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Basic IUPAC Organic Nomenclature

First point of difference rule

This is probably the most difficult of the rules associated with nomenclature to master.

The factors that influence the numbering according to the first point of difference rule are:

Misconception Alert!
It is often INCORRECTLY taught in High School that it is the lowest sum of locants that determines the numbering scheme.

See here for more discussion on the first point of difference rather than summing locants follow this link.

STUDY TIP
In order to work with the first point of difference rule, try the approach shown below based on the comparision of 1,1,2 vs 1,2,2:

  • for each possible numbering scheme, list out the locants in numerical order
  • compare the "lists" to locate the first point of difference, i.e. the first time you encounter a low number
  • at the first point of difference, select the lower locant choice (mouseover)

 

example
how to determine the first point of difference


Here are some illustrative examples of the first point of difference and related rules:

2-methylpentane
not
4-methylpentane.
difference rule
Here the methyl group is given the lowest number by numbering as shown (2- rather than 4-).
2,2,4-trimethylpentane
not

2,4,4-trimethylpentane

difference rule
The first difference is at the second locant - by numbering as shown this is kept lower (2- rather than 4-).
2,4,4-trimethylhexane
not
3,3,5-trimethylhexane
difference rule
The first difference is at the first locant - by numbering as shown this is kept lower (2- rather than 3-).
1-ethyl-2-methylcyclohexane
not
2-ethyl-1-methylcyclohexane
or
1-ethyl-6-methylcyclohexane

difference rule
The first difference is at the second locant (2- rather than 6-) which means 1,2- is preferred over 1,6-.
The application of this numbering is then dictated by the alphabetisation : ethyl preceeds methyl so ethyl gets the lower number.

pentan-2-ol
not
pentan-4-ol
difference rules
Here the principle functional group, the alcohol -OH is give the lowest locant by numbering as shown (2- rather than 4-).
pentan-3-ol
no choice !
difference rules
No matter which way this is numbered, the -OH is at C3.
4-methylpentan-2-ol
not
2-methylpentan-4-ol
difference rules
The first difference is in the -OH locant - by numbering as shown this is kept lower (2- rather than 4-).
2-methylpentan-3-ol
not
4-methylpentan-3-ol
difference rules
The first difference is in the methyl locant - since the -OH must be at C3 either way, but by numbering as shown the methyl locant kept lower (2- rather than 4-).



organic chemistry ©Dr. Ian Hunt, Department of Chemistry University of Calgary