Question Details

The total number of sp2 hybridised carbon atoms in the major product P (a non-heterocyclic compound) of the following reaction is:

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Correct Answer :

28

Solution :

The correct answer is 28.

Step 1: Understand the given reaction sequence
The reaction starting material is ethane-1,1,2,2-tetracarbonitrile, which contains four nitrile groups (−CN).

The reaction steps are as follows:

1. Reduction with excess LiAlH4, followed by H2O:
Lithium aluminium hydride (LiAlH4) reduces all four nitrile (−CN) groups to primary amine groups (−CH2NH2).
Thus, reduction converts the compound into a tetraamine: butane-1,2,3,4-tetraamine derivative, having four −CH2NH2 groups attached to the central C−C backbone.

2. Reaction with excess Acetophenone:
Acetophenone is Ph−CO−CH3 (C6H5COCH3). Primary amines react with carbonyl compounds (ketones/aldehydes) to form imines (Schiff bases):

R - NH 2 + O = C ( CH 3 ) Ph R - N = C ( CH 3 ) Ph + H 2 O

Since there are 4 primary amine groups and excess acetophenone is used, all four amine groups condense with four molecules of acetophenone to form a tetra-imine product P (a non-heterocyclic compound).

Step 2: Structure of Product P
Product P contains four imine units attached to the aliphatic core:

Structure of P: [ Ph - C ( CH 3 ) = N - CH 2 ] 2 CH - CH [ CH 2 - N = C ( CH 3 ) Ph ] 2

Step 3: Count the total number of sp2 hybridised carbon atoms in P
Let us analyze each part of product P:

1. Phenyl rings (Ph = C6H5):
Each phenyl ring contains 6 sp2 hybridised carbon atoms.
Since 4 acetophenone molecules reacted, there are 4 phenyl rings in P.
Total sp2 carbons from phenyl rings = 4 × 6 = 24.

2. Imine carbons (−N=C(CH3)Ph):
The carbon involved in the imine double bond (−N=C−) is sp2 hybridised.
There are 4 imine groups in P, so there are 4 imine sp2 carbon atoms.
Total sp2 carbons from imine groups = 4 × 1 = 4.

3. Other carbons in the molecule:
- Methyl carbons attached to imine (−CH3) are sp3 hybridised.
- Methylene carbons (−CH2−) and central CH carbons of the core are sp3 hybridised.

Step 4: Final Summation
Total number of sp2 hybridised carbon atoms = (4 phenyl rings × 6 sp2 carbons) + (4 imine sp2 carbons) = 24 + 4 = 28.

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