Quick (and maybe dumb) question on chirality

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In summary, the question is asking why the hands are not constitutional isomers. The conversation explains that they are actually stereoisomers, meaning they have the same molecular formula but a different 3D orientation. The hands are not constitutional isomers because they are mirror images and not different structures, as required for constitutional isomers.
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Homework Statement



How are my hands not constitutional isomers?



The Attempt at a Solution



I read this in a book today (Organic Chemistry for Dummies - good book actually), and I was covering chirality. Now, I am a bit shaky on it and need to go over it, but I got stuck on this for a while. The author stated that your hands are stereoisomers rather than consitiutional isomers.

Here is my thought process...

A constitutional isomer has the same molecular formula but some of the atoms are not in the same location. A stereoisomer is a molecule with the same molecular formula but a different 3D orientation.

Now, for my point. My hands have the same molecular formula (4 fingers and one thumb). The thumb and pinky are not structurally in the same place from hand to hand. Isn't that what a constitutional isomer is? I mean, my hand still has the same molecular formula but just a different structure. It's like comparing butane to methylpropane, different structure but still an isomer.

So what am I missing?
 
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  • #2
Mirror image.

Actually, if you will list your fingers starting from thumbs, you will find out that both hands are identical - even if obviously they are not.

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  • #3
Switch your thumb and your middle finger. Compare this constitutional isomer with the other hand. Not mirror images yet they have the same formula (4 fingers, 1 thumb).

Compare your unaltered hands. Mirror images but not constitutional isomers. Middle finger in middle... thumb off by itself, etc. These are stereoisomers.
 
  • #4
Thanks guys, I got it!
 

1. What is chirality?

Chirality is a term used in chemistry to describe the property of a molecule to exist in two non-superimposable mirror image forms, also known as enantiomers.

2. Why is chirality important in chemistry?

Chirality plays a crucial role in many biological processes and chemical reactions. It affects the physical and chemical properties of molecules, such as their melting point, boiling point, and reactivity. Chirality also has implications in drug design and development, as different enantiomers of a drug can have different effects on the body.

3. How is chirality determined in a molecule?

Chirality is determined by the arrangement of atoms and groups around a central carbon atom, also known as the chiral center. If the four groups attached to the chiral center are arranged in a specific sequence, the molecule is chiral.

4. What is the difference between chirality and symmetry?

Chirality and symmetry are opposite concepts. A molecule is chiral if it does not have a plane of symmetry or a center of symmetry. In contrast, a molecule is symmetrical if it has a plane of symmetry or a center of symmetry.

5. Can a molecule have more than one chiral center?

Yes, a molecule can have multiple chiral centers, resulting in the possibility of having multiple stereoisomers. The number of possible stereoisomers in a molecule with multiple chiral centers is determined by the formula 2^n, where n is the number of chiral centers.

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