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    Organic Chemistry - Lesson 2

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    The document discusses optical isomerism in organic molecules. It defines chiral and achiral molecules and explains that chiral molecules can rotate the plane of polarized light while achiral molecules cannot. Chiral molecules have nonsuperimposable mirror images and contain an asymmetric carbon or chiral center. The two isomers of a chiral molecule are called enantiomers. The R,S system of nomenclature is used to assign the absolute configuration around chiral centers. The specific rotation of an optically active compound depends on concentration, path length, temperature and other factors. A 1:1 mixture of enantiomers is called a racemic mixture and is optically inactive. The optical purity of a substance is determined by its enanti

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    Organic Chemistry - Lesson 2

    Uploaded by

    knlsinha
    90 views17 pages
    The document discusses optical isomerism in organic molecules. It defines chiral and achiral molecules and explains that chiral molecules can rotate the plane of polarized light while achiral molecules cannot. Chiral molecules have nonsuperimposable mirror images and contain an asymmetric carbon or chiral center. The two isomers of a chiral molecule are called enantiomers. The R,S system of nomenclature is used to assign the absolute configuration around chiral centers. The specific rotation of an optically active compound depends on concentration, path length, temperature and other factors. A 1:1 mixture of enantiomers is called a racemic mixture and is optically inactive. The optical purity of a substance is determined by its enanti

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    Organic Chemistry- Lesson 2

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    The document discusses optical isomerism in organic molecules. It defines chiral and achiral molecules and explains that chiral molecules can rotate the plane of polarized light while achiral molecules cannot. Chiral molecules have nonsuperimposable mirror images and contain an asymmetric carbon or chiral center. The two isomers of a chiral molecule are called enantiomers. The R,S system of nomenclature is used to assign the absolute configuration around chiral centers. The specific rotation of an optically active compound depends on concentration, path length, temperature and other factors. A 1:1 mixture of enantiomers is called a racemic mixture and is optically inactive. The optical purity of a substance is determined by its enanti

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    © All Rights Reserved
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    Download as pdf or txt
    90 views17 pages

    Organic Chemistry - Lesson 2

    Uploaded by

    knlsinha
    The document discusses optical isomerism in organic molecules. It defines chiral and achiral molecules and explains that chiral molecules can rotate the plane of polarized light while achiral molecules cannot. Chiral molecules have nonsuperimposable mirror images and contain an asymmetric carbon or chiral center. The two isomers of a chiral molecule are called enantiomers. The R,S system of nomenclature is used to assign the absolute configuration around chiral centers. The specific rotation of an optically active compound depends on concentration, path length, temperature and other factors. A 1:1 mixture of enantiomers is called a racemic mixture and is optically inactive. The optical purity of a substance is determined by its enanti

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    Optical Isomerism

    Isomerism of Organic Molecules: Optical Isomerism

    Structural isomers:
    Different compounds; all properties
    like boiling points, melting points,
    and solubilities are different

    Geometrical isomers:
    Different compounds; all properties
    like boiling points, melting points,
    and solubilities are different

    all properties like boiling points,


    melting points, and solubilities are same

    Are they different compound?


    What is the distinguishable property?

    They interact differently with polarized light. These are called optical isomer
    Isomerism of Organic Molecules: Optical activity

    Polarized light

    Achiral Molecule: does not rotate the plane of the polarized light
    A compound that does not rotates the plane of polarization is said to be optically
    inactive.

    THIS MOLECULE Will NOT SHOW OPTICAL ISOMERISIM


    Isomerism of Organic Molecules: Optical activity

    Chiral Molecule: rotate the plane of the polarized light


    A compound that rotates the plane of polarization is said to be optically active.

    THIS MOLECULE Will SHOW OPTICAL ISOMERISIM


    If an optically active compound rotates the plane of polarization clockwise, it is
    called dextrorotatory, indicated by (+) or Dextro or d

    If an optically active compound rotates the plane of polarization


    counterclockwise, it is called levorotatory, indicated by (-) or Levo or l
    In other words, chiral compounds are optically active and achiral compounds are
    optically inactive.
    Isomerism of Organic Molecules: Enantiomer
    How do we find that a given molecule will rotate the plane of a polarized light or Not?
    Or
    how do we know that which molecule is chiral and which is achiral?

    superimposable

    nonsuperimposable

    A chiral molecule/ object has a nonsuperimposable mirror image.


    An achiral molecule/ object has a superimposable mirror image.
    Isomerism of Organic Molecules: Chirality
    What is the key difference between a chiral molecule and an achiral molecule ?

