Scribd Logo
Upload

Welcome to Scribd!

  • 4 views

    Enantiomers

    Uploaded by

    jenald.cunanan

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd

    Enantiomers

    Uploaded by

    jenald.cunanan
    4 views4 pages

    Copyright

    © © All Rights Reserved

    Available Formats

    DOCX, PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    4 views4 pages

    Enantiomers

    Uploaded by

    jenald.cunanan

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    of 4

    Enantiomers Molecular Chirality: Enantiomers

     Enantiomers: non-superimposable
    mirror image isomers.
     Enantiomers are related to each other
    much like a right hand is related to a left
    hand
     Enantiomers have identical physical
    properties, i.e., bp, mp, etc.
     Chirality (from the Greek word for
    hand). Enantiomers are said to be
    chiral.

    Molecules are not chiral if they contain a plane


    of symmetry: a plane that cuts a molecule in
    half so that one half is the mirror image of the
     Stereochemistry - three-dimensional other half. Molecules (or objects) that possess a
    arrangement of atoms (groups) in space mirror plane of symmetry are superimposable
     Stereoisomers: molecules with the on their mirror image and are termed achiral.
    same connectivity but different
    arrangement of atoms (groups) in space The Chirality Center

    A molecule containing a carbon with four


    different groups results in a chiral molecule, and
    the carbon is referred to as a chiral, or
    asymmetric, or stereogenic center.

    Enantiomers: non-superimposable mirror image


    isomers
    Symmetry in Achiral Structures - Any molecule tetrahedral carbon is represented by two
    with a plane of symmetry or a center of crossed lines:
    symmetry must be achiral.

    Properties of Enantiomers -In general,


    Optical Activity - molecules enriched in an
    enantiomers have the same physical properties
    enantiomer will rotate plane polarized light are
    (bp, mp, density, etc). Enantiomers will rotate
    said to be optically active. The optical rotation is
    plane polarized light the same magnitude (α)
    dependent upon the substance, the
    but in opposite directions (+ or -).
    concentration, the path length through the
    sample, and the wavelength of light.

    Enantiomers can have significantly different


    Plane polarized light: light that oscillates in only biological properties
    one plane

    LINEAR ALKANES: You should draw the carbon


    backbone in the plane of the paper, and draw
    substituents either coming towards you (with
    wedges) or going away from you (with dashes).
    Note that each carbon should look like a
    tetrahedron.

    Fischer Projections - representation of a three-


    dimensional molecule as a flat structure. A
    Chiral molecules with two chirality centers meso tartaric acid: The groups on the top
    carbon reflect (through the symmetry plane)
    onto the groups on the bottom carbon.

    What is the relationship between these


    stereoisomers?

    (2R,3R) and (2S,3S) are enantiomers

    (2R,3S) and (2S,3R) are enantiomers

    Diastereomers: non-mirror image


    stereoisomers. Occurs when more than one
    chiral centers are present in a molecule. A Brief Review of Isomerism

    Isomers: compounds with the same chemical


    formula, but different arrangement of atoms
    Constitutional isomer: have different
    connectivities (not limited to alkanes)
    Stereoisomers: Atoms connected in the same
    way, but different
    three-dimensional arrangement of atoms or
    groups (topology)
    Achiral Molecules with Two Chirality Centers
    enantiomers: non-superimposable mirror
    image isomers
    diastereomers: non-superimposable, non-
    mirror image isomer (more than one chiral
    Meso: molecules that contain chiral atoms but center.
    are achiral because they also possess a plane of geometric isomers (diastereomers): E / Z alkene
    symmetry. isomers

    You might also like