Explain handedness of molecules with a chiral center

Reference no: EM13171900

A center of chirality (from the Greek cheir, hand) imparts the property of handedness to a molecule. In this part of the experiment, the left- or right- handedness of molecules with a chiral center will be illustrated with models.

A molecule is said to be chiral (that is, to have the property of handedness) if its mirror image is not superimposable. The mirror image of a left hand, for example, is a right hand. A molecule that is achiral has a mirror image that is superimposible. We shall see that any molecule with a plane of symmetry is achiral.

Procedure: Reconstruct the original model (carbon (black) with light blue ball, red, blue and, green polyhedrons attached). Set the model on the desktop so that the substituent light blue ball atom points toward the ceiling.

Looking down on the model and proceeding clockwise from the green atom, record the colors of the three atoms that rest on the desktop.

Now construct a second model that is the mirror image of the first, and place it on the desktop with the light blue ball atom up:

6. In which direction, clockwise or counterclockwise, must you proceed in order to list the same sequence of colors of the three atoms resting on the desk's surface?

a. Clockwise

b. Counterclockwise

Try to superimpose the two models.

7. The models are

a. Superimposable

b. Not superimposable

The two models that you have just constructed represent chiral molecules- they lack a plane of symmetry and have mirror images that are notsuperimposable. Two substances, the molecular structures of which are related as an object and its nonsuperimposable mirror image are called enantiomers. They differ from each other only in properties that have a direction or "handedness," such as, for example, the direction(clockwise or counterclockwise) in which they rotate a beam of plane-polarized light. Because of this latter property, such substances are sometimes called optical isomers. They are optically active.

Now we will examine the consequence of having at least two identical atoms or groups attached to a tetrahedral carbon atom.

Replace the green atom in each model with a red atom, so that each model has two identical groups attached to the central carbon atom:

8. Are the models still mirror images?

a. Yes

b. No

9. Does either of the models have a plane of symmetry?

a. Yes

b. No

10. Are the models superimposable?

a. Yes

b. No

11. Do the models represent identical molecules or different molecules?

a. Identical

b. Different

Place each model on the desk so that the light blue ball substituent points up.

12. To define the same sequence of colors for the three atoms resting on the desk top, must you proceed

a. Clockwise

b. Counterclockwise

c. Either way

13. Are the models chiral (handed)?

a. Yes

b. No

The models you have just studied represent achiral molecules. Their mirror images are identical. They are optically inactive. Any molecule that has a plane of symmetry is achiral.

Reference no: EM13171900

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