How do you name an alkene using IUPAC rules if the longest carbon chain in this alkene does not include the double bond?

Question

For example, which is the right way to name this compound:

Is it 2-bromo-4-methylenehexane or 4-bromo-2-ethylpent-1-ene?

Does the larger number of carbon in a chain take priority, as in the former, or does the carbon-carbon double bond take priority, as in the latter?

Answer 1

The IUPAC recommendations on this matter have been changed. In the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), the order of seniority between unsaturation and length of chain given in earlier recommendations is reversed:

(…), the first criterion to be considered in choosing a preferred parent acyclic chain is the length of the chain; unsaturation is now the second criterion.

For example, a preferred IUPAC name is 3-methylidenehexane (not 2-ethylpent-1-ene) since the longer chain now supersedes a shorter unsaturated chain. (This example is given in the Blue Book.)

Besides, the prefix ‘methylene’ is no longer recommended in IUPAC nomenclature to designate the $\ce{=CH2}$ group. The preferred prefix is ‘methylidene’.

Therefore, the correct name for your example is 2-bromo-4-methylidenehexane.

Answer 2

From wikipedia:

Identification of the parent hydrocarbon chain. This chain must obey the following rules, in order of precedence:

1. It should have the maximum number of substituents of the suffix functional group. By suffix, it is meant that the parent functional group should have a suffix, unlike halogen substituents. If more than one functional group is present, the one with highest precedence should be used.

So the alkene takes priority over the alkane and 4-bromo-2-ethylpent-1-ene is the correct name.