Scribd Logo
Upload

Welcome to Scribd!

  • 70 views

    Conformations of Alkanes

    Uploaded by

    joanne
    This document discusses conformations of alkanes, specifically ethane and butane. It explains that ethane can rotate freely about its C-C bond, resulting in different arrangements called conformations. The most stable conformation of ethane is staggered, while the highest energy is eclipsed. Butane has six important conformers - the anti conformation is most stable while eclipsed conformations have the greatest energy due to repulsive interactions between atoms. A Newman projection represents conformations by projecting the C-C bond end-on.

    Copyright:

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

    Conformations of Alkanes

    Uploaded by

    joanne
    70 views3 pages
    This document discusses conformations of alkanes, specifically ethane and butane. It explains that ethane can rotate freely about its C-C bond, resulting in different arrangements called conformations. The most stable conformation of ethane is staggered, while the highest energy is eclipsed. Butane has six important conformers - the anti conformation is most stable while eclipsed conformations have the greatest energy due to repulsive interactions between atoms. A Newman projection represents conformations by projecting the C-C bond end-on.

    Original Title

    conformations of Alkanes (1)

    Copyright

    © © All Rights Reserved

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    This document discusses conformations of alkanes, specifically ethane and butane. It explains that ethane can rotate freely about its C-C bond, resulting in different arrangements called conformations. The most stable conformation of ethane is staggered, while the highest energy is eclipsed. Butane has six important conformers - the anti conformation is most stable while eclipsed conformations have the greatest energy due to repulsive interactions between atoms. A Newman projection represents conformations by projecting the C-C bond end-on.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    70 views3 pages

    Conformations of Alkanes

    Uploaded by

    joanne
    This document discusses conformations of alkanes, specifically ethane and butane. It explains that ethane can rotate freely about its C-C bond, resulting in different arrangements called conformations. The most stable conformation of ethane is staggered, while the highest energy is eclipsed. Butane has six important conformers - the anti conformation is most stable while eclipsed conformations have the greatest energy due to repulsive interactions between atoms. A Newman projection represents conformations by projecting the C-C bond end-on.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 3

    CHM 1206 - Organic Chemistry

    Conformation of Alkanes - Newman Projection

    Conformations of ethane

    Stereochemistry is the branch of chemistry concerned with the three-dimensional aspects of


    molecules. The sigma bond in a carbon-carbon single bond is cylindrically symmetrical.
    Because of this cylindrical symmetry, rotation is possible around carbon–carbon bonds in
    open-chain molecules. In ethane, for instance, rotation around the C︎-C bond occurs freely,
    constantly changing the spatial relationships between the hydrogens on one carbon and
    those on the other.

    The different arrangements of atoms that result from bond rotation are called
    conformations, and molecules that have different arrangements are called conformational
    isomers, or conformers. Conformational isomers can be represented by a Newman
    Projection. A Newman projection views the carbon–carbon bond directly end-on and
    represents the two carbon atoms by a circle. Bonds attached to the front carbon are
    represented by lines to the center of the circle, and bonds attached to the rear carbon are
    represented by lines to the edge of the circle.

    The lowest-energy, most stable conformation is the one in which all six C︎-H bonds are as far
    away from one another as possible—staggered when viewed end-on in a Newman
    projection. The highest-energy, least stable conformation is the one in which the six C-︎H
    bonds are as close as possible— eclipsed in a Newman projection. At any given instant,
    about 99% of ethane molecules have an approximately staggered conformation and only
    about 1% are near the eclipsed conformation.
    The extra 12 kJ/mol of energy present in the eclipsed conformation of ethane is called
    torsional strain. Because a total strain of 12 kJ/mol arises from three equal hydrogen–
    hydrogen eclipsing interactions, we can assign a value of approximately 4.0 kJ/mol (1.0
    kcal/mol) to each sin- gle interaction. The barrier to rotation that results can be represented
    on a graph of potential energy versus degree of rotation, in which the angle between C︎H
    bonds on the front and back carbons as viewed end-on (the dihedral angle) goes full circle
    from 0 to 360°. Energy minima occur at staggered conformations, and energy maxima occur
    at eclipsed conformations

    Conformational Analysis of Butane

    

    If we consider rotation about the C2-C3 bond of butane, we find that there are six important
    conformers, shown as I–VI below:

    The anti conformation (I) does not have


    torsional strain from steric hindrance
    because the groups are staggered and the
    methyl groups are far apart. The anti
    conformation is the most stable. The
    methyl groups in the gauche
    conformations III and V are close enough
    to each other that the dispersion forces
    between them are repulsive; the electron
    clouds of the two groups are so close that
    they repel each other. This repulsion causes
    the gauche conformations to have
    approximately 3.8 kJ mol︎1 more energy
    than the anti conformation.

    The eclipsed conformations (II, IV, and VI)


    represent energy maxima in the potential energy diagram. Eclipsed conformations II and VI
    have repulsive dispersion forces arising from the eclipsed methyl groups and hydrogen
    atoms. Eclipsed conformation IV has the greatest energy of all because of the added large
    repulsive dispersion forces between the eclipsed methyl groups as compared to II and VI.

    You might also like