Molecular Representations 11.12.2022

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Converting between Bond-Line, Lewis and Condensed structures

Chemical Formulas show only the composition of a molecule:


Converting Condensed Structure to a Bond-Line Structure
C4H10, C6H6O, C7H10N, C3H9NOS.

Lewis structures are the electron dot representations for molecules. This is the bond-line structure of molecule A that was shown before:
- The Lone Pairs of electrons are shown as dots.
- The Bonds are shown as dots or solid lines.
Let's convert it from Partially Condensed to Bond-Line structure following these steps:

1) Number all the atoms (except for H's).


Note: Numbering atoms will help you immensely for doing any transformation in Organic Chemistry. It
does not have to be in a particular order or following the IUPAC rules.
In Condensed structures, all the atoms are shown while the bonds are omitted:

2) Simply connect all the atoms from left to right.


Note that some connections maybe wrong at this point. We will fix them in the next step.
Groups that are repeating in a row may be put in parentheses:

Follow the table for standard valencies on the bottom-left to identify the wrong connections:

In Partially Condensed Structures, some bonds (mostly in functional groups)


are still shown as solid lines:
3) Rearrange the atoms such that they have correct number of bonds: (It will be very
beneficial to learn the functional groups at this point)

Skeletal (Bond-line, Zig-Zag) Structures

This is the most common and important way of drawing molecules in Organic Chemistry! These are the only ways to have correct number of bonds and lone pairs.
You must learn to understand and convert any molecular representation into a bond-line Again, knowing the functional groups will make it much easier to put the atoms in right places.
structure.
To interpret a bond-line structure, assume that: 4) Draw the carbon chain in a zig-zag form.
1) There is a carbon at each junction (corner) and periphery Putting the first atom up or down doesn't matter as long as you keep the correct connectivity of atoms.
2) Each carbon has enough hydrogens to have 4 bonds (unless
there is a formal charge)

5) Erase the carbon atoms together with the hydrogens on them.


Keep all the heteroatoms (any atom except carbon) together with the hydrogens on them.

Aldehydes are usually shown with this hydrogen.

Functional groups - not obvious to recognize in condensed structurers:

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Doing practice problems is the only way to learn - https://www.chemistrysteps.com/converting-bond-line-lewis-condensed-structures/ gevorg@chemistrysteps.com

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