Quick (and maybe dumb) question on chirality

  • Thread starter Thread starter Attraction
  • Start date Start date
  • Tags Tags
    Chirality
Click For Summary

Discussion Overview

The discussion revolves around the concept of chirality and the classification of isomers, specifically addressing why human hands are considered stereoisomers rather than constitutional isomers. Participants explore the definitions and characteristics of these types of isomers in the context of a homework question.

Discussion Character

  • Homework-related, Conceptual clarification, Debate/contested

Main Points Raised

  • One participant defines constitutional isomers as having the same molecular formula but different atom arrangements, while stereoisomers have the same formula but different 3D orientations.
  • Another participant suggests that both hands are identical when fingers are listed from thumbs, implying that they are not constitutional isomers.
  • A different participant proposes a comparison by switching fingers, indicating that while the altered hands are not mirror images, they still share the same formula, challenging the classification of isomers.
  • Participants clarify that unaltered hands are mirror images and thus are stereoisomers, contrasting with the definition of constitutional isomers.

Areas of Agreement / Disagreement

Participants generally agree that hands are stereoisomers, but there is some debate regarding the definitions and implications of constitutional versus stereoisomers, particularly in the context of physical manipulation of the hands.

Contextual Notes

The discussion includes assumptions about the definitions of isomers and the interpretation of physical arrangements, which may not be universally agreed upon. There are also unresolved nuances in how participants relate the concepts to the physical characteristics of hands.

Attraction
Messages
28
Reaction score
0

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?
 
Physics news on Phys.org
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.

--
 
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.
 
Thanks guys, I got it!
 

Similar threads

  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 1 ·
Replies
1
Views
5K
  • · Replies 3 ·
Replies
3
Views
2K
  • · Replies 3 ·
Replies
3
Views
3K
Replies
20
Views
5K
  • · Replies 8 ·
Replies
8
Views
8K
  • · Replies 3 ·
Replies
3
Views
4K
  • · Replies 3 ·
Replies
3
Views
28K
  • · Replies 29 ·
Replies
29
Views
3K
Replies
90
Views
12K