The Hydrocarbons: Part 1 – Alkanes

1.0 Rules For Drawing Line or Skeletal Structures

- C-C bond is shown as a line

- chain of C-C bonds (non-cyclic) shown as a zigzag line
- C atoms are not shown
- H atoms bonded to C are not shown
- H atoms connected to atoms other than C are shown
- other atoms shown (eg N, O, Cl)

2.0 Draw line structures for the following molecules:

Draw line drawings for the following molecules:
3. Only one substituent:
• Number the C atoms in parent chain starting from end closest to the 1st C atom
that has a substituent:

i.e. give the substituent as low a number as possible.

• Name the substituent and designate its position on the parent chain by a
number → prefix.

• The prefix and the LCCC are joined in 1 word with a hyphen be tween
number and the substituent’s name.
4. More than one substituent:
• Always number LCCC from end closest to the 1st substituent
• Number in direction that results in lowest possible combination of numbers
in the compounds name
• List substituents in alphabetical order
• Hyphens separate numbers and words or words and numbers

• If 2 or more chains of same length then the parent is the chain with the
most substituents (called rule 6 in Bruice ed 1 and ed 2).
4.1 When substituents are the same:
• Indicate repetition by di-, tri-, tetra-
• Identical substituents each have a number, listed together, separated by commas
• Do not alphabetize di-, tri- or tetra.
4.2 When numbering in either direction leads to the same lowest number for
one of the substituents:
 the chain is numbered in the direction that gives the lowest possible number
to one of the remaining substituents.
3, 4, 7
3, 6, 7
1 3 6 7

7 4 3 1

3, 7-diethyl-4-methylnonane Not 3, 7-diethyl-6-methylnonane

5. If same substituent numbers are obtained in both directions:
- the substituent which takes priority alphabetically receives the lower number
3. Butyl groups have 4 carbon atoms and there are 4 of these alkyl groups

Note: prefixes sec and tert refer to classification of carbon atom

sec- means a 2° C atom and tert means a 3° C atom

Only learn n-butyl and tert-butyl

Take home problem 1
Write the line structure for 4-(tert-butyl)heptane
The terms primary (1°), secondary (2°), and tertiary (3°)
- routinely used in organic chemistry
- a primary carbon is attached to only one other carbon atom
- secondary carbon atoms are bonded to 2 carbon atoms
- tertiary carbon atoms are bonded to 3 carbon atoms.

Classify the carbon atoms in the following molecule: done in class

Make sure you get 5 primary C atoms, 5 secondary C atoms and 3 tertiary
C atoms.
(ii) Constitutional Isomers of C5H10
- there are 3 constitutional isomers for pentane
Take Home Problem 2
How many constitutional isomers are there for an alkane with the molecular
formula C6H12? 5

Draw and name them (use systematic nomenclature).