text{NCH}_2)_2\text{CH}-\text{CH}(\text{CH}_2\text{NH}_2)_2$$
Step 2: Reaction with Acetophenone (excess)
Acetophenone ($$\text{Ph}-\text{CO}-\text{CH}_3$$) reacts with primary amines ($$-\text{NH}_2$$) via a nucleophilic addition-elimination reaction to form imines ($$-\text{N}=\text{C}\langle$$):
$$\text{R}-\text{NH}_2 + \text{O}=\text{C}(\text{CH}_3)\text{Ph} \longrightarrow \text{R}-\text{N}=\text{C}(\text{CH}_3)\text{Ph} + \text{H}_2\text{O}$$
Since acetophenone is in excess, all four primary amine groups will react to form four imine groups in the final product $$P$$.
Step 3: Counting $$\text{sp}^2$$ Hybridised Carbon Atoms
Let's analyze the hybridization of carbons in one attached acetophenone-derived unit ($$-\text{N}=\text{C}(\text{CH}_3)\text{Ph}$$):
$$\text{Number of sp}^2\text{ carbons per unit} = 1 + 6 = 7$$
$$\text{Total number of sp}^2\text{ hybridised carbons} = 4 \times 7 = \mathbf{28}$$
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