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Homework Help: Simple elementary question chiral molecule

  1. Feb 10, 2017 #1
    1. The problem statement, all variables and given/known data
    Find if a molecule is chiral or not. It is 2-chloropentane

    2. Relevant equations

    IF the mirror image is superimposable to the molecule it is not chiral.

    3. The attempt at a solution

    Well I wrote the structural formula in 2D and I thought it was not chiral.(bottom )
    But the book wrote a 3d image and concluded it is chiral.(top part of the image)
    How can I know, a priori, that the molecule is not in a plane?


  2. jcsd
  3. Feb 10, 2017 #2


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    Science Advisor
    Gold Member

    The chiral carbon in this example is an sp3 carbon, which means that it adopts a tetrahedral geometry (so it's nonplanar). For simple chiral molecules like this, you can usually identify the stereocarbon as the carbon with 4 different substituents bonded to it. This doesn't always work: some chiral molecules are axially chiral rather than chiral at a single carbon (see the helicenes for an example), and some compounds may have multiple stereocenters arranged in a way that makes the overall compound achiral (see meso compounds for an example).
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