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Chapter 3 - Stereoisomerism and Chirality 

  • A mirror image is an object's reflection in a mirror.

    • When you look in the mirror, you see your own reflection, or mirror image.

    • Assume your mirror image is now a three-dimensional thing.

    • Then we may question, "What is your connection with your mirror image?" Instead of asking, "Can your reflection be superposed on (put on top of) the actual 'you' in such a manner that every aspect of the reflection matches perfectly to the original?"

    • The explanation is that if details are provided, you and your mirror counterpart are not superposable.

  • For example, if you have a ring on your right hand's little finger, your mirror image has the same ring.

    • Archircal: an object that lacks chirality; an object that has no handedness.

    • Molecules are small things with sizes ranging from few to hundreds of Angstroms, but they have distinct forms and geometries, as covered in the preceding two chapters.

    • Because of these characteristics, certain molecules are chiral objects.

  • It is easier to identify whether a molecule is chiral by first determining whether it is achiral.

    • To determine whether a molecule is achiral, we seek for symmetries in it.

    • We can conclude that the molecule is chiral if these symmetries are lacking.

    • If an item or molecule possesses one or more of particular symmetry components, it is said to be achiral.

    • The plane and center of symmetry are the most prevalent such components in organic molecules.

  • Any object or molecule having any of these symmetry components is achiral and may be superposed on its mirror counterpart, as we will show.

    • A plane of symmetry is an imaginary plane that divides an item or molecule so that one half is the reflection of the other.

  • The image attached below depicts a cube with numerous planes of symmetry. Both the beaker and the bromochloromethane chemical

    • Plane of symmetry: refers to an imaginary plane that is passing through an object dividing it so that one half is the mirror image of the other half.

  • Because stereoisomers are either diastereomers or enantiomers, we may also apply these terminology to conformational isomers.

    • Because they are not mirror reflections, the gauche and anti forms of butane are diastereomers.

  • Butane's two gauche forms are enantiomers because they are mirror images and cannot be superposed (see the reflection in the mirror provided).

    • As a result, these butane forms are chiral.

    • Butane, on the other hand, is not a chiral molecule since these three isomers interconvert relatively quickly at normal temperature and because they interconvert via the anti isomer, which is achiral (refer back to the image attached below to see the interconversion).

    • Because there is a plane of symmetry when all four carbons are planar, the anti isomer is achiral.

    • This debate emphasizes a crucial point: chirality may exist in molecules that lack chiral centers.

    • This situation is caused by conformational isomerism, however it is less prevalent than chirality caused by configurational isomerism.

  • When the barrier to interconversion is high, as in butane, and the enantiomers cannot interconvert at room temperature via a planar form, the molecule is chiral and the enantiomers may be separated.

  • Here's an example of a substituted biphenyl.

    • There are significant nonbonded interactions in the planar conformer due to the massive groups on the rings, and the twisted forms illustrated have much lower energies.

    • The nonbonded interactions provide an extremely high barrier to rotation around the carbon-carbon single bond that connects the rings, resulting in very sluggish rotation.

    • Despite the fact that this molecule lacks a chiral core, the mirror images are not superposable, indicating that the molecule is chiral.

  • Atropisomers are isomers that lack a chiral center yet do not interconvert due to impeded rotation.

    • Atropisomers: refers to enantiomers that lack a chiral center and differ because of hindered rotation.

Chapter 3 - Stereoisomerism and Chirality 

  • A mirror image is an object's reflection in a mirror.

    • When you look in the mirror, you see your own reflection, or mirror image.

    • Assume your mirror image is now a three-dimensional thing.

    • Then we may question, "What is your connection with your mirror image?" Instead of asking, "Can your reflection be superposed on (put on top of) the actual 'you' in such a manner that every aspect of the reflection matches perfectly to the original?"

    • The explanation is that if details are provided, you and your mirror counterpart are not superposable.

  • For example, if you have a ring on your right hand's little finger, your mirror image has the same ring.

    • Archircal: an object that lacks chirality; an object that has no handedness.

    • Molecules are small things with sizes ranging from few to hundreds of Angstroms, but they have distinct forms and geometries, as covered in the preceding two chapters.

    • Because of these characteristics, certain molecules are chiral objects.

  • It is easier to identify whether a molecule is chiral by first determining whether it is achiral.

    • To determine whether a molecule is achiral, we seek for symmetries in it.

    • We can conclude that the molecule is chiral if these symmetries are lacking.

    • If an item or molecule possesses one or more of particular symmetry components, it is said to be achiral.

    • The plane and center of symmetry are the most prevalent such components in organic molecules.

  • Any object or molecule having any of these symmetry components is achiral and may be superposed on its mirror counterpart, as we will show.

    • A plane of symmetry is an imaginary plane that divides an item or molecule so that one half is the reflection of the other.

  • The image attached below depicts a cube with numerous planes of symmetry. Both the beaker and the bromochloromethane chemical

    • Plane of symmetry: refers to an imaginary plane that is passing through an object dividing it so that one half is the mirror image of the other half.

  • Because stereoisomers are either diastereomers or enantiomers, we may also apply these terminology to conformational isomers.

    • Because they are not mirror reflections, the gauche and anti forms of butane are diastereomers.

  • Butane's two gauche forms are enantiomers because they are mirror images and cannot be superposed (see the reflection in the mirror provided).

    • As a result, these butane forms are chiral.

    • Butane, on the other hand, is not a chiral molecule since these three isomers interconvert relatively quickly at normal temperature and because they interconvert via the anti isomer, which is achiral (refer back to the image attached below to see the interconversion).

    • Because there is a plane of symmetry when all four carbons are planar, the anti isomer is achiral.

    • This debate emphasizes a crucial point: chirality may exist in molecules that lack chiral centers.

    • This situation is caused by conformational isomerism, however it is less prevalent than chirality caused by configurational isomerism.

  • When the barrier to interconversion is high, as in butane, and the enantiomers cannot interconvert at room temperature via a planar form, the molecule is chiral and the enantiomers may be separated.

  • Here's an example of a substituted biphenyl.

    • There are significant nonbonded interactions in the planar conformer due to the massive groups on the rings, and the twisted forms illustrated have much lower energies.

    • The nonbonded interactions provide an extremely high barrier to rotation around the carbon-carbon single bond that connects the rings, resulting in very sluggish rotation.

    • Despite the fact that this molecule lacks a chiral core, the mirror images are not superposable, indicating that the molecule is chiral.

  • Atropisomers are isomers that lack a chiral center yet do not interconvert due to impeded rotation.

    • Atropisomers: refers to enantiomers that lack a chiral center and differ because of hindered rotation.

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