Drawing molecules

1. Introduction 2. Structural representation to skeletal (line) diagram

H H H O H H H O O
H C C C H
C C C H H H
C C H N H H N H N
H C H C H H H
H H H H
Organic chemists use line drawings or H H H H
skeletal structures to represent Structural diagram Intermediate stage Skeletal or line diagram
molecules. These drawings codify a lot Skeletal diagrams emphasise the First, ignore the carbon labels but Then ignore all C–H bonds, removing
information in clean, simple drawings & functional groups within a molecule. leaving the bonds so that it is clear the hydrogen labels and the bonds.
are based on Lewis structures. where the carbon atoms should be Retain all hydrogen–heteroatom bonds.

3. Clean structures 4. Skeletal diagram to full structural representation

i. Bonds coming off multiple bonds HH HH
H H
should be far apart OH C OH H H C OH H H C OH
H H H H
C C C C C C OH
CO2H C C CO2H H C C CO2H H C C C
✔ ✗ C
C
C H C
C
C H H C
C
C H O
H H H H
ii. Single bonds should be a zig-zag H H H H
Add carbon atoms Add hydrogen atoms Condensed formula

✔ ✗ The end of each line or kink in a chain is

a carbon atom - add the label
All carbon atoms have four bonds if
neutral. If less than four bonds are shown
The condensed formula shows all
atoms. You cannot add hydrogen to get
add C–H until four bonds achieved correct number of bonds. (C=4; N=3; O=2)

5. Errors 6. Conclusion
O
i. Never show just the carbon atoms. iii. Never draw a pentavalent carbon. Skeletal or line diagrams simplify
This is meaningless to a chemist. H H structures making it easy to see what CO2H C H
O
C functional groups are present.
C C NH2 NH2
C C H3C CH3 There are many ways of drawing a
H
molecule and chemists will show carbon
ii. Never remove only the hydrogen iv. Get the shape right. It is a zig-zag if O
or hydrogen atoms if they are relevant to
atoms. The end of a line is a carbon all single bonds otherwise maximise the discussion. CO2H
atom not a hydrogen. separation of bonds OH
Line diagrams also have to show three- H NH2
C C dimensional shape but that is a N
C C H H
discussion for another day. valine
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