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JEE Main 2009
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Animated Solution for Chemistry - Organic Chemistry: The alkene that exhibits geometrical isomerism is

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The Core Principle of Geometrical Isomerism

When we talk about geometrical isomerism in alkenes, we are fundamentally discussing the spatial arrangement of atoms around a rigid structure. The carbon-carbon double bond () is the star of the show here. Unlike a single bond, which allows free rotation like a wheel on an axle, a double bond is locked in place. This restricted rotation means that the groups attached to the double-bonded carbons are fixed in their relative positions.
However, restricted rotation alone is not enough! For an alkene to exhibit geometrical isomerism, it must satisfy a strict symmetry condition: Each carbon atom of the double bond must be attached to two different groups. Mathematically, if we have an alkene of the form , it will only show geometrical isomerism if $a eq b$ and $c eq d$.

Analyzing the Candidates

Let's put our four options to the test using this golden rule.
1. Propene () If we look at the rightmost carbon atom of the double bond in propene, we immediately spot a problem. It is bonded to two identical hydrogen atoms. Because swapping these two identical hydrogens doesn't create a new spatial arrangement, propene fails the test.
2. 2-methyl propene () This molecule fails spectacularly on both sides! The left carbon is attached to two identical methyl () groups, and the right carbon is attached to two identical hydrogen atoms. There is absolutely no chance for geometrical isomerism here.
3. 2-methyl-2-butene () While the right carbon of this molecule has two different groups (a hydrogen and a methyl group), the left carbon ruins the party. It is bonded to two identical methyl groups. Remember, the rule must be satisfied for both carbons independently. Thus, this option is also incorrect.

The Winning Molecule

4. 2-butene () Finally, we arrive at 2-butene. Let's inspect it carefully. The left carbon is attached to a methyl group and a hydrogen atom—these are different! The right carbon is also attached to a methyl group and a hydrogen atom—different again!
Because 2-butene perfectly satisfies our condition, it can exist in two distinct spatial forms. When the two bulky methyl groups are on the same side of the double bond, we call it the cis-isomer. When they are locked on opposite sides, we call it the trans-isomer. Therefore, 2-butene is the only alkene among the choices that exhibits geometrical isomerism.

Similar Questions

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