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Tutorial queshers Set 1

| Why does molecule become a chiral if has a Plane of symmetry even through it has stereocenter​

User Candyfloss
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Answer:

Here's what I get.

Step-by-step explanation:

Consider the molecule shown below.

It has two chiral centres, labelled R and S, and an internal mirror plane that makes the right and left halves of the molecule mirror images of each other.

If we pass a beam of plane-polarized light through the sample, the R portion of the molecule will rotate the light in a certain direction.

However, the S portion will rotate the light by the same amount in the opposite direction.

The two effects cancel each other, so the molecule has no net effect on plane-polarized light.

Even though the molecule has two chiral centres, it is achiral because it has an internal plane of symmetry.

Tutorial queshers Set 1 | Why does molecule become a chiral if has a Plane of symmetry-example-1
User PaF
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