    This carbon has


    This carbon has all two same groups
    different groups

    Carbon is called
    asymmetric carbon
    or chiral center
    Chiral Molecule Achiral Molecule

    Optically active or Chiral Molecule should have


    1. one asymmetric center or chiral center and 2. nonsuperimposable mirror image
    Mark the following molecule as chiral or achiral
    Isomerism of Organic Molecules: Enantiomer
    As chiral or optically active molecule with one chiral center will have two isomers
    One isomer rotate the plane of a polarized light to right and other will rotate to left.

    nonsuperimposable mirror image

    Two isomers are called


    Enantiomers

    Need a way to name the individual stereoisomer

    Cahn, Ingold, and Prelog devised R,S System of Nomenclature to indicate the
    configuration (arrangement) of the atoms or groups about the asymmetric carbon.

    pair of enantiomers with one asymmetric carbon, one will have the R configuration
    and the other will have the S configuration.
    Isomerism of Organic Molecules: R,S Nomenclature

    1. Rank the groups (or atoms) bonded to the asymmetric carbon in order of
    priority. The atomic numbers of the directly attached to the asymmetric carbon
    determine the relative priorities.
    The higher the atomic number, the higher the priority.

    2. If the two substituents bonded to the asymmetric carbon start with the same
    atom (there is a tie), you must move outward from the point of attachment and
    consider the atomic numbers of the atoms that are attached to the tied atoms.
    Isomerism of Organic Molecules: R,S Nomenclature

    3. If an atom is doubly bonded to another atom, the priority system treats


    it as if it were singly bonded to two of those atoms. If an atom is triply bonded to
    another atom, the priority system treats it as if it were singly bonded to three of
    those atoms.

    4. If two atoms have substituents of the same priority, higher priority is assigned
    to the atom with more of these substituents.
    Isomerism of Organic Molecules: R,S Nomenclature

    A larger group (i.e., more atoms) may not necessarily have a higher priority over
    another (smaller) group.

    5. In the case of isotopes (atoms with the same atomic number, but different
    mass numbers), the mass number is used to determine the relative priorities.
    CHD has higher priority than CH2

    Example:

    (1) (1)

    (2) (2)
    (4) (4)

    (3) (3)
    Isomerism of Organic Molecules: R,S Nomenclature

    Draw a curved arrow from 1 to 2 to 3 and back to 1 and note which direction this
    arrow goes, clockwise (cw) or counterclockwise (ccw)

    If the lowest priority group in behind the plane of the molecule, clockwise is R
    and counter-clockwise is S

    If the lowest priority group is in front of the plane of molecule, then the
    assignment is reversed: clockwise is S and counterclockwise is R

    (1) (1)
    S R
    (2) (2)
    (4) (4)

    (3) (3)

    Counterclockwise
    lowest priority group is behind of the plane clockwise
    lowest priority group is behind of the plane
    Isomerism of Organic Molecules: R,S Nomenclature
    Isomerism of Organic Molecules: Specific rotation
    optically active compound will rotate the plane of polarization

    Observed rotation () is
    measured in degrees.

    The observed rotation depends on the concentration of the sample and the length
    of the sample tube. The observed rotation also depends on the temperature,
    the wavelength of the light source and solvent.

    For a given temperature T and given wavelength


    Ovserved rotation is related with specific rotation as
    l = length (dm) of sample tube
    c = concentration (g mL-1 )of molecule
    The specific rotation is the number of degrees of rotation caused by
    a solution of 1.0 g of the compound per mL of solution in a sample
    tube 1.0 dm long at a specified temperature and wavelength.
    Specific rotation is specific to the molecule.
    Isomerism of Organic Molecules: Specific rotation
    A solution of 2.0 g of (+)-glyceraldehyde in 10.0 mL of water was placed in a 10
    cm polarimeter tube. Using the sodium D line, a rotation of +1.74o was observed
    at 25 oC. Calculate the specific rotation of (+)-glyceraldehyde.

    = + 1.74/(0.2 X 1) = + 8.7

    R or the S configuration does not tell us the direction the compound rotates
    the plane of polarization

    For some compounds with the R configuration rotate the plane to the right
    and some rotate the plane to the left

    We can tell by looking at the structure of a compound whether it


    has the R or the S configuration

    One can tell whether a compound is dextrorotatory or


    levorotatory only after measurement of optical rotation
    in a polarimeter
    Isomerism of Organic Molecules: Optical Purity
    a 1:1 mixture of opposite enantiomers is called a racemic mixture
    a racemic mixture is optically inactive( = 0)

    a optically inactive sample can be either an achiral substance or a racemic


    mixture

    If the mixture contain one of the enantiomer in excess to other, the mixture will
    show optical activity

    Excess in the enantiomers is quantified by enantiomeric excess (ee)

    If a subtance contain exclussively one enantiomers, the substance is called optically


    pure substance

    enantiomeric excess = % optical purity = X 100


    Isomerism of Organic Molecules

    (-)-2-butanol has a specific rotation of - 13.5o while the specific rotation of (+)-2- butanol is
    +13.5o. Calculate the optical purity of a mixture containing (+) and (-)-2-butanol if the
    mixture has an observed rotation of 8.10o.

    Does the mixture contain more (+) or more (-)-2- butanol?

    What is the enantiomeric excess (ee) of the mixture?

    What is the ratio of two enantiomers in the mixture?


    Looking forward

    Optical Isomerism:
    compounds with more than one chiral center

    compounds having chiral center and alkene

    importance of chirality

    conformation vs configuration

    Course material will be uploaded after 17:00 h on every Tuesday @

    http://www.iitg.ac.in/ckjana/ckjana/Teaching.html

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