"

D7.2 When One “Bond” is not Enough

In space-filling models like those of ethene (C2H4) and ethyne (C2H2):

atoms appear connected, but there’s no visible indication of how many electron pairs are shared. These 3D models communicate shape and size, but not the details of electron arrangement.

That’s where Lewis structures come in. Lewis structures are built from electron bookkeeping: we assign valence electrons to atoms and connect them in ways that reflect their usual bonding patterns. Sometimes, after placing all single bonds, we find that all the valence electrons have not been used. When this happens, Lewis structures introduce multiple bonds, two or three shared electron pairs between atoms, to ensure all valence atoms are accounted for.

For example:

  • In ethene (C2H4),which has 12 valence electrons, each carbon atom bonds to two hydrogens. If there is only a single bond between the C atoms, only 10 valence electrons would be accounted for. To reach 12, each carbon shares two pairs of electrons between them. So, in Lewis structure terms, the bonding region between the two carbon atoms of ethene contain 4 electrons, which is represented as a “double bond” in the diagram.
Lewis structure of ethene, C2H4.
  • In ethyne (C2H2),which has 10 valence electrons, each carbon is bound to only one hydrogen. Placing 6 electrons in the bonding region between the carbon atoms (a “triple bond” in the diagram) is needed to have all 10 valence electrons represented in the structure.
Lewis structure of ethyne

Activity

Draw the valid Lewis structures for ethane (C2H6), ethene (C2H4), and ethyne (C2H2). What patterns do you notice in how many pairs of electrons are shared between the carbon atoms?

Draw and Write in your notebook, then left-click here for an explanation.

Lewis structures of ethane (c2h6), ethene (c2h4) and ethyne (c2h2)

All three molecules have two carbon atoms bonded to each other. As the number of hydrogen atoms that are bonded to each carbon atom decrease, the number of electron pairs shared between the carbon atoms increase.

Even though single, double, and triple bonds are conventions used in Lewis structures, they reflect real differences in molecular behavior:

  • As more electrons are shared, bond strength increases and bond length decreases.
    Average bond strength Average bond length
    C–C 346 kJ/mol 154 pm
    C=C 598 kJ/mol 134 pm
    C≡C 813 kJ/mol 121 pm
  • Double and triple bonds often restrict rotation and influence reactivity.
  • They affect electron distribution, which influences how molecules interact.

So while molecules just have bonds (electron-sharing interactions between atoms), our descriptions of those bonds (single, double, triple) are powerful tools for reasoning about structure, stability, and reactivity.

Comments
Please use this form to report any inconsistencies, errors, or other things you would like to change about this page. We appreciate your comments. 🙂 (Note that we cannot answer questions via the google form. If you have a question, please post it on Piazza.)

License

Icon for the Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License

Chem 109 Fall 2024 Copyright © by Chem 109 Team is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

Share This Book