Introduction to Alkane Nomenclature http://masterorganicchemistry.

com

A. Determining the Priority of Functional D. Applying the Lowest Locator Rule F. Dealing With Branched Substituents
What's in a name? Groups. (the IUPAC Way)
Too big a subject to cover on one sheet! This Number the chain from one end so as to provide Treat each branched substituent as its own
paper will focus on alkanes. Determining the lowest locator possible for the first substituent. naming problem.
3-ethyl-5-(1-methylpropyl)-4,4-dimethylnonane suffix functional group priority will be the subject of
6 6 4 2 Carbon #1 of the branched substituent will be
a subsequent sheet. 2 4 5 1 where it meets the main chain.
1 3 5 7 7 3

B. Applying the Chain Length Rule •Longest chain is propyl

2 •Methyl substituents are
the NUMBERS are called "locators" 3-methyl heptane NOT 5-methyl heptane 1 3
on carbon #1
9 7 5
items in BLUE are called "substituents". 8 6 4
•Name of substituent is
the name in RED at the end is called the suffix. 3
2 This also applies for subsequent substituents, 1 2 (1,1-dimethylpropane)
1
if either direction would give the same number.
The purpose of this sheet is to demonstrate the rules by which alkanes are named.
4-ethyl-6-methylnonane 4 6 4 •Longest chain is ethyl
2 3 5 7 6 5 3 2 1
1 7
ORDER OF BUSINESS Longest chain is 9 carbons - suffix •Methyl substituent is on carbon #1
will be nonane •Name of substituent is (1-methylethyl)
A. Determine the priority of functional groups (not covered here since Watch out! Longest chain might not
2,3,6-trimethylheptane NOT 2,5,6-trimethylheptane We put the name in brackets to avoid confusing the
we're dealing with alkanes only) be drawn as a "straight chain"
numbers of the branched substituent with the numbers of
B. Find the longest linear chain of your molecule, or the largest ring (whichever is
8 3 For rings with one substituent, the locator "1" the main chain.
greatest). This is the Chain length rule which defines both the "main chain" and also 4 2
the suffix. can be dropped.
7 5 1
-tiebreaker: where more than one "path" along the molecule leads to the 6
longest chain, the main chain is the one that contains the most substituents. 2-methyloctane
C. Identify the substituents along your main chain. Substituents are classified
Longest chain is 8 carbons - suffix
according to length of carbon chain and the suffix "yl" is attached. 1 3
will be octane 2 4
D. Number your chain from one of the ends. The LOWEST LOCATOR RULE determines 7
5 9
which end is chosen as carbon #1: "Number the chain such as to provide the lowest Chains vs. rings 6 8
possible locators for the chain." methylcyclohexane the same as 1-methylcyclohexane
Rings take priority over chains, assuming there
-tiebreaker for lowest-locator rule: alphabetization are only alkyl groups in the chain. ***see note below
E. Multiple instances of substituents are given the prefixes di, tri, tetra, etc. 3-methyl 4-(1-methylethyl) 5-(1,1-dimethylpropyl) nonane
-note: must have locator for all substituents. Example: 1,1-dimethyl is correct. 1- Tiebreaker: Alphabetization
In certain instances, you may see the trivial names isopropyl,
dimethyl is incorrect. If the same locators are obtained from either isobutyl, tert-butyl, tert-pentyl used.
F. Branched substituents are numbered and named seperately from the main chain, direction of the chain, the chain is numbered
and put in brackets. according to alphabetical order of the substituents. e.g. 4-isopropyl-3-methyl-5-tert-pentylnonane.
G. The FINAL name is assembled such as to arrange the substituents in
alphabetical order. propylcyclobutane butylcyclopropane 2 4 6 6 4 2 The official IUPAC nomenclature system will never let
5 5 3 1
-"di", "tri", "tetra" are ignored for alphabetization purposes. 1 3 7 7 you down. It would probably be best to just go with that.
-prefixes like "n", "tert", "i" and "sec" are ignored for alphabetization purposes.
THE EXCEPTION is "isopropyl" and "isobutyl". For some reason these count as "i" G. Putting the Name Together.
- not covered here, but this is also where one puts in descriptors like "cis", "trans", (R), (S) Tiebreaker: Alphabetization 1. Put your substituents together in alphabetical order.
(E), (Z) and so on. Where more than one "longest chain" exists, 3-ethyl-5-methylheptane NOT 3-methyl-5-ethylheptane For alphabetization purposes:
the more substituted chain is chosen as IGNORE •"di", "tri", "tet", etc.
Names for Hydrocarbon Chains and Rings the "longest chain" • sec-, tert-, n-,
1 2 •cyclo-
DO NOT IGNORE
1 methane 6 4 2 1 • "iso". For some strange reason"isopropyl" is
3 cyclopropane 8 3
7 5 alphabetized under "i" and not "p".
2 ethane 1-ethyl-2-methylcyclobutane NOT
2 Don't ask me why.
1
3 propane 4 cyclobutane 1-methyl-2-ethylcyclobutane 2. Affix the locators.
3-ethyl-2-methyloctane
4 butane (NOT - 3-isopropyloctane) 3. Make sure any branched substituents are in brackets.
5 pentane 5 cyclopentane E. Multiples of the Same Substituent
6 hexane 4. Attach the suffix at the end.
C. Identifying Substituents Multiples of the same substituent are given the
7 heptane prefixes "di", "tri", "tetra", etc. The lowest locator
6 cyclohexane Substituents are carbon fragments branching off the rule still applies. 1
8 octane main chain. They are named according to the number 2 4
3 5 7 9
9 nonane of carbons like the main chain would be, except the 2 6 4 6 6 8
7 and higher follow 4 2
"ane" is dropped and replaced with "yl" 1 3 5 7 1 3 5 7
10 decane the same pattern.
3-ethyl-5-(1-methylpropyl)-4,4-dimethylnonane
ethyl
11 undecane
8 6 4
7 5 3 3,5-dimethylheptane 2,3,5-trimethylheptane
12 dodecane
2
20 eicosane butane heptane methyl
1 Also applies to substituents on the same carbon:
This sheet © 2010 James A. Ashenhurst
Sometimes you will see "n" in front to 1 3 5 7 http://masterorganicchemistry.com
2 4 6
indicate that it is a straight-chain alkane 3-ethyl-5-methyloctane
Errors/omissions/suggestions?
propyl james@writechem.com
n-hexane n-pentane 4,4-dimethylheptane Version 1.1, Jan 2011
6 2
7 4 3 Extremely common
5 1 NOT 4-dimethylheptane
NOT 4,4-methylheptane mistakes!
Trivial names for substituents 4-propylheptane For more comoplete resources on nomenclature consult:
R R R R R 1) "Organic Chemistry Online" by William Reusch:
( )n ( )n ( )n ( )n ( )n http://www2.chemistry.msu.edu:80/faculty/reusch/VirtTxtJml/intro
1.htm
*** there seems to be some degree of confusion 2) IUPAC "Blue Book"
isopropyl sec-butyl isobutyl on this point. Both "1-butylcyclopropane" and http://www.acdlabs.com/iupac/nomenclature/
tert-butyl tert-pentyl "1-cyclopropylbutane" are commonly used. If
someone can clarify, please write me.