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  • In the early days of organic chemistry,

  • chemists understood that molecules were made of atoms

  • connected through chemical bonds.

  • However, the three-dimensional shapes of molecules

  • were utterly unclear, since they couldn't be observed directly.

  • Molecules were represented using simple connectivity graphs

  • like the one you see here.

  • It was clear to savvy chemists of the mid-19th century

  • that these flat representations couldn't explain

  • many of their observations.

  • But chemical theory hadn't provided a satisfactory explanation

  • for the three-dimensional structures of molecules.

  • In 1874, the chemist Van't Hoff published a remarkable hypothesis:

  • the four bonds of a saturated carbon atom

  • point to the corners of a tetrahedron.

  • It would take over 25 years

  • for the quantum revolution to theoretically validate his hypothesis.

  • But Van't Hoff supported his theory using optical rotation.

  • Van't Hoff noticed that only compounds containing a central carbon

  • bound to four different atoms or groups

  • rotated plane-polarized light.

  • Clearly there's something unique about this class of compounds.

  • Take a look at the two molecules you see here.

  • Each one is characterized by a central, tetrahedral carbon atom

  • bound to four different atoms:

  • bromine, chlorine, fluorine, and hydrogen.

  • We might be tempted to conclude that the two molecules

  • are the same, if we just concern ourselves with what they're made of.

  • However, let's see if we can overlay the two molecules

  • perfectly to really prove that they're the same.

  • We have free license to rotate and translate both of the molecules

  • as we wish. Remarkably though,

  • no matter how we move the molecules,

  • we find that perfect superposition is impossible to achieve.

  • Now take a look at your hands.

  • Notice that your two hands have all the same parts:

  • a thumb, fingers, a palm, etc.

  • Like our two molecules under study,

  • both of your hands are made of the same stuff.

  • Furthermore, the distances between stuff in both of your hands are the same.

  • The index finger is next to the middle finger,

  • which is next to the ring finger, etc.

  • The same is true of our hypothetical molecules.

  • All of their internal distances

  • are the same. Despite the similarities between them,

  • your hands, and our molecules,

  • are certainly not the same.

  • Try superimposing your hands on one another.

  • Just like our molecules from before,

  • you'll find that it can't be done perfectly.

  • Now, point your palms toward one another.

  • Wiggle both of your index fingers.

  • Notice that your left hand looks as if it's looking

  • in a mirror at your right.

  • In other words, your hands are mirror images.

  • The same can be said of our molecules.

  • We can turn them so that one looks at the other

  • as in a mirror. Your hands - and our molecules -

  • possess a spatial property in common called chirality,

  • or handedness.

  • Chirality means exactly what we've just described:

  • a chiral object is not the same as its mirror image.

  • Chiral objects are very special in both chemistry and everyday life.

  • Screws, for example, are also chiral.

  • That's why we need the terms right-handed and left-handed screws.

  • And believe it or not, certain types of light

  • can behave like chiral screws.

  • Packed into every linear, plane-polarized beam of light

  • are right-handed and left-handed parts

  • that rotate together to produce plane polarization.

  • Chiral molecules, placed in a beam of such light,

  • interact differently with the two chiral components.

  • As a result, one component of the light gets temporarily slowed down

  • relative to the other. The effect on the light beam

  • is a rotation of its plane from the original one,

  • otherwise known as optical rotation.

  • Van't Hoff and later chemists realized that the chiral nature

  • of tetrahedral carbons can explain this fascinating phenomenon.

  • Chirality is responsible for all kinds of other fascinating effects

  • in chemistry, and everyday life.

  • Humans tend to love symmetry

  • and so if you look around you, you'll find that chiral objects

  • made by humans are rare.

  • But chiral molecules are absolutely everywhere.

  • Phenomena as separate as optical rotation,

  • Screwing together furniture,

  • and clapping your hands

  • all involve this intriguing spatial property.

In the early days of organic chemistry,

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TED-ED】キラリティとは何か、なぜ自分の分子の中にキラリティが入ってきたのか?- マイケル・エバンス (【TED-Ed】What is chirality and how did it get in my molecules? - Michael Evans)

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    稲葉白兎 に公開 2021 年 01 月 14 日
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