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Basic IUPAC Organic Nomenclature

When can you drop the locant ?

According to the IUPAC rules, locants can be omitted if:

(note that some of these conditions overlap with each other).

Here are some illustrative examples that try to capture these implications of this at this "introductory organic chemistry" level:

ethanol ethanol Locant dropped unambiguous, all C atoms in the parent chain (ethane) are equivalent
propene propene Locant dropped unambiguous, C=C must be at the end of the parent chain
propan-1-ol propan-1-ol Locant can not be dropped ambiguous, -OH group could be on C1 or C2 of the parent chain (propane) which are different
propanal propanal Locant dropped unambiguous, an aldehyde must be at the end of the chain which defines C1
propan-2-one propan-2-one Locant can not be dropped

Ketones aren't restricted to ends of chains and the parent chain (propane) has two different positions.

(IUPAC specifically cites this example)

cyclohexanol cyclohexanol Locant dropped unambiguous, all positions on the parent ring (cyclohexane) are equivalent
butan-2-one
butan-2-one
Locant can not be dropped

Ketones aren't restricted to ends of chains and the parent chain (butane) has two different positions

(IUPAC specifically cites this example)

2-chloroethan-1-ol 2-chloroethanol Locants can not be dropped

View ethanol as the parent, then there are two places the substituent could be and therefore required to include both locants.

(IUPAC specifically cites this example)

cyclohexane-1,2-diol cyclohexane-1,2-diol Locants can not be dropped

With two groups on a cyclic structure both locants are required according to the IUPAC rules to distinguish 1,1-, 1,2-, 1,3- etc.

prop-2-en-1-ol prop-2-en-1-ol Locants can not be dropped With two groups on parent structure both locants are required according to the IUPAC rules to distinguish 1,1- & 1,2-.
cyclohex-2-en-1-ol cyclohex-2-en-1-ol Locants can not be dropped

With two groups on a cyclic structure both locants are required according to the IUPAC rules to distinguish 1,1-, 1,3-, 1,4- etc.

3-bromocyclohex-1-ene 3-bromocyclohex-1-ene Locants can not be dropped With two groups on a cyclic structure both locants are required according to the IUPAC rules to distinguish 1,1-, 1,3-, 1,4- etc.

(IUPAC specifically cites this example)



